What I Learned From the “Check Your Head” Shirt



This damn t-shirt: the end of innocence. Circa 1987.

In 7th grade, fitting in was pretty much the entire game. It was 1987; despite the fact that it was 20 below on the shores of Lake Michigan, everyone dressed like they were about to go surfing. As for me, I wore whatever corduroy slacks my mother dropped on me. Then, one day, every single kid in my grade came to school wearing a t-shirt: an airplane crashing vertically into the ground.

To my eyes, this shirt was ugly (which it is, I guess) and everyone wearing it was an idiot (which they were, given that this was 7th grade). Plus: Licensed to Ill? Bad grammar.



I never fit in which trendy people like these. Perhaps to my credit.

I claimed not to want to fit in, and to some degree, I paid the price: I ate lunch with two other non-cool kids in the library. Instead of jockeying for the best seat in the cafeteria, we talked about the books we would one day write. Instead of talking about “who liked who,” we discussed our favorite sci-fi movies with the librarians (remarkably funky people for Mequon, Wisconsin).


We were happy not to fit it. But we weren’t exactly comfortable with who we were, either. Dropping out wasn’t the solution.


sheep.jpgAs an adult, I’ve made peace with License to Ill (it’s an AWESOME album), and with trends of all sorts. It helps that, as I went through my twenties and thirties, fitting in via the fad du jour, whatever form it took, became the province of people I don’t have to trouble myself with.

For the rest of us, the important “fitting in” is not about where you are or what you wear or what you listen to, it’s about fitting into your own skin. We admire (and strive to be) confident in who we are. We admire people who are comfortable with themselves, comfortable with their surroundings. And the people we really admire are the ones who make everyone else feel comfortable, as well.

And by the way, if this isn’t the way your world works, consider moving to a new world.

on point.jpgBehind the scenes, fitting in with your world is more than putting on a confident face and striding into a room like you own the place. It’s also about how you present yourself. How you “read.” And if you don’t think that’s true, consider the reoccurring dream where you’re naked in front of an audience. Oh, you know that dream? Exactly: everyone feels, to some degree, unclothed – vulnerable – with our doubts and anxieties. We do our best to dress ourselves, metaphorically, with confidence. And we can wear actual clothes, hopefully with confidence, every day.

When your clothes fit, we call it “on point.” When they fit together, we call it a great “out-fit.” It’s like, literally, you fit to the outside eye. The effect is pleasing and it ascribes characteristics to the wearer: you’re put together You fit.

And then there’s fitting the scenario: the perfect suit to an interview, the perfect blazer for a first date, the perfect outfit to a bar-b-q. You are in harmony with your surroundings.


Then, there are the seasons. To some, it’s always khakis and button-shirt season. But seasons give us an opportunity to stand out for fitting in – not with fashion trends, but with the world around us.

Below, I show how dressing to fit in with winter includes colors, materials, and layers.



Outfit One: #Tweed is the Tweet

To begin with, this outfit features a few “all-year” items: Levi’s (more than “all year” – they’re like “every damn day”), Clark’s Original Desert Boots, and a denim jacket.

Then, two “signifiers” indicate: “Yes, I know very well what season it is.”

  1. The tie.
  2. The vest.

Both of them are made of heavy tweed, a heavy material who comes out to play during the cold months. Obviously, the tweed tie isn’t going to keep me warm when San Francisco fog coats the city in grey brrr, but it sends the message: it’s winter, and I’m cool with that.

 Outfit Two: Black Turtle Necks, Beyond Steve Jobssherpherdsuit

Here, Gabi and I are attending a party in some swanky loft. It was a suit-worthy affair – but also, after work during the coldest month of the year. No mere “dapper suit” would flip its finger to the 40-degrees-and-raining-like-hell situation outside.

This suit, to begin with, is made of a thick, shepherds check – in black and white. Paired with a black turtleneck, it’s heavy and stark (like winter) but playful, as well.

Your winter fancy-pants should be flannel, wool, and other heavier weaves. Again, no one will haul you to fashion-jail if you’re wearing khakis, but why not radiate cozy-winteriness?

Outfit 3: Ski-Lodge on the Rangewooltieandsweater

Obviously, when temperatures dip, it’s a good time to bust out the heavy sweaters. But if you wanna get dappered up, and you pair your heavy, snuggly sweater with a bar-mitzvah tie, you’re going to undo the “fitting-in-with-the-seasons” thing you’ve been working so hard on.

Fortunately, there’s knit ties from The Tie Bar.  These things are so affordable, and so beautiful, you’ll do one of those guilty “looking both ways to see if you’re in trouble” things before you whip out your credit card.

When it arrives, pair it with a cozy sweater and a denim shirt. Don’t be surprised if someone asks you to join them on a one-horse-open-sleigh.


Outfit 4: Pulling the Wool herringbone.JPG

Our last outfit demonstrates a simple principle: texture+texture=winter.

