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.


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.

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!

14 Days of Reflection: Episode 11 – “The Once and Future Ring.”


Photo feels like it was taken somewhere between 5 and about a million years ago.

Today, I spent two hours learning about my “Once and Future Ring.”

Once: it was silver. I bought it at a time of major transition, and truly, not an easy time.

On the outside, it was a period of major creativity. I was beginning to trust my eye, started to move beyond the biz-casual look I’d always favored, and I was featured in a style blog for the first time. I also, unfortunately, rocked a goatee.

On the inside: turmoil. I was single for the first time in years, experiencing a lot of work-related stress, and working through a lot of difficult emotions.

To top it off, I’d just lost a very special, older ring while trying to lift a neighbor’s fallen motorcycle. I put it in my pocket so it wouldn’t get damaged, and never saw it again. I needed something to fill the gap (or the knuckle, I guess).

Along came the ring (of the Once and Future variety): not from some wrinkled antiquarian peddling Mogwai and ancient artifacts out of a curio shop down a dark alley, but rather, simply, eBay.

ringhugeWhen Gabi and I were preparing to get engaged, we talked about rings.

She was ready with a ring: Gabi’s grandmother had left her own ring in Gabi’s mother’s hands (so to speak), and Gabi warmly anticipated wearing it proudly, and fondly, and was moved to tears just to imagine it.

Should I, too, wear an engagement ring? Yes. But I already wore a ring – one which symbolized so much. Without looking like a certain Beatle, it wouldn’t be possible to wear a wedding band, my old ring, and an engagement ring. Should I say goodbye to my old ring?

We looked online and found other vintage men’s rings. Some were very expensive and some were not, and honestly, none were as beautiful as what I already wore.


The ocean mirrors my ring? The ring mirrors my stone?

When Gabi and I were celebrating our engagement, through the window of our vacation house, we gazed at the water and the rocks of the Pacific; the oceanscape seemed to mirror the picture agate of my ring. The past and the future seemed to merge.

All at once it became clear; the stone would move forward with me (and us) into time. The metal ring, well loved through the years and losing its gold plating, would be laid to rest but reborn – recast in a metal that has been precious to me since youth.

Since I was young, I was shown my own Grandfather’s watch, made from a metal so soft and lively, it is  described by the name of a flower: rose gold. 

Watching a young man painstakingly trace the lines of my old ring on a computer screen, preparing a 3d printer to cast a wax mold, to design an object with a history as old as civilization itself, it seemed so fitting.

The old and the new combined. My life as a full-fledged human will so join that of another full-fledged human. The sorrow of the past is reworked into the joy of the future. And this artifact from my life will both pass into memory and forever join me in the years to come.

It has a good ring to it.

For the previous 10 episodes of Turning 41: 14 days of Reflection, click here.

14 Days of Reflection: Episode 10 – Bold Patterns to Filter Out Noise


The power of this shirt’s pattern comes from the fact that it’s simple, leaves plenty of space, and uses colors so classic, we made a holiday to celebrate the flag that flies them. (Picture taken June 14, Flag Day)

Listen to the sounds around you.

A gadget beeps. A refrigerator hums. Water gurgles through pipes through the ceiling overhead.

Rarely, in our world, is it actually quiet. We block these sounds out. Or do we?

Today, I listened to This American Life episode about a guy, working in an office, who went through the trouble of determining the musical key of the buzzing around him: fluorescent lights, monitors, dial tones. Sometimes, he said, the tones might produce a kind of invisible music. If we are lucky, he suggested, it might be a major third. A cheerful tone. If we are unlucky, it might be a minor tone, or worse, a tri-tone – a musical interval so vile that medieval music theorists called it the devil’s tone. The idea here is that people are influenced, emotionally by music. We all know that. So how could we sit in an office, listening to a minor chord or tri-tone, for hours on end, without negative implications? And vice versa – could the sound of the microwave, defrosting our morning bagel, harmonize with the freezer itself, forming an optimistic musical harbinger of the day to come?

The attention to detail struck me at once as whimsical and also profound. The noise around us takes energy to block out, to focus on, and as Jack Hitt suggests, never in the history of humankind have there been so many droning noises filling our ears. Gadgets and machines and motors in constant cacophony.

Indeed, I can’t stand sitting in a cafe near a noisy refrigerator, and conversely, I’ll note to myself, upon shutting off a heater or air-conditioner: finally, I can think!


This is the pattern (because of its simplicity and boldness) that a million lesser patterns are jealous of.

This is why we like to take quiet getaways to quiet places (although many of us have yet to take the final step of shutting down our devices once we’re there). This also underscores the value of the tradition of shutting off my phone and computer on Shabbat (a custom I should probably practice more thoroughly).

And this, perhaps, explains my love of certain patterns in clothing: notably – checkers and stripes.

In a world of chaos and constant noise, filtering down to simplicity can actually refresh and rejuvenate – on the inside but also on the outside. Sure, stripes can be bold. But also, there is purity to the design and it blocks out other noise.


You don’t need to wear stripes everywhere you can. But you could.

Five Rules For Selecting a Power Pattern

1. Try choosing a pattern in the simplest colors the eye knows: red and blue. Black and white.

2. Pair it against something neutral. Jeans or grey.

3. For a bolder effect, wider stripes. For subtlety, go narrow.

4. To increase noise, add stripes, but be sure you know how much flair you can handle (perhaps by peeking at this guide, first). 

5. Prepare for compliments.

For Days 1-9 of 14 Days of Reflection, Click here.

14 Days of Reflection: Episode 7 – Back to Life, Back to Reality


An interpretive self-portrait. “Blue Marble” photo courtesy of NASA, 1972.

