top of page
  • Writer's pictureEvan Wolkenstein

Style Story: Chris K

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.

  1. You can read Robin’s Style-Story here, 

  2. Joe’s Style-Story here

  3. And Andrew’s Style-Story here.

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 Chris – in his own words. The cartoons are mine.

Chris: Database Designer and Published Author, Chapel Hill, 41.


I have a Superman cap I’ve been wearing off and on since I was a grade-schooler, and golly, it’s fantastic.

  1. I’d never really been much for paying attention to clothes. I’ve generally worn things that are comfortable, easy to keep clean, and, well, don’t require too much fussing. Recently, I went through a very Steve Jobs phase. Which isn’t to say I wore a black mock-turtle neck and jeans every day, but I was into very utilitarian, simple clothing (read: solids) that didn’t draw attention to itself (or me). I do have a cool Hugo Boss suit, but how often can you wear a Hugo Boss suit? Well,  every day, I suppose, but I’m not that type’a dude.

  2. That said, I do become very attached to certain pieces of clothing. For example, I have a Superman cap I’ve been wearing since I was a grade-schooler, and by golly, it’s fantastic. You can almost see through the material, it’s worn so thin, and the integrity of the bill has been breached (and supported by paperclips) since the late 90s. This proves that I’m not a heartless, anti-clothing troll, right? I have a heart and sentimentality.

  3. Still, I yearn to look good. Well, naturally—who doesn’t want to look good? I’d already figured that choices about what to wear could directly affect how others (girlfriend, friends, colleagues, potential clients) see me, but I didn’t have the energy to unlock that code. Enter Style For Dorks.


  1. I have a lot of exciting, new things in my life. I’m traveling frequently to New York, to London, to San Francisco—networking and working with creative people—and I thought it would be fun to show up always looking put together, always looking on top of my fashion game.


Before the Style-Up I was a flat glass of milk. After the Style-Up, I’m an effervescent bottle of Italian Soda with a twist of lime.

  1. Well, for one, it was über fun. I wasn’t sure how I was going to feel about it—and sort of prepared to grit my teeth and poo-poo all of Evan’s choices and combinations using my polite coping skills, but once we got going, I enjoyed it. I’m a left-brained programmer in my day job…so it was a nice change, focusing on texture and color and pattern and subjective beauty and how all these things combine to create a look.

  2. I was surprised at how many different combinations you can get from a few select items. I think I have enough varieties here to wear something different every day until the machines become self-aware, none of this is relevant any more and we’ll all flee to underground tunnels and wear silver, polyester bodysuits with numbers on them (I’ll be THX 1138).

  3. I have to admit, after the Style-Up, I have a little extra glide in my stride. Before the Style-Up I was a flat glass of milk. After the Style-Up, I’m an effervescent bottle of Italian Soda with a twist of lime. I want to be seen. I stand a little taller.


Steve McQueen in Bullit or Paul Newman in Cool Hand Luke—both pull off that “effortless stylish” thing.

  1. That’d be Steve McQueen in Bullit or Paul Newman in Cool Hand Luke—both pull off that “effortless stylish” thing. I’ve always been really good at the effortless part, but I’m kind of excited about focusing now on the stylish.

The Style-Up

Slim and Simple:

In a recent interview with J. Weekly, I was asked what a man on a budget could do to Style-Up, and my first piece of advice was to make sure your shirts fit properly – notably, shirts’ shoulder seams must hit right at the shoulder.

Shoulder seams should hit right at — well, the shoulders.

Chris and I started at Banana Republic and picked out 3 staple shirts: chambray, and black gingham.

All three were snugger in the torso than Chris was accustomed to, but a saleswoman watching us remarked, “Looking good! Great fit! I hate it when guys wear their shirts too baggy!”

Going into the Style-Up, Chris (who had read my polemic on the power of the knit tie) warned me: I will not be buying any knit ties.

I reassured him that there would be no knit-tie pushing.

Until he found a sweater he liked and asked what I would advise wearing it with.

Let’s just say that Chris is the proud owner of a fly knit tie.

Through the Denim, Darkly.

Though Chris emerged from the Style-Up with enough outfit options to suit up during his entire upcoming international adventures, he only needed one pair of pants, and, perhaps surprisingly, it’s something he already had.


But all jeans are not created equal, and the best jeans are not the most expensive, and they do not push a fancy, gourmet label.

Rather, the distinguishing feature is that they must be dark denim. Dark denim is not the same as faded bluejeans. They look sharp. They look “grown up.” They never look douchey, and you can wear them with a t-shirt if you’re ready to rock a Paul Newman look, or with a nice shirt and thin tie, if you’re ready to bag a new client with the best barrel-aged Manhattan ever. 

We picked out a pair of slim-fitting, straight leg jeans in an indigo-blue color, and we cuffed them at the bottom so there was no drape.

Chris, time to get comfy with the fact that your shoes are gonna be ogled.

 Eye-popping shoes

Chris likes to wear a pair of hiking boots when he’s taking his kids to the park, but his best leather shoes are sweet oxfords from To Boot New York. They are classy but conservative.

To bring Chris a bit forward into flair-city, we fit him with two pairs of shoes which I was jealous of.

First, he surprised me by pulling from the shelf (I’d like to think it has to do with my comforting presence) a pair of Monk Strap Dress Shoes.

Monk Straps are the flashy cousin to the Oxford. They’ve been making the feet of men fly since European friars rocked them for their foot-protecting, laceless simplicity. Now, paired with dark denim and a stylish shirt-n-tie, they’re a little bit classy and in fact – a little bit dandy.

Monk Straps: Classy with a touch of dandy. And a touch of the best dressed Franciscan Friar in the abbey.

I figured that was it for fine footwear, until Chris laid his eyes on a pair of shoes close to my heart  – blue Allen Edmonds neumoks. I suggested, back in a post on the top five stylish to do with a Tax Refund, that anyone who lays eyes on these shoes might find their eyes welling up in joy – whether for their style or for the fact that they’re union made in Wisconsin.

Their red laces played off the “trust me” socks I’d put in the shopping basket earlier. and though they’re bold in their color, they go with everything.

Blaze it, Sweat It 

Chris wouldn’t have described himself as much of a “blazer and tie guy” … like about every other fellow I’ve done a Style-Up with. And like many of us, the second he found a blazer he liked, it was like he’d just discovered wood-fired margherita pizza with fresh mozzarella and fresh basil. 

Like a pizza from Del Toro, great style is all familiar ingredients – just better. Fresher. And more lovingly made. And the meal, as a result, is fan-fricken-tastic. It’s beyond being simply full at the end of a meal. It’s being moved and delighted and kind of impressed.

We left Banana Republic with a fine pair: an unstructured (no padding, no lining) navy blue blazer and a classy grey blazer. Both items can be paired with shirt and tie for a casual, styley, professional look, but the blue one (with it’s working buttons) can be worn with a white t-shirt, sleeves rolled up, for a rock-star on a nice date look.

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. Drop me a line at stylefordorks at gmail dot com.

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. Drop me a line at stylefordorks at gmail dot com.

2 views0 comments


bottom of page