Warm weather tends to feature bolder, stripier, polka-dottier patterns. Cold weather, on the other hand, is all about texture – meaning, you don’t see it until you look closely.

From afar (like, normal, non-creepy distance), it gives the impression of thickness. And thickness fits in, beautifully, in winter.

Combine a textured tie, jacket, and pants, and you look cozy-warm and on-point.


Try some of the tricks above, and experiment with the feeling of fitting-in that comes through embracing the seasons.



Red Wing Boots: A Dorky Teenage Dilemma Resolved

pScreenshot 2015-12-29 at 3.02.54 PMHere’s an embarrassing story.

When I was in high-school, I fancied myself a bit of a hippie. I had long hair and listened to the Beatles and the Grateful Dead. I was opposed to the Gulf War and I wore paint-splattered Levi’s that had once been my father’s work-pants. I read The Autobiography of Malcolm X  and carried a suitcase with my schoolbooks on which I’d written: “The Mighty Quinn.”

One wet, winter day, hanging out with some fellow hippie neophytes, I posed a dilemma: what was truer to the hippie ideal we strove for? A) A pair of Nike high tops thathad been languishing in my closet since I’d discovered Birkenstocks, or B) a pair of my old man’s Red Wing boots, that were too large by two sizes? The sneakers fit, but the boots were so much cooler.

Striving for some sort of authentic hippie identity in early 90s Mequon, Wisconsin was already absurd. Trying to determine the most appropriate footwear for the costume is cringeworthy. And yet, it’s sort of touching. If you haven’t seen this Buzzfeed about the 10 most embarrassing pages from the 1990 JC Penney catalog, check it out. Stylistically, the early 90s were an extension of the 80s: everything was oversized, understyled. Fanny packs, mullets, slouchy-sweaters with big belts, and Zubaz pants. I like to think that at some level, I knew that the Emperor had no clothes, so to speak. All that shit was ugly, and I wanted nothing to do with it.

Also, by way of contrast: last week, the Beatles’ music was streamed 50 Million times in 48 hours. Conversely, when I was in high school, I was ribbed for listening to the Beatles. When Waldenbooks added a new book to their meager inventory, it was a given that I would buy it. These days, there’s too much to read, let alone to buy. Don’t get me wrong, I’m not complaining. When current fashion and classic style align, it’s a good thing. That’s a luxury I didn’t experience as a High School Junior.

At some level, in my teenage groping, I was looking for music that meant something, that spoke to me, that would never age or moulder in the way that Top 40 music seemed to. I was looking for something with substance, with style, with soul. So, too, footwear.




Dapper Americana: paired with denim jacket and gingham shirt/tie.

25 years later, in preparation for spending the holidays in Milwaukee, I decided to splurge on a pair of boots that could handle a type of precipitation we don’t have out in California: “Wintery Mix.” This delightful blend of slush, show, sleet and rain penetrates the seams of boots and transforms your feet into numb stumps. My usual desert boots aren’t cut out for this sort of action.



DomesticDomestic.com, a website that curates American Made goods, offers Red Wings (made in Minnesota) in a spectacular, StyleForDorks-friendly color: Indigo. I bagged a pair and I’ve worn them every day for the past two weeks. My feet stay dry and warm, I’ve gotten a ton of compliments, and here’s what impresses me the most: no matter what I wear them with, they’re perfect. Jeans and a button up. T-shirt. Cardigan and blazer. Knit tie and flower lapel.




Vintage hat and jacket. Classic everything else.

They go with everything because they’re a classic-original, a style never that never gets old.


I started listening to the Beatles when I was 15. I got my first pair of Red Wings when I was 17. I know I’ll be fans of both for a long, long time.


How to (and How Not To) Layer Up: A Polar-tech Polemic.


Do you want to be this guy? Go right ahead.

I know it’s cold out, so I’m going to be gentle, here. Very gentle, and yet quite firm.

I say, gently-but-firmly: no fleece indoors.

I know, I know. Fleece is a perfectly rational material to wear in the chilly months: it’s cold outside, it’s drafty in the office, and fleece! Fleece is the miracle cloth that keeps hikers and kayakers and volunteers at the State Park visitor’s center warm. It’s light! It’s durable! So… wear it inside!

You can. But you really shouldn’t.

Let me put on my teacher hat and explain why.

Menswear borrows from about 100 years worth of cultural context. Browse the racks in any store, and you will see items nodding towards their roots: classic Americana. Preppie. Glam Rock and Roll. Vintage rock. Outdoorsman. College professor. Worker/trucker. Urban/Streetwear. In every case, the material and the style have a story to tell, and also an aesthetic: the clean simplicity of a white t-shirt and jeans. The trim, jaunty design of a cardigan. The dignified structure of a tweed blazer. The trim sportiness of a well-fitting polo shirt. In every case, there was once a cultural context that gave it rise, but its inherent aesthetic gave it enduring life.


Fleece: performance clothing for hiking. And not for…well, anything else.

