men’sstyle

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.

bowling

“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.

14 Days of Reflection: Weekend Look #3 – The First Day of Vacation

IMG_4440For many people, and understandably so, the second that vacation begins, the care to construct a styley look ends. And truly, I will never fault anyone for taking off the work clothes and slipping on the t-shirt, shorts and flips-flops.

On the other hand, as long as you gotta wear something (assuming you’re vacationing with family in, say, San Diego, and not at “Sea Mountain Nude Hotsprings”) why not wear something well put together?

The trick is this: if you know that you won’t have the headspace to pick out a bunch of vacation outfits as you rush to cram your suitcases, pick them out in advance. Way in advance. In other words, identify a couple of pairs of pants, a few shirts, a pair of shoes, and yes, a classy layer-piece: a sweater or an unconstrcuted blazer or both.

Then, when your plane takes off in three hours and you still haven’t filled your suitcase, you need not panic: you know what you’re packing.


As Gabi and I approach our first week as (and with) future-family, I’m struck by two competing forces at work. First, there is, well, the familiar. Gabi’s family is very tightly knit and meals with them are full of laughter, good-natured ribbing, and decades’ worth of stories. They seem to appreciate and understand my humor, although folks are divided on whether my puns are brilliant or groan-worthy.

IMG_4437On the other hand, there is the unfamiliar. Deeply unfamiliar. People who are dear to me, and have been for years, take on roles of new significance. Future father-in-law. Future mother-in-law. Future brother-in-law. I have never really known these roles in my life, and I’m acutely aware of this, the way a new article of clothing feels very there.

It seems appropriate, in these circumstances, to wear something fitting this odd and beautiful confluence of well-known and never known. Here, on this San Diego beach, what could do that better than comfy sneakers, a soft sweater, my old hat – and a red flower in my lapel?

Blogging Back and Forth Forever: Getting Engaged, and 14 Days of Reflection

 For those in the know, “Blogging back and forth forever” ))<>(( can be a our little inside joke, a little indie-film triviata.

For those not in the know, just take my word for it; It’s weird and sweet and evocative and sort of grody and, well, forever.

Sort of like life.


Yesterday, Gabi and I got engaged. She looked beautiful. I was wearing a fantastic suit. There was a lot of crying and laughing and a guest appearance by local San Francisco celebrity weather pattern, Karl The Fog. 

This engagement was a long time coming. Gabi and I built our bridge towards each other step by step, over a span (no pun intended) of three years. When it was time to take the plunge (eek, definitely no pun intended) it was with eyes wide open — taking in the dazzling sun on the San Francisco Bay (metaphorical for life’s various gifts and treasures) as well as the mirk, the clouds, the unknown. We planned it together, down to the exact day, the exact time of day, but for Gabi, the details were unknown. Sometimes, you need to keep some mystery – to recreate, in my opinion, the true Mystery that we are all faced with: our Existence. Part of it are revealed, from time to time, like the majestic Marin tower of the Golden Gate bridge.

It emerged, as we drove across the bay, as if to guide us on our paths towards eternity.

 Today I am 41. Dear readers, you may have figured out (“Surprise!”) that this project, “14 days of reflection,” was intended to crescendo with my innocent little question to her, but with that now residing nearby as a memory, it’s time for me to celebrate my birthday. Gabi has given me many gifts over the past three years, and while the greatest one, by far, is the gift of our life together, today, we laughed about the way that she guided my path as I crafted my on-line persona (more on the deep power of the persona, here). My fashion style was in place, already, but my communication style is very much a joint project, and I suspect it will be a project that will involve a lot of creativity and a lot of time.

May this be a year of thriving.

May this be a year of growing close together.

And may this be a lifetime of exploration for my fiancee and I, both in person, but also online.

May we blog back and forth forever.

14 Days of Reflection: Episode 4 – What Goes Around Comes Around, One Level Higher

meandhavnehSitting in my desk chair, a voice called my name and I turned and froze: a former student had showed up for our run. A run I’d completely forgotten about.  He was dressed in tank-top, shorts and running shoes.

Ten minutes later, I was wearing an outfit cobbled together from the lost-and-found: a sweatshirt two sizes too small, running shorts, and a baseball cap with the school’s logo.