I returned to work from a surreal, blissful weekend with a cold.

My nose burns, my bones ache.

Truth is, there’s something grounding or reassuring about the reality: mucous and all. In between the hugs and back-slapping, the retelling of the play-by-play, the flicking through photos, in between was DayQuil. Sneezing. My coworkers. Meetings. Phone calls and emails that had nothing to do with getting engaged, the meaning of existence, or love.

And this is good! This means that what happened last weekend wasn’t a dream (some day, incidentally, I’ll tell you about my dream, the first night of Gabi and my getaway, wherein a family of four including two adolescents moved into the vacation house). The weekend was a gift, a time to be removed from the troubles of the world and float in a temporary paradise.

Today was the second part of the gift: the realization that you get to keep it.

kittooseSome clothing is for the fantasy. Part of what I enjoy about my favorite designers is the fantasy they play with (and often undermine). And certain occasions invite us (or allow us, anyhow) to play with fantasy.

Red, white and grey seersucker? Pants and matching jacket? Yes!

On the other hand, when the party’s over, it’s time for a plain, white T.

It’s good to come home.

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.

14 Days of Reflection: On Turning 41 and the Aftermath

When I turned 40, I was a little brat. For 24 hours, nothing could satisfy me.

In retrospect, I was wallowing a little (er, a lot) in what I felt like was the end of an era. And when an era is ending, and you’re panicking, and you think you will turn into an old man overnight, no meal tastes good. No wine tastes good. No bed is comfortable. And you act like a complete brat.

Caution: objects in reflection are grouchier than they appear.

One year ago, about to turn 40. Caution: objects in reflection are grouchier than they appear.

Trust me, I’ve repented and apologized to all concerned parties who were drawn into the gravitational pull of my black-hole of wallowing.

But now I’ve had a year to practice being 40 and there’s been a few surprises. As it turns out, I prefer 40 to 39.

Like learning to play violin, being in your 40s doesn’t sound too great at first. It’s pretty screechy. But with time, you can achieve the right tone.

Once the initial shock subsided, I began to feel a little more confident in my choices. I went to a conference and wore a suit. I sat with students and listened to their problems and shared the kind of perspective that a man in his 40s might have. I wore stuff that clashed on purpose because hey. I’m 40. I can do what I want.

merpywindowAnd silliness – there’s always silliness. And now, it’s even better.

When you’re a teenager, you’re already silly.

When you’re in your 20s and you’re being silly, it’s a little trite.

When you’re in your 30s and you’re being silly, maybe you should act your age.

But when you’re 40 and you’re being silly – you’re showing your commitment to your youth.

This week, I celebrate the lessons I’ve learned by being 40, and count down to even greater changes ahead.

What to wear on an airplane: Vol II — Conference Edition

Click here for “What to wear on an airplane part 1.”

One small (but very cute) suitcase.

One small (but very cute) suitcase.

What to pack for a weekend is made much more complicated when that weekend involves a single small suitcase, 5 hours on a plane, and 4 days of all-day conference.

Me, I’m spending the weekend with a great group of colleagues at a conference for educators. I have one suitcase and need to make it through four days worth of professional-yet-casual outfits. What do I bring?

shirtntie1. Pack a plaid shirt and a cotton/synthetic tie. The plaid shirt will hide plane wrinkles, the tie won’t get creased once you wear it and throw it in your suitcase.

socksairport2. I think of colors as belonging to camps (more on that, here). Decide whether you’re going for browns (yellow, green, orange, etc) or for blacks (red, white, blue, grey, purple). When travelling, I go for blacks. That means black shoes, black belt, and all the red, white, and blue I can stand.


Sorry for the frown. I was flying United.

smiling3. Pack a grey, corduroy blazer and a grey sweater. Swap between them every day. They’ll match everything and keep you warm if your conference is in Pennsylvania in March. 

Fair Isle is fair game for any conference. It stands out, but won't attract unnecessary attention.

Fair Isle is fair game for any conference. It stands out, but won’t attract unnecessary attention.

4. Find a tie which pops, and yet features a classic pattern, like this Fair Isle tie.

5. Dress classy, but be comfy.

6. Be on time for your sessions. Which reminds me…I’m late!

10 Things I Learned from 30 Blog Posts in 30 Days: [30 DAYS OF WRITING: EPISODE 30/30]

The author, after 30 days of blogging: weary but none the worse for wear. So to speak.

The author, after 30 days of blogging: weary but none the worse for wear. So to speak.

This is day 30 of a 30 day New Year’s Resolution.

1. Thomas Edison famously said: Genius is one percent inspiration, ninety nine percent perspiration. I’d recommend a few extra-percent non-perspiring dedication.

2. Doing something important even when you don’t want to, especially when you don’t want to, is one of the marks of maturity.

3. The more creative you act, the more creative you are. Creativity is more about doing than about being.

4. Though ritual sometimes gets a bad rap in the modern world, daily repetition creates space for magic to happen.

5. It’s okay to put things on hold, even things you love, to focus on something special. But then, get back to those other things.

6. Worrying is a great way to paralyze creativity.

7. After exercise, your temperature, your mood, and your outlook improves for hours. True, too, after exercising creativity.

8. Creative expression brings people together. People to creator, people to each other.

9. Once we’re done with school, college, and grad-school, the feeling of “completing” something is rare and wonderful and needs to be cultivated.

10. Succeeding at a challenge you’ve given yourself sets you up for more challenges, more success.

Special thanks to all my readers, all my supporters, and especially to the blogger responsible for (and who supported me through) this month-long adventure.