Fleece, however, was synthesized as a technical fabric. It doesn’t drape like cotton or wool, and it pills about two days after you buy it. Perhaps as a result (excepting a brief period in the late 90s when companies were hawking it as a “performance” item) it remains, to this day, a technical garment. It’s the uniform of a wooded or rocky trail, but it lacks the aesthetic of a well-made flannel.

If you could ask it: “Hey, fleece, do you WANT to be worn to the office? To a party? To a pub?”

It would say, “No, kind owner. Thank you for asking, but kindly wear me only when you’re hiking and then leave me in the bin along with my buddies, the Vasque boots and the L.L. Bean Trail Pants.” 

If I have any friends left after my anti-fleece polemic,  I’d like to share my tips on layering up for the chilly winter months.

  1. When it’s a bit chilly out, layer on a denim jacket. 

Denim stands up to a cold breeze it but won’t crimp your style, and you can pair it with pretty much anything.

rugbyovertie2. For a smart look, wear a rugby shirt over an Oxford Cloth Button Down

And over that, a tweed or corduroy blazer.

For non-stop compliments, pair the whole thing with a knit tie.

3. Look for a sweater that looks like a jacket. Or a jacket that feels like a sweater. 

sweaterbillWhatever you call it, it looks totally bad-ass. 

4. Try a baseball-jacket. 

But keep it grey, black, or navy.

baseballAnd if you think it looks good with a T-shirt and jeans, try it with an Oxford Cloth Button Down and tweed/knit tie.

5. Find a blazer made of jersey (“sweatshirt”) material.

sweatshirtblazerWear it with anything, and wear it everywhere you’d wear a sweatshirt.


Now you have five alternatives to your fuzzy vest. Choose one, and wear it all winter long.

As for your beloved polar-tech gear, by all means. Wear it wherever you want. But be aware: it starts with “No one’s around the office, I’m just gonna slip this on for a few minutes.” Then, it’s a slippery slope down the hiking trail of dorkdom. Next thing you know, you’ll be watching Perfect Strangers reruns while wearing a Spider-man Snuggie.


“What!?! It’s warm!”







Shiver me Timbers! If you’re in the market for a new pair, move fast.

timbersWhen I take clients out for a style-up, I naturally have my go-tos. All the shoes in my post, “Top 5 Styley-Casual Shoes,” are sure-things, and I often steer clients towards them before we branch out to other options.

One pair I leave off the list because, frankly, it’s out of many people’s price-point: Timberland Boot Company’s “Wodehouse.” Note: Timberland Boot Company is Timberland’s high-end line. The Wodehouse plays the Lexus to the standard tan hiker-boot’s Corolla. You get the idea.

I have a pair of these and they are among my most comfortable shoe, and the leather is beautiful.

That said: Nordstrom is selling them for more than $100 dollars off the usual price. Are they cheap? No. Are they a great value at the new price? Yes.

Get a pair. Let me know what you think.

Two Men and a Torah: Style at the Gates of Manhood


Sam and Jake with their new outfits, post Style-Up. These guys make 13 look easy. (All professional photography courtesy of Jeff Bartee, http://www.jeffbartee.com).

It’s hard to be a bar mitzvah boy. Excuse me: bar mitzvah man.

See, that’s the problem, right there. Once we’re adults, being neither-here-nor-there is cool and edgy and interesting. But at the gates of manhood (according to Jewish tradition) or teenagerhood (according to everyone else), being in-between can be a real bummer.

Consider this: in school, very little freedom of choice. Legally, almost no rights. Your heroes are at least twice your age, and you have the sense of being an adult, but only in potential. At the same time, society (and your hormones) are telling you that you’re no longer a little kid, and you stand to lose a lot of the sweet feelings of being protected you had when you were little. To makes things worse, you’re still probably still little.


On the other hand, Jewish tradition takes a bar/bat-mitzvah very seriously (in Hebrew, bat mitzvah is the feminine). There is no transition period. All the laws and customs and responsibilities of Jewish Peoplehood are suddenly on your shoulders; yesterday, all the laws of Jewish adulthood were “not yet,” and today, it’s “go time” – you are responsible, like any Jewish adult, to study Torah, to give charity, and even to play vital, communal roles: for instance, to make a prayer-quorum for a grieving neighbor. No child can do that.

You are a 13-year-old adult.

Not a picture of me-at-13 per se, but basically, a picture of me at 13.

Not a picture of me-at-13 per se, but basically, a picture of me at 13.

For a bar mitzvah man, one’s own physical appearance can present challenges. For example, in 1987, I had braces, a bowl-cut, chipmunk cheeks, and glasses with tinted lenses. Tinted lenses!  I figured that a) glasses weren’t cool, b) sunglasses were. But you can’t go around wearing sunglasses indoors, right?! So: hybrid shades.

Not cool.

Meanwhile, I had no style of my own. I wore whatever my mother bought me, and for my bar mitzvah, I figured I would don the garment of my masculine birthright: a suit. A 3-piece suit from Kohl’s “Husky boys” department. I looked like a stumpy, pre-pubescent banker.