On that run, we talked about the same thing we used to talk about when he was my student and I was his teacher: reaching your goals, overcoming fear, being true to yourself. And it was the same running route, too: Scott Street. Presidio. Marina. The hill.

That hill, stretching from the bay to the Pacific Heights, 3 excruciating blocks, used to be a major topic of conversation on our runs. It was the central symbol in our talks about life.

“Keep your eyes on what you’re doing now. Don’t get discouraged by how far away the goal may seem. Promise that you will only climb for the count of 10. When you’re done, recommit to another 10. True victory comes when you’re no longer counting.”

Here we were, two years later, and each of us had grown so much, the same running loop, the same scenery, the same running loop.

Maybe a level higher, maybe a level deeper.


Seersucker Phase 1

Seersucker Phase 1: 7 Years Ago

Moving topics, from the Fillmore Street hill to Capitol Hill:

In less than 24 hours, Washington DC will honor Seersucker Thursday.

Former Mississippi Senator Trent Lott inaugurated this day in the 1990s to revive this storied fabric. Once, it was the only thing a Senator could wear on a pre-air conditioned, muggy June day.

In my closet, I have three seersucker jackets.

The first is from Urban Outiftters, and I bought it seven years ago, with the remainder of a gift certificate. It’s essentially an unstructured blazer, without the actual pucker that seersucker is known for. (Incidentally, the word Seersucker means milk-and-sugar in Persian, referring to the color of the stripes)

The second two are from Brooks Brothers, and I bought them two years apart.

Seersucker Phase 2 departs from the norm, in that the pattern is the same, but the jacket and trousers are actually a different color.

Phase 2

Seersucker Phase 2 : Three Y ears Ago

I had to get used to Phase 1 to do Phase 2.

Then came along Phase 3. The stripes in the jacket are a different width from the pants, and since Gabi and I were at a festive (and blazing hot) outdoor wedding, I went gangbusters and yanked a parasol from a parasol-pile to keep us in the shade. And to add to the outfit-awesome.

Seersucker: Phase 3

Seersucker Phase 3: One Year Ago

Seersucker never went away, but I moved on.

Old rules, like “Don’t match your tie and jacket” and “you can’t wear seersucker after Labor Day” went out the door. (For a list of Trent Lott’s other Seersucker taboos I also advise ignoring, click here).

I was finding my own voice, and pushing the rules as far as I cared to.

Here, on the cusp of my 41st birthday, many of the challenges in my life (most of them in my head) are no different than the challenges I faced when I was 31. But I’m better able to handle them. I can climb a much bigger hill.

Same hill. Same material. Same style. Different me.

One level deeper. One level higher.

leanonscope

Vintage Varsity: Lettering in Style

letterman

Before David Letterman, there was THE Letterman.

My own history with varsity style involves a lot of very un-varsity moments.

I would eventually experience great disappointment in discovering that the only part of this movie that applied to my freshman year at college was the nerdiness.

I would eventually experience great disappointment in discovering that the only part of this movie that applied to my freshman year at college was the nerdiness.

First, when I was a little kid, there was varsity-superhero Letter Man, a favorite regular on the PBS show, Electric Company. His sport: ripping the letter from his sweater and applying it to spoiled words – thus restoring “custard” to those who’d been forced to eat mustard. Kids learned to read. The word/world was saved.

Then there was “Lambda Lambda Lambda,” the fraternity in which a gaggle of outsiders found comradery, legitimacy and pride in Revenge of the Nerds.

Moving on, there was my big opportunity to earn a letter in high school. No, not in football. In the National Speech and Debate Organization. I would go on to win second place in state, but stupidly, I turned down the letter.

That move would go on to haunt me for decades.


varsityusageThe unfortunate mistake I made had nothing to do with the prestige of lettering, seeing as how my award-winning speech about drawing Beatles caricatures afforded me all the prestige I needed. Rather, I lost the opportunity to bag one of those cool sweaters.

Until this year.

The usage infographic on the right testifies to the return of the term “varsity,” in modern parlance. This is especially fortuitous because it coincides with the availability of varsity apparel for style-dorks. The monopoly on this classic piece of Americana, previously held by the sinister jocks (Alpha Betas and their cronies), has been broken.


vintagevarsityBefore I tell you where to nab a great varsity sweater and what to wear it with, a little history. First, the word varsity is derived from the word “university,” and simply reflects an outdated pronunciation. The tradition of the letter goes back to the second half of the 1800s, when Harvard used them to mark uniforms, and would award the lettered jersey to the captain of a successful team at the end of the season.

