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  • Writer's pictureEvan Wolkenstein

Style-Story: Dan

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


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


Style-Story: Dan, School Principal.


I’ve always felt comfortable about my style, mostly because I’ve never given it much thought…  I liked clothes that are basic, comfortable, and generally casual – I’ve tended to place a premium on comfort and function.  The only time I didn’t feel great about my style were when I had to dress up for something, and I never really knew what to do with that.


  1. Recently, I’ve needed to up my game since taking a job that places me more in a public role in my community.  Before, it didn’t matter much if I looked shlumpy when out and about or socializing with friends.

I wanted to see what it would feel like to try something different.  There are many parts of my “self” that I thought were basically formed, or done changing now that I am in my late thirties.  But I was wrong – I am open to trying on different aspects of my self, including trying on different clothes.


I’m excited about the general guidelines/lessons I learned while trying on clothes, and looking forward to applying them in future shopping.  I’ve never gotten so much (any) attention from store employees before, either – that was fun!

You helped me identify a style “goal” that fit me well – a mixture of casual/rugged and “styled up.”

  1. I put together my new “duds” in preparation…to play bass [with] a funk/blues band, and thought my new styled-up look might help give me a little extra attitude. I’m so excited to play music on the regular again!!


  1. My family and I have been watching “The Voice” recently, and I have to admit that I am enamored with Blake Shelton’s style – he always looks comfortable and kind of casual — but also “dressed up” in a masculine way.


The Style-Up


Start at the Ground Floor


Dan is a really thoughtful guy. He knows more about anthropology than most anthropology text-books. And from what little I learned as an undergrad, anthropology is very interested in the rules that cultures live by, giving structure and purpose to life. True to his academic bent, Dan was interested not only in the outcome of Styling-Up, but also in the rules that govern solid style. He seemed pleased to learn that the variations are infinite, but many of the rules are simple. For example:

Satisfyingly simple: start with the shoes.

Like many men, Dan is interested in practical, comfortable, and “approachable” clothes. Not surprisingly, he gravitated to two classics, both “protean” in their ability to add (wait for it) … class and sass — to any outfit: a pair of Chucks, and a pair of Clark’s Original Desert Boots.

In a recent post, I lauded both of these for their flexibility. Paired with a t-shirt and jeans, you’re casual, understated, cool. Paired with a cardigan or blazer, you are classy and hip. Could could have stopped here and called it a day.

But both shoes come in “+1 Flair” options – meaning with just a little more “pop.”

Dan found Chucks in blue leather and a pair of Clarks with a bright orange sole. All the cool of the understated original but with a paradoxical bit of “frowny face nodding respectful expression.”


“Tell her to make me a cambric shirt, / Parsley, sage, rosemary, and thyme.”

The foundation to the upper part of the body is the well-fit shirt. The top two contenders for Styling-Up are the simple, white oxford, and the chambray. Chambray (once called cambric) is that material that looks a little like denim, but lighter. It’s made up of white and a colored fabric (usually blue, grey, or pink) interwoven, and it looks classy and yet – rugged. Masculine.

A chambray shirt paired with dark denim and styley shoes is unstoppable.

Add a thin, knit tie for perfection – classy enough for a nice restaurant, or to casual Friday at work.

If it’s good enough for Simon and Garfunkel to sing about, it’s good enough for me.


The Classy Layer 


Over the chambray shirt, Dan was ready for a classy layer. Sure, sleeves rolled up is great for a faculty meeting or a visit to a classroom, but what about a parents’ meeting? Or when presenting at a conference?

Here comes the power of the unstructured blazer and the cardigan sweater.

Some blazers (see diagram) have shoulder pads and a payer of material between the shell and the lining. This is what gives a suit jacket it’s suit-jackety shape. It’s why you might not wear a suit jacket with jeans. Too formal.

But the unstructured blazer (see diagram) is at the crossroads of classy and cool (for a full post on unstructured blazers, read here). It pairs beautifully with dark denim and a knit tie. And for the odd occasion when you want something a little more casual (jazz concert? Coffee with a friend?), the cardigan does the job.


Hat on? Hats off to you.

Go for a classic pattern. Avoid fussy detailing like excessive stiching, patches, or (shiver) rhinestones.

Like Dan, go for a classic pattern. Avoid fussy detailing like excessive stitching, patches, or (shiver) rhinestones.

Hats can be tricky. On the one hand, the right hat will add flair to an outfit and unify the patterns and colors – like a good tie. On the other hand, a cheap-looking hat (like a cheap-looking tie) looks, well, cheap.

As it turns out, there are some corners that can be cut.

The Tie Bar, for example, offers fantastic knit ties for the cost of a cheap haircut. The thicker weave can obfuscate the fine details that might otherwise betray the quality of a cheap silk tie.

The same is true for hats. Here’s the look we’re avoiding: hats that look like you bought in on the Boardwalk. Dress hats (think smooth hats in black or grey) look very cheap when they’re cheap. Caps in a finely woven fabric can also look cheap.

But if you pick a hat by a company like Original Penguin, Brixton, Goorin Brothers or Ben Sherman, and you get it on sale, it won’t cost much more than a “I-bought-this-hat-along-with-a-2-foot-long-red-alcoholic-drink-in-a-clear, plastic-tube” hat. And if the fabric has a thicker weave (think wool), you might have a keeper.

Incidentally, two details can betray the quality of your hat: the band and the stitching. It’s hard to describe what makes a cheap band or stitching look cheap, but to get you pointed in the right direction, avoid a band that’s too shiny, or a hat where the stitching is crooked or aligns the pattern in the fabric unevenly.

We found a hat by Original Penguin; the material was dense enough to have heft, the quality decent, and it had an awesome, little bit of flair – a patterned kerchief corner peeking out of the band.


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? 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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