Oy vey.

Jake and Sam, however, have more style in their pinkies than 13-year-old me had in his entire hand and arm together, wrapped in tefillin or otherwise. Jake is a very dapper, style-conscious young man with his own burgeoning Instagram following, and Sam is athletic and handsome with a killer smile. Neither has a bowl cut.

Both needed outfits: for the bar-mitzvah ceremony and for the after-party. Meet Jake and Sam.

boat leatherAlways Start With Shoes

While I’ve often said that shoes are the foundation of every outfit, for Sam and Jake, this also served as a kind of “short-hand” for what aesthetic they were looking for. In the video above, each says the same thing: that they’re looking for something stylish. But here’s where their paths diverged.

Jake chose gravitated towards Clark’s desert boots and a pair of laceless wingtips. Each shoe walks the line between fancy and casual – perfect for a Bar Mitzvah and party. (For more on high-low mashup, click here). Meanwhile, Sam admired black leather Chucks and a pair of blue boat shoes. Both (like Jake’s picks) can be dressed up or dressed down, but Sam’s choices were sportier and helped to guide the color palette of his outfit.

samblazer swetaerandscarfv2Next, we went to Zara Man. Here, we found a bohemian scarf, sweater, and patterned shirt for Jake. Meanwhile, Sam discovered something new: the power of a blazer. He’d remarked, at the beginning of the afternoon, that he’s not much of a formal dresser. But for that exact reason, an unstructured blazer (no shoulder pads) made of jersey material paired beautifully with his new boat shoes, and a slim-fitting polo. (For more on the magic of an unstructured blazer, click here).

Finally, accessories from H&M: a sharp tie for Jake, a bowtie for Sam, some beaded bracelets, and we were done (yes, bowties have made it to the Bar Mitzvah circuit. For more on that, click here).

This slideshow requires JavaScript.


I was struck, working with Sam and Jake, how differently two twins could relate to style. Each had their own ideas of what worked for them and what didn’t, but each was eager to branch out, to stretch, and to try something new.

It seems to me that while becoming bar/bat mitzvah is very much about the responsibilities of adulthood, it is just as much a precious opportunity for young men and women to hit the “reset” switch on who they have been since early childhood, and to begin making new choices for themselves: to explore who they are and who they want to be.

And while much of this growth is invisible to the outside world, new, carefully chosen clothes can give him/her the chance to openly express and celebrate these newfound freedoms, choices, directions, and inspirations. Indeed, seeing Jake’s eyes light up as we put the finishing touches on his outfit – and seeing Sam catch his reflection in a men’s jacket and grown-up, stylish shoes – it reminded me why I feel so passionately about style.

Style was perplexing, to me, when I was 13. I felt as in the dark about what I wanted to wear to school each day as I did about what I wanted to be when I grew up. But I remember that day, when I saw my first pair of Chuck Taylors on my feet (orange, no less). I knew that I was ready to take my first steps into deciding for myself how I wanted to live my life.

Wearing those shoes made my outsides matched my insides. And isn’t that the definition of style?

This year, celebrating the 28th anniversary of my Bar-Mitzvah.

This year, celebrating the 28th anniversary of my Bar-Mitzvah.

Ready for your own Style-Up?

Live in the bay area? Email Style For Dorks.

Outside of the Bay Area? An On-line consultation will provide you with a handful of great items, some new looks, and a spring in your step. Email Style For Dorks.

Want to See More Style-Stories?

Seven Simple Steps to Bump Up Your Style-Game

This post follows my recent feature in Lifehacker’s “Ask an Expert” series. It serves as a deeper dive into some of the great questions that readers submitted.

An eye for style involves a zillion tiny calculations, many of which are subconscious. You have a “feeling” about what will work, and what won’t. But good news! Like every other skill set, when you’re new to it, you’re in a great place because the learning curve is steep! Even a small effort can net you big results.

You know that quote: the journey of a thousand steps? Yeah, you know the one.

Well, the journey of bumping up your style-game only takes about ten steps. And if you take one step a day, well, do the math.


“Thanks, Uncle Russ, for your vintage bowling shirt. Now, it’s going to live with someone who needs it more than my closet does.”

Step 1: Go through your closet and get rid of everything that is too big, too small, has a stain, or that you haven’t worn in 1 year.

Purging your closet is god for your psyche/soul/sub-conscious/feng-shui and whatever else. If you’re still holding on to Uncle Russ’s vintage bowling shirt, a lucky hoodie from the college days, or a pile of concert t-shirts with fond memories – and you never wear them but can’t bear to part with them – do what I do: put them in clothing limbo: a large cardboard box. In another year, if the absence of the garments does not have a deleterious effect on your life, donate the whole box to the Salvation Army.

Warning: do not look in the box, once it’s sealed. Maybe you’ve heard of Pandora?