Ten years before this, a successful British military commander during the Crimean war made popular a button-up woven garment. His name?  James Brudenell, 7th Earl of Cardigan.

These historical events, combined with the roaring twenties and the rise of college culture, lead to the proliferation of the varsity sweater across America, and that leads us to today, where I have a few to many of them in my closet, and yet, weirdly, not enough.


kippersweater

Americana Overdrive

How to rock a varsity sweater

While you could wear a varsity sweater as a layer piece over whatever you wanted, I’d like to suggest that the fun multiplies with additional vintage style elements – many of which are as common as a pair of dark, indigo jeans, with a generous cuff, and even a bow-tie or newsboy cap. 

On the other hand, if you’re concerned about looking too costumey, have a peek at my How Much Flair infographic, which will guide you in upping your style-game without going overboard.


Look 1: Americana Overdrive

This look (above) pairs a great varsity sweater by the progressive clothing company Kipper Clothiers with a denim tie and a gingham shirt: Americana layered on Americana. This sweater is beautifully made, soft, and stylish. Grab a pair of incredibly cheap, but incredibly styley PF Flyers to complete the look.

Note: if you want to layer this many patterns, stick to a tried-and-true color palette: red, white and blue.


greensweaterandplaidvintagevarsityLook 2: Two Layers of Vintage

norristhrash

Stay Fly Thrash: Advanced Style Swerves

This sweater lacks the typical letter of a varsity cardigan but hey, notice the stripe on the sleeve? That’s Thom Browne’s nod to the varsity stripes – which, incidentally, stand for how many years you participated in the sport. In this case, the sport of styliness. On the left, the sweater is paired with a gingham shirt, an idea I shamelessly ripped off from StayFlyThrash, who pulls off advanced style swerves that require a PhD in cool. Somehow, the strong colors work, and pull the look off the college campus and push it into post-modern fashion-zone.

On the right, paired with Chuck Taylors, plaid pants and a bow-tie,  I’m ready for a Gatsby party. (On the rare occasion when there isn’t such an event happening in San Francisco, one is happening in my head).


leanonscopeE-bay Pullover

This sweater came from eBay, and it’s a success story in the power of the saved search.

I’m a big fan of Andre 3000s now defunct label, Benjamin Bixby (wherein he combined his middle and last name with vintage prep style).

This sweater probably retailed for the cost of a semester at an ivy-league college, but I paid very little for it.

On eBay, you can ask for an alert if a particular item is posted. 6 months ago, I saved a search for Andre 3000’s finest, received a notification a few weeks ago, and put in a low, low bid.

Here, I pair it with the ubiquitous dark denim, a used newsboy Goorin Brothers cap,  and some PF Flyers, for an old school look. By the way, the whole outfit cost me under $80. Take that, Yale. I learned my economics on the internet.


ragnbonewsuit

fullonsuitSuitable for Anywhere

Here are two ways to pair vintage varsity with a suit. On the left, a vintage tweed suit pairs beautifully with the Kipper Clothiers cardigan.

My advice: make sure the colors compliment each other, and avoid too smooth a suit; you want something with texture to balance the cozy sweater.

On the right, the varsity look lives only in the sleeve of this dress shirt from Gant. I waited until this shirt was languishing on the clearance rack and got it for a third of the price.

Incidentally, buttoning the top button (otherwise known as an “air tie“) helps to keep the look streamlined and casual – even while earning As for awesome.


gabiinstylgram

Letters for the Women’s Team

In case it wasn’t clear how much I love the vintage varsity look, maybe this will convince you, and maybe it will give you some ideas of your own: I poked around online and found a bunch of Rugby by Ralph Lauren cardigans for someone special.

Gabi (said special person) wears a lot of great dresses, often with strong, primary colors. I wondered: how would those dresses pair with a vintage-style varsity sweater? Answer: amazing.

The Rugby label is now defunct, but that doesn’t mean it isn’t available. Head over to your favorite online auction and offer a bid and see if you can’t bag a once-super-expensive sweater for much less.

