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  • Writer's pictureEvan Wolkenstein

Style-Story: Bill

Over the years, I have gone through my own style growth.

I have learned a great deal: what rules to follow, what rules to break, and how style is more about self and identity and less about cloth and clothes.

I call the process of matching up my outsides to my insides (and maybe stretching both in the process) “Styling-Up.”

“Styling-Up” might be part of someone’s “Style Story” (my nickname for the story that we tell about who we are and how we choose to express ourselves). I’ve been fortunate enough to assist a few in their newest chapters.

As much as I’ve enjoyed the looks on their faces (or their significant others’ faces) as they came out of the dressing room in Styled-Up gear, I’ve found the stories behind the Style-Up to be meaningful and inspirational.

Meet Bill – in his own words. The cartoons are mine.

Style-Story: Bill


8 years ago — a working artist (stage director)…

I had a lot of conflicts around the word “style” and the idea of “fashion,” and I still do, although the process of the “Style-Up” did help with my desire to get past this hang-up.

  1. I have some sort of chip on my shoulder about form vs. function/content — I see that dichotomy everywhere, and I react negatively to any clothing that I interpret as valuing appearance for its own sake or, worse, for the sake of trend.  I’m biased towards clothes that are low-cost and built to last.  This is something I like about the way I relate to clothes, but my rigidity about style has prevented me from developing my own sense of my own style.

  2. I know that everyone including me has a style, whether I like it or not, and I would like to exert more control and self-determination, not to mention self-expression, into my approach to what I wear.


  1. Another style issue for me is my career change 8 years ago from being a working artist (stage director) to becoming a clinical psychologist.

  2. It’s been easy for me to focus on building up a whole new wardrobe of boring business casual clothing because, well, it’s easy, and also satisfies my desire to be “functional” with my clothing purchases, but this has hobbled me in developing any sort of casual outside-of-work wardrobe, especially since I never had any coherent sense of style in this department in the first place.

  3. Coming into my “Style-Up,” my desire was to focus on my casual, evening-out type clothing, face my fear of flash, and not embarrass my wife when we go out on a date.


  1. First of all, I love the clothes I bought.

  2. It’s great to feel proud and secure when I put a piece of clothing on, with confidence that  it’s cool and looks good on me.

  3. The Style-Up gave me the freedom to push my boundaries a bit and wear things that I probably would have rejected as too flashy or “that’s cool, but I could never wear it.”


The “personality” I go to first for inspiration about most anything is Ian Mackaye (Fugazi, Minor Threat).

  1. A lot of what he wears doesn’t fit or doesn’t look very good on him., but I admire his attitude because it embodies integrity, social justice, non-conformity, self-confidence, and a lack of pretension.

The Style-Up

Bad-Ass: the word of the day

During a Style-Up, I listen to the words that guys use to describe a new jacket or some shoes they love. I’ve heard, “cool,” plenty of times, and I’ve heard, “awesome,” and I’ve heard, “amazing.”

Bill’s word of choice was “badass.”

For Bill, “badass” means “attitude intact.” It means decidedly masculine. It can have plenty of flair, but it must be built upon a classic, solid structure.

Bill is as sweet and gentle a guy as you can meet, and a family guy.

This makes him a domestic, styley badass.

Start with the Last Thing you Put On 

The first place to begin Styling-Up is shoes. It’s the most comfortable thing to take a risk with, and the thing that makes the biggest difference. If you don’t buy that, take a look at the picture below, and notice the difference the shoes make.

Bill wanted some shoes to raise his style-game, but he wasn’t going to be impressed by the brand or by fancy details. Rather, he wanted something “badass.”

The first find was a pair of shoes featured a few weeks ago in my post on Top 5 Casual / Styley Shoes: Chuck Taylors with a great, faded blue wash. A pair of Chucks will go with everything, and this color will go with, well, everything else: it’s fun enough to rock with a t-shirt and its subtle enough to wear with chinos and a button-up.

But sometimes it’s date night. Babysitter, check. Reservations at brew house, check. Significant-other looking very fine, check. Time to put away “badass-styley” Chucks, and break out the “styley-badass” (see what I did, there?) Penguin canvas oxford shoes. Oxford shoes are styley. Canvas reminds me think of big sacks of coffee-beans: badass.

Mix up the high and the low, and you have a great pair of kicks to match with nice jeans, a button-up, and a blazer or sweater.

Stripes: Grrrrrrreat. 

There’s a few old style myths that have outlived their function.

Myth: The first is that you shouldn’t wear white pants after labor day.

Reality: I wore white pants last week, and the only people who felt the need to inform me about the “white-pants fashion taboo” were, themselves, dressed in a manner suggesting they had no business telling me what to wear.

No offense.

Myth: horizontal stripes make you look wider.

Reality: big, bold stripes are for bold people. Tony the tiger. Stripes. Badass, and hottest of children cereal icons.

Big stripes build shape and structure into a silhouette, forming a sort of “ladder.” Trust me, this “ladder” invites significant others / attractive cutesters to climb on up and see what else you got goin’ on.

Secret Weapon: The Hybrid Sweater 

On date night (or when you’re out, trying to turn a non-date night into date night), you don’t need to “get lucky.” You need a magical, outer layer that broadcasts confidence tempered with approachability.

For many men, the unstructured blazer does the job, nicely.

Bill was more interested in something equally effective, but less “affected”: a sweater. Sweaters are great because they scream “approachable” — but sometimes too much so. What does a styley, domestic badass wear on date-night?  We hunted the perfect hybrid-beast: the blazer-sweater.

Soft and cuddly like a sweater. Dapper, with collar and lapels.

The white polo: your new “whateva, whateva” shirt

Sometimes (usually) it’s not date night. You’re at the farmers’ market with your kids or picking them up from school – or sitting down for dinner at home.

What does a styley, domestic badass wear, just… whenever?

First of all, dark denim. Levis. Cuffs. Done.

On the one hand, it’s a polo. You can throw it in the wash. You can wear it with your badass styley Chucks or your styley badass canvas oxfords or whatever slick, casual shoes you rock (click here for my top recs).

On the other hand, the iconic Fred Perry Polo has a storied history. Mods wore ’em back in the 60s while thrashing London on their Vespas. What’s more badass styley than a Mod?

Remember when we used to thrash London? Me neither. But the closest I get to it is a white polo.

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? Through the miracle of the interwebs, we can arrange an on-line consultation. You’ll end up with a handful of great items, some new looks, and a spring in your step. Click to Email Me.

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