2. Ask around for a hair stylist recommendation

Be prepared for sticker shock if you’re used to 10 dollar cuts. Trust me, it’s worth it. When you head out to pop some tags, you’ll know better what you like – and what you don’t – if your hair is on point.

If no one you know can hook you up with a proper rec, then go to Yelp, and trust that you get what you pay for. Aim for 50 bucks.

3. If you don’t own a pair of dark blue indigo jeans, get one.

Friends, I cannot overstate the power of dark indigo. Denim magic is only partially about fit. It is equally about color. And what white does for a masterpiece’s canvas, dark indigo does for your whole outfit. It looks awesome with anything, on anyone. And the good news is that decent, dark denim costs only 50 bucks.

Swap out that baggy, acid-wash, carpenter pair from 1997 and prepare for magic.

No other shoe is as versatile as Clarks Desert Boots.

No other shoe is as versatile as Clarks Desert Boots, which even suit a suit. So to speak.

4. Get a pair of Clark’s desert boots. Brown.

Generally, this blog is about teaching concepts and principles, and not pushing any particular brand.

But some brands set the style — and some styles, like dark denim, are so perfect, so flawless, they never fade.

Clark’s Original desert boot (which have a soft, whitish, rubbery sole, so cool but not essential – you can get away with Bushacre II) go with shorts. And jeans. And dress pants. Man, I wear them with suit.

Get your size by visiting a department store near you, then bag them on eBay for $65-75.5.

5. Get a white OXFORD or CHAMBRAY shirt in the smallest size you can fit into.

Most of the usual suspects carry Oxford Cloth Button Downs for $40-75. Just to be clear, this is not a white dress shirt. Oxford cloth is nubbier, more causal – sort of a hybrid work/office shirt. It looks great on everyone (including women). And it looks great with everything.

Likewise, Chambray (click here for a deeper dive) is not denim, though it looks a little like it. Pick one up on eBay, or at J.Crew, Banana Republic, Gap, or a local resale shop. 

knittie6. Get a knit tie from TieBar.com

You don’t wear ties? You do now. 

7. Finally, get either a blue or grey blazer… Or a thick, cuddly cardigan.

You don’t need to drop bank. A decent cardigan or blazer might run you fifty bucks. Be sure it is snug, and here’s a rule of thumb: even if it’s too tight to button, it’s a great layer piece. Do not, under any circumstances, buy a big, boxy, hanging blazer – no matter the brand.

You have completed your seven-step journey.

Prepare for complements.

before after

All seven steps, done as one. Sepia tone optional.

Want to see all seven steps, completed in an hour? Read the story here.

Style Story: Jerry – One Outfit to Rule Them All

Above, Jerry’s Style-Up: Before and After.

Meet Jerry — in his own words. The cartoons are mine.

1. Describe your style, in general.


Jerry rocking his usual steez – “Jewish Nerd Dad Chic.”

Is “Jewish Nerd Dad Chic” a thing? I wear lots of t-shirts with logos and/or imagery, usually design, software or pop culture-related. I also own a number of fine vintage silk shirts and florals. I rarely wear a suit and tie into business meetings, as I’m expected to represent the “creative” element — “business casual” shirts and pullover sweaters are de rigueur. Nice jeans or corduroys during the week, cargo shorts on the weekends. Also, a hat or head covering is typical — a knit skullcap for business, a driving cap otherwise.

2. Tell the story about why you decided to do a Style Up?

I don’t dislike my current day-to-day style, but as a busy father of three, I don’t frequently refresh or reconsider it — and I occasionally wait too long between refreshes. My business wear aesthetic could use a dash of sophistication. Then, I was peer-nominated for a very prestigious award at my company, wherein I was invited to an exclusive banquet with the CEO, CFO and other Senior Operations staff. I recently moved to Silicon Valley and had this one moment to make the best possible impression on the top brass. I wanted to project effortless refinement and a fashion forward sensibility without pretension or overstatement. My existing “dressy casual” lineup wasn’t particularly reflective of my personality.

3. What did you learn from the Style Up?

I learned that the Style business is all about relationships. As I watched Evan navigate the racks, I also watched his interaction with the floor staff at the various stores — the rapport, comfort and understanding that flowed between them smoothed the

So as not to leave anyone out, including all 4 natty members of OK Go.

So as not to leave anyone out, I’m including all four natty members of OK Go.

entire process, and I realized that getting the salespeople on your side is helpful to achieving the best results.

4. If you could channel the Style Traits of any personality, who would it be?

Either of the front men of OK Go — Damian Kulash or Tim Norwind. Those guys personify excellence and innovation across music, visual media, performance and conceptual art — all with rakish good looks and impeccable style.

The Style-Up

The Challenge

The photos Jerry showed me of last year’s award banquet attendees featured well-dressed men and women in suits and dresses. Because of the short turnaround, however, anything we bought had to fit off the rack. No tailoring or altering would be possible. This ruled out a suit, which could require multiple trips to a tailor.

Conclusion: we would use a 3 Step Plan to find a “non-suit suit.”