The sweater lends the outfit a cuddly, sporty aesthetic, and she pairs it beautifully with some Chuck Taylors, Clark’s Boots, or a pair of vintage heels.


troublephoto

Sweater by Ralph Lauren Rugby, socks by Happy Socks, and hat by Goorin Brothers. Pair with a wool tie and a collared shirt and wear it anywhere.

Dress Up, Dress Down

In an earlier post of Dress-Up/Dress-Down mashups, I got pretty nerdy on the subject of mixing formal and informal elements, creating great art, architecture, and style.

Whether you decide to hunt for a varsity cardigan or not, I hope this post gives you some ideas for adding together sporty and dressy elements.

GQ can keep their $400 “sportscore” designer sweatpants. I’d rather pull my influences from a style that never goes out of style.

pinkybird3

Pinky Lee, Pee-Wee Herman and Thom Browne

pinkypeekingIf you’re under the age of 60, you probably don’t know the name Pinky Lee, but trust me, you know who he is.

Today, if a man wears a suit and the sleeves end inches from the wrist, if the pants reveal three inches of shin – if he wears a bow tie and clunky shoes – he’s a disciple of designer Thom Browne. The cropped suit, the checkers, the bow-ties: the look has swept the fashion world from haute couture to suburban mall to First Lady Michelle Obama.

30 years ago, if a man wore a suit and the sleeves end inches from the wrist, if the pants revealed three inches of shin – if he wore a bow tie and clunky, white shoes – he was Pee Wee Herman. He won an Emmy for his show, Pee Wee’s Playhouse, which was ahead of the curve: gender bending, racially diverse characters taught children (and adults) good lessons without being preachy.

60 years ago, all of these exact elements appeared on-stage in the form of the Pinky-Lee Show, helping pave the way for children’s programming.

One additional crucial element binds three generations and two industries together: the shrunken suit. Pinky didn’t invent it, but maybe he made it famous.


pinkysuitPinky Lee was children’s TV before there was such a thing as children’s TV. Contemporaneous with the Howdy Doody show, The Pinky Lee Show was more spastic, had a lower production value, and lacked the clever marionettes of Howdy-Doody. But The Pinky Lee Show had something Howdy Doody never had: Pinky Lee himself.

Born Pincus Leff in 1907, Pinky Lee became a master of slapstick in the 30s and 40s, borrowing from Burlesque comedy foms – and by “Burlesque,” I refer to the genre of variety show that arose out of Victorian cabarets and clubs: jokes, dance, baudiness, mock irritation at various annoyances, pratfalls, the works. It’s the grandmother of modern comedy and show-biz dance. I’ve watched some, including Pinky Lee’s early performances, and while it isn’t necessarily “LOL” by today’s standards, it’s kind of mesmerizing. That man can dance.

goatAfter a first attempt at a TV comedy series was cancelled, Pinky Lee started a children’s show: there, he pranced around in a shrunken-suit, directing his nasal lisp to the camera:

Come on, everybody – hug each other!

He sings and dances and plays xylophone, little dogs walk on tight-ropes, odd characters join him on a “playground” stage – it’s Burlesque stripped of the sexuality, cleaned up for an innocent audience, and it’s like watching Pee Wee’s Playhouse thirty years before it dropped. Pinky Lee’s “man-child” persona, the androgyny, the lisp, the tone of the show, it’s all there. And what else?

The one thing they all have in common: Short sleeves, short pants, loud colors: the suit.


Thom Browne, Pee Wee Herman and Pinky Lee: what a weird trifecta.

On May 2 is Pinky Lee’s Birthday, and in honor of that, here are 5 things we can learn from the Pinky-Lee and his later “incarnations.”


goggles1. Serious and silly are not polar opposites.

A google search for “Thom Browne” could cause any skeptic to blurt: he can’t be serious.

Behemoth vintage-varsity football players in Grandma-On-Easter colors. Nantucket-meets-aviator-schoolgirl. Androgynous phylactery sci-fi Chassidic.

It’s silly until you look at it, closer. Again. It’s silly and serious. Male and female, weak and strong, future and past, high and low, and every human proportion possible – all these are mashed up, turned on their heads. He turns the fashion runway into a playground, into Alice down the rabbit-hole: curiouser and curiouser.

varsitygrandmaAnd then, there are moments of true elegance. Genius.

All three challenge the audience: when am I serious, and when am I silly?