6 shoesThe Plan, Step 1: Shoes are the Foundation

When learning any skill set, people discover that a) what they thought was simple is actually complicated. Then, with time, learn that b) what is complicated can be made simple through a series of steps.

In Jerry’s case, we had a few hours to nail a single outfit. And we had access to the entire downtown San Francisco area, with dozens of stores. Too many options.

That’s why we started with the shoes. Not only does an outfit begin with your feet, but also, it would help Jerry and I articulate what kind of aesthetic suited him best for the occasion.

Jerry and I looked at six types of shoes at Nordstrom, each representing a different “style platform.” In each category, we pulled from the shelf only the best model; it needed to be eye-catching without being ostentatious.

Oxfords were “too plain,” and everything else was too casual for this critical evening; Jerry selected the brogues.

One watershed choice remained: Nordstrom sells a great line of brogues from Allen Edmonds in a few different colors. If Jerry chose brown, that would send us looking for an outfit featuring brown, blue, grey, and red: stylish but casual. If Jerry chose black, it might indicate that he was looking for a more restrained, formal look. Jerry’s final choice, however, was a bit of a style-swerve: Blue leather, red laces.

neumokAllen Edmonds hit on something amazing with this particular shoe, the Neumok. While the wingtip stitching affords it plenty of flair, the shoe’s basic style is such a classic, it can easily contain the eye-catching colors without suffering any loss of elegance. (For a deeper dive on achieving that balance, click here).

Now, we knew: we were going for a look with attitude.


Simply a placeholder for an even better outfit.

The Plan, Step 2: The Working Title

When I was a teenager, I was fascinated by the idea of a “working title.” The Beatles, for example, used “Badfinger Boogie” as a working title for a new piece which, eventually, they named “With a Little Help From My Friends.” It’s hard to imagine that such a familiar, classic, and, well, perfect song ever had a different name…or no name… but all great things go through iterations, and placeholders are needed to mark progress.

Same for Jerry’s outfit.

Since we were already in Nordstrom, we began to look through the racks to see what caught our eye. Only one shirt stood out from the endless racks of button-down shirts, and not surprisingly, it was gingham.

Gingham is an amazing pattern because it can be dressed up (I love wearing gingham with a suit) or it can be dressed down (jeans and canvas sneakers or Clark’s desert boots). Meanwhile, it “builds structure” — the vertical lines build height and the horizontal lines broaden shoulders and give the arms definition. We paired the gingham shirt with one of my favorite go-to ties: navy blue knit. Like gingham, a knit tie dresses up an outfit, and yet, it retains a casual edge. It stands out, subtly, from crowds of shiny silk ties.

On the other hand, the shirt wasn’t tailored as sharply as I wished, and the tie was a bit underwhelming in its quality. Don’t get me wrong, the outfit would have looked great in almost any workplace, and maybe even for Jerry’s award ceremony, but I felt like we could do better.


Notice the same gingham from above, but in a finer size, a more formal color, and paired with a killer blazer.

The Plan, Step 3: The Upgrade

From there, we headed to Club Monaco, a great Canadian label, featuring premium gear and excellent service. The store we visited was full of rugged but refined sweaters, chinos in rich, blue fabric, a handful of shirts featuring variations on classic themes, and blazers that catch the eye with their understated elegance. It was not cheap, but you could clearly see what your money was getting you.

One of these blazers caught our eye within a minute of walking in the door, and soon, we found a gingham shirt that picked up the general approach of our “working plan” above, but in a dark, charcoal hue, and featuring  a smaller print (generally, smaller prints are more formal than larger prints, even in the same category).

Lastly, a knit tie – like the tie from Nordstrom, but in a darker blue, and featuring pleasing, slightly irregular weave, a hallmark of handwoven cloth (vs.  too-perfect mass-produced).

This new ensemble, layering dark navy and charcoal, allowed us to assemble an outfit resplendent with texture. While other award attendees might wear an obscenely expensive Italian suit or eye-catching patterns or ostentatious detailing, Jerry’s new outfit was captivating in its subtlety.

It wasn’t trying very hard to be awesome. It WAS awesome.

champaigne v4

An unstructured blazer can be paired with a t-shirt for casual friday.

An unstructured blazer can be paired with a t-shirt for casual Friday.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting room door.

Live in the bay area? A Style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Email Me and we’ll get you on your way!

Outside of the Bay Area? An On-line consultation will provide you with a handful of great items, some new looks, and a spring in your step. Click to Email Me.

Want to See More Style-Stories?

Style for Dorks Podcast: San Francisco’s “Bitch Talk!”

Link to Podcast here! bitchtalk

Check out my podcast debut with Erin Lim, Karyn Paige and the sassy San Francisco podcast, Bitch Talk Podcast. Within, the power of good shoes, how and when to break style-rules, the neologism “Nircited,” and the question: is your personal style broadcasting what you want it to?


Link to Podcast here!

Cufflinks: How To Wear Them…And How Not To.

Recently, I had the pleasure of answering the following question, sent by an audience member to Dear Veronica – Veronica Belmont’s show on Engadget. I welcome my readers to watch the original video clip here (and embedded at the end).

“I’ve got a stash of Most Excellent cufflinks… I’d love some guidelines on when and where I can get away with rockin’ the French Cuffs.

Once upon a time, the only thing I knew about French Cuffs is what I learned from Mel Brooks’ “History of the World: Part I.”

Fortunately, since then, I have developed a more nuanced understanding.


Sadly, the cuffs are all that survives today from these stylish gents.

But first, a little background:

French cuffs burst onto the sartorial scene in a “life-imitates-art sort of way” when Alexander Dumas published The Three Musketeers in 1844. Pretty soon, every man in Europe was wearing his cuffs rolled back and fastened with a couple of decorative baubles.

To this day, while we credit the French with their eponymous cuffs, the French called them poignet Mousquetaire — Musketeer Wrists.

Wow. Who knew.

For the next hundred years, true gents rocked French Cuffs. This culminated with personalities like Sean Connery and Frank Sinatra who brought the look to cinema, fusing stardom and style into a well-dressed masculine ideal. This set the standard for the next generation.

 French Cuffs Today: 

office spaceUnfortunately for the French Cuff enthusiasts of the world, in the 80s and 90s, many men began to idealize high-powered Wall Street executive types. The Wall Street Boss look was bad enough, but scores of imitators created a Bill Lumbergh archetype – middle managers with bad taste and chips on their shoulders. They wore cufflinks, contrast collars, suspenders, lurked around cubicle corners with their power-lingo, and pretty much ruined the French Cuff for everyone else.

The Return of the French Cuff:

The last ten years have seen a sartorial revival: ties and jackets have returned to the workplace and the pub, but slimmer, now, combining the formality of menswear with a youthful silhouette. Cufflinks, on the other hand, remain a throw-back accessory, mainly appearing at weddings and in the occasional boardroom. As a result, if you’re under the age of 50 and/or you are not a bank president, cufflinks can easily throw your look off-balance.

This doesn’t mean you cannot wear them, it just means you need to be aware of an important concept: “Flair-Up.”

flair chartFlair-Up:

The movie Office Space (1999) features a hilarious and absurd restaurant wherein employees are given kudos for featuring “flair” on their uniforms (and are reprimanded for any lack thereof). “Flair” refers to buttons, pins, badges – you know. Wearable tchotchkes.

In real-life style, I advise people to think about “flair” as an essential component of style – it’s what transforms a suit and tie (or Tshirt and jeans) from into a fantastic outfit.

Certain colors, patterns, materials, accessories – all these add +1 to your flair… until you hit +4, at which point it’s a “flare up.” The outfit incinerates into an ongepotchket mess.

Click here for a deeper dive on flair and the dreaded flare-up.

Cufflinks, to put it simply, burn through all your allotted flair points. That means: if you want to wear them, tone everything else waaaaay down.

Step 1: Start with the cufflinks.

If you’re new with cufflinks, it’s easier to build an outfit around the links you’d like to wear than to put an outfit together and hope you have a pair of links that match.

4 tiesStep 2: Select a tie

If you’re going to wear a tie, choose one with complementary colors.

headon banker

Look 1. Classy-Styley 

Pair well-made, understated cufflinks with your tie – in this case, tiger eye cufflinks with a tie featuring brown accents. The white shirt and grey jacket keeps everything else in check. Stick to strong, neutral colors: black, grey, brown, blue.

Look 2: Designy-Styley

To avoid looking like a stock-broker or a bar-mitzvah boy, lose the tie. Go ultra modern. Pair some minimalist cufflinks (like these grey or red cufflinks from BLOCK) with a neutral blazer and some slim chinos or slim, dark jeans. If you want to step up the flair, wear colored pants to matching the cufflinks (red or blue) but keep the shirt neutral and avoid any other loud accessories.

red linksup close block

Do’s and Don’ts

  • Do stick to clean lines, simple colors, and simple construction.
  • Do match your cufflink color to another color you’re wearing – and match the level of formality to the rest of your outfit. ie Colored acrylic goes with colored chinos. Silver and semi-precious stone goes with dress pants and a blazer.
  • Do match your cufflinks to a thin tie – 2.5 inches or narrower. Wider than that and Bill Lumbergh is going to ask you to “go ahead and come in on Saturday.”
  • Make sure the rest of your outfit is on point. If your pants, shirt, or shoes are not well fit and well assembled, the cufflinks will actually accentuate the problem.
  • Don’t wear (or give as gifts, for that matter) novelty cufflinks with people’s initials, funny sayings, or tiny metal monopoly-pieces representing your careerhobby, or ironic nerd-passion.
  • Avoid cufflinks featuring salvaged material: steam punk cufflinks, circuit board cufflinks, typewriter key cufflinks, or anything that, enlarged, would be a desk-toy. All of these are conversation pieces, and you should not be having any conversations about your cufflinks. Keep them understated.
  • Avoid large gold and silver cufflinks which say “mafia boss.” Leave this look to the pros. And leave them alone, while you’re at it.
  • Avoid pairing cufflinks with blingy gold or silver watches or jewelry. If you’re wearing cufflinks, that’s both your flair and your jewelry quota right there.