2. Sometimes, you find your calling after (or even through) setback.

Pinky Lee began his career following a set-back – during a time when Televsion was still forming as a medium, he appeared on a series of show with limited success, and certainly, very little critical success. Said the New York times about one of his projects: “Pinky Lee suffers from a dearth of both material and versatility.”

Thom Browne design: serious or silly?

Thom Browne design: Serious or silly?

Pinky Lee Design: Seriously Silly

Pinky Lee design: Seriously silly.

After his adult show was cut, a TV producer’s children missed him in their lives, and demanded he brought back.

A few years later, he was one of the biggest acts in Children’s TV, and had helped to establish the role of energetic host.

Paul Reuben’s came up with the idea of a children’s show following the disheartening loss of a role on SNL to Gilbert Gottfried.

Long live perfect failures.

thombrownegq

Thom Browne, himself.

Pee Wee Herman, himself

Pee Wee Herman, himself

3. Often, clean lines are best

Pee-Wee comes off as a man-child, but his show (especially early on) was full of adult innuendo (though most of it pretty juvenile in nature). Likewise, some of Pinky Lee’s work (especially in the 70s) is raunchy, and by todays’ standards, offensive.

That said, Pinky Lee once responded to a criticism: “I was the cleanest comedian in burlesque… No violence. There are no gestures, alluding to the derriere or other parts of the anatomy. Words like ‘lousy’ or ‘stinker’ are absolutely verboten… It’s a happy, wholesome show.”

And I have to say, the times I smile, watching Pinky Lee on stage, are when I’m moved by how uncynical, unprocessed, and clean it is.

Styles of excess come and go, but honest and clean is forever.

peeweeleaningpinkyears4. Whatever your passion, do it fully

Newsweek magazine wrote in 1954: “In his show [Pinky Lee] expends more energy than anyone this side of Jerry Lewis.”

Time magazine called him, “One of the hardest working men in TV.”

Indeed, watching him can be exhausting. Sadly, and on that note, his years of greatest success came to an end when he collapsed on-stage. It appeared that he’d danced himself into a heart-attack, though he was later said to have suffered from an acute sinus-infection.

pinkybird3While I never wish anyone to have a breakdown from doing the thing they love, Pinky Lee inspires us to put our fullest selves into our passions:

“I just want to do the thing I love the best – entertain children.”

5. Everyone needs to play

When I first began working in an office-environment, I was captivated by the clothing; I transitioned from the “whatever” of college sweatshirts and jeans to oxford shirts, leather shoes and a tie.

By the time I’d been working for a decade, dress clothes had become de rigeur. Putting on professional garb had become a restriction, rather than a thrilling form of make-believe, wherein I was a kid, duping everyone into thinking I was an adult.

measpeewee

Portrait of the Author as a Thom Browne / Pee-Wee Herman / Thom Browne disciple

When I stumbled across Thom Browne (literally ran past – as in, I was jogging past a store where a friend was picking something up), I was shaken, inspired by the idea that clothes could be elegant, powerful, classic, and clean — and also totally fantastic. An outfit could be gentlemanly and boyish at the same time. The timing was good; I had already begun to play with style, and with the roles that nostalgia and Americana (both forms of fantasy) could play in my own appearance.

I find it fitting that my style icon is sometimes made fun off by derogatory comparisons to someone shameless, hilarious, and in some ways, timeless. The irony – the insult is a compliment.

“I know you are but what am I?”

pinkyleehat

Happy birthday, Pinky Lee

Hats (small and checkered) off to you, Pinky Lee, not only for what you did, but also, for who you inspired.


3heros

blazers

How and When to Roll Up Jacket Sleeves

blazersNo, you won’t look like Don Johnson.

Yes, you can roll up your blazer sleeves.

Just follow these three simple rules.

1. Shoulders

NO: Big shoulder pads.

YES: “Unstructured,” casual jacket.

2. Material

NO: Wool, tweed, “suit material” – essentially, a suit jacket.

YES: Casual materials like cotton, jersey (sweatshirt material), or “sweatery” material.

3. Fit

NO: Boxy, drapey fits.

YES: Slim fit.

Got that? Put it on with a casual, knit tie, and roll ’em up!


Wanna know more about unstructured blazers? Check out my other posts on how, when and why to wear unstructured blazers.