14 DAYS OF REFLECTION: EPISODE 12 – Context, Context, Context

Why I haven't posted in a month had something to do with my cultural context.

Why I haven’t posted in a month had something to do with my cultural context.

Q: Why have I not written anything for the last month?

A: Long answer. It begins with G.I. Joe.

When I was 14, I rounded up all my action figures, put them into shoe boxes, and hung posters: Lamborghinis, girls in bikinis, and a couple of rock bands.

I know. Super original.

If you had told me, six months earlier, that my beloved G.I. Joe space station would soon be as irrelevant to my life as a Fisher Price barnyard, I’d have said, in the parlance of the day, “bite me.”

And yet, that’s exactly what happened. One spring day, with very little fanfare, I hid the space station, the stealth fighter, and even the awesome Terrordrome under the bed, in the back of the closet, and behind the extra sofa in the attic. (Where they are to this very day).

In my life, I have gone through many phases and fads. I have been, at various times, obsessed with (in no particular order): electric guitar, capoeira, the Best American Short-Fiction series, Indian New-Age kitsch, salsa dance, Chinese tea, Bioshock, Dungeons and Dragons, vintage tube-amp stereo systems, and comic books. With each of these, I threw myself in, feeling a burning passion to understand, learn, do, master. Then, at some point, it no longer seemed relevant, and I put it away.


A prime sample of Jerusalem’s Fashion Glitteratti.

This summer, I spent three weeks in Jerusalem. Say what you like about the magic and the power and the history of the city, it’s one of the least stylish places imaginable. An image search for “Srugim” (an Israeli TV show, similar to “Friends,” but depicting life in the hub of  Jerusalem’s religious-singles’ scene) can confirm that everyone looks sort of shlumpy.

I’d packed my suitcase with some red, summer chinos, a couple of skinny bow-ties, a light-weight blazer, some Fred Perry polo shirts — all the stuff I wear when I want to look dapper on vacation. But most of it sat, unworn, in my suitcase. Instead, I wore the same three T-shirts, over and over, washing them in my hotel sink. On Shabbat, I wore a white dress shirt.

In the span of three days, I’d lost interest in anything having to do with clothes. And as someone who has been passionate about style for years, I have to admit – I was a little concerned. Would I return home in droopy khakis and billowy, white dress shirts? Would StyleForDorks.com go the way of the G.I. Joe Mobile Command Center?

My main source of inspiration.

My main source of inspiration.

As it turns out, once home, many things returned to normal. I was reunited with my main source of inspiration, and I dove headfirst into a pile of cardigan sweaters, gleeful both for the variety and also for the Bay Area weather, permitting my stylish layering.

Some might credit my fashion-fluctuation with Jerusalem’s inherent spirituality obliterating my interest in all things vain.

I, however, believe it’s about context.

There is nothing very funny about a pirate, per se. But a pirate on an escalator? The misalignment in context makes for a comic spectacle.

Likewise, amidst swimming-suited beachgoers… look at that man in a tuxedo! Awkward and absurd! Let’s go shove him into a sand castle! 


A seersucker suit belongs in Jerusalem like a pirate belongs on an escalator.

Style is about dressing for the place and the time. In summer, bright colors. Linen. Stylistic nods to Nantucket, Hawaii, Cuba, Southern California, the Mediterranean. In Winter, wool and tweed, sweaters, muted tones, and stylistic nods to the Ivy-League campus, to ski slopes, to the Holidays.

In winter, I lose interest in my summer outfits, and in summer, I lose interest in my winter gear. And in Jerusalem, I focused on other things: teaching. Food. My memories. And my outfits fit that context. Everything was easy to wear, easy to wash, and easy to shove into a suitcase.

Preparing for to shop in Jerusalem's ultra-orthodox neighborhood, Meah Sha'arim. Wearing ritual fringes for Kosher-Steez credit.

Preparing to shop in Jerusalem’s ultra-orthodox neighborhood, Meah Sha’arim. Wearing ritual fringes for Kosher-Steez credit.

On the other hand, not ironically, cloth and clothes did play a major role for me in Jerusalem.

Future posts will explore how (and why) I spent an impressive amount of time tracking down a wool prayer shawl (tallis) and a white, linen robe (kittel) with a fervor I normally reserve for a Black Fleece suit. I agonized over white kind of white Kippah to purchase for a very significant event next summer. I even wore fringes to blend into the cultural milieux of an ultra-orthodox neighborhood. In other words, I didn’t lose interest in style. But style manifested in other ways.

It was, and is, an expression of who and where I am. The constant is that style is about the Self in context.

Even if that Self moves forward from time to time.