Over the years, I have gone through my own style growth.
Now, I express myself a little differently than I used to, but more importantly, I have learned a great deal: what rules to follow, what rules to break, and how all of this is much more about self and identity and much 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.”
Sometimes, “Styling-Up” is 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). Actually, lots of people have their own Style Stories. I’ve been fortunate enough to assist a few in their new chapters. And as much as I’ve deeply 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 Robin – in his own words. The cartoons are mine.
Robin K: Data Architect, San Francisco, 34.
What were your feelings about your style “before?” What did you like? What wasn’t working? 
- In 4th grade, [some girl] made fun of my ass… I [still] have beefy thighs… I ride a lot. I have a complex about finding pants I like …and I feel a little silly that a girl said something that’s still with me, 25 years later.
- I felt ignorant… I liked being casual, but I wanted to “grow up” a little. I felt too scruffy. I didn’t feel “put-together.” Now, the other aspects of my life were “put together” – my reputation in my field, I work with good people — but I felt like a slob in my clothing.
- I didn’t understand why I liked some things and not other things; I confused “I don’t like this” with “I’m unfamiliar with this. I don’t understand this.”
- Incremental changes wasn’t working. I needed a neutral party to help me break through…my own bullshit.
What’s the story behind your interest in “Styling Up?”
My mom died in September. There was a big void. I had to re-anchor myself.
- My Mom died in September, and when that happened, I reevaluated a lot of things – “who am I without this very important person in my life?”
I explored spirituality – and being mentally and physically happy.
- I didn’t know who I was: there was a big void – I had to “re-anchor” myself.
- I explored spirituality… being mentally and physically healthy… and since I was reevaluating everything, I also wanted to reevaluate what I was putting on my body every day.
- I didn’t want a “makeover” – but since I was updating my “psychological clothes,” It made sense to update my actual clothes.
- My guard was coming down. What did I have to lose?
Since your Style-up, what have you enjoyed/ noticed / learned?
- While I’ve gotten some good-natured ribbing, I’ve been enjoying compliments – mostly, “You look snazzy!”
The thing that popped was the shoes.
- I notice other people’s style more. And I appreciate shoes, more. I was at a wedding – wearing my new white shirt, this [subtle] tie – but the thing that “popped” was the shoes.
- Slim fit is the shit!
I don’t want to hide under a billowy t-shirt, anymore.
- I don’t want to hide under a billowy t-shirt anymore. I bike, I run, I like being fit. Why wouldn’t I want to look fit?
If you could “channel” the style traits of any personality, who would it be?
- David Bowie. I saw him in concert in the early 2000s – he was in his 50s, wearing a great suit.
David Bowie, circa late 90s.
My grandmother was an elegant dresser and a gracious host.
- That said, my grandmother was an elegant dresser and always looked sharp – and she was a gracious host. She took time with every guest and made sure they felt good about what was going on.
The Style-Up
Robin looks great in this chambray shirt and cotton tie. That’s not surprising since Robin’s modus operandi is casual. Chambray (think: if denim and linen had a baby) is casual-meets-casual classy incarnate. Here, it’s paired with a cotton-tie. To learn more about why cotton-ties are perfect for every occasion, check out this post. Here, the blue-on-blue is simple, and it looks so clean.
Chalk-Stripe Blazer
This “useful-for-everything” outfit can be dressed up with a blazer. No drab wool “suit-jacket” blazer – but rather, an unstructured (no heavy shoulder pads or lining) blazer with a bold pattern. Chalk-stripe. Shirt and blazer from Club Monaco.
Gourmet Denim and Desert Boots
Gourmet Denim and Desert Boots. (Bonus: the socks!)
Robin was already a jeans wearer, but he was rocking the “eh, not sure what else to wear” type – faded, and shapeless. To capitalize on Robin’s callipygean physique, I put him in some gourmet denim, slim, but not skinny — after extolling the virtues of indigo-died, selvage jeans. In short, they look good with everything not because you don’t notice them – but because they look good, period. Club Monaco’s jeans cost as much as a good blazer, but they are well worth it – they can be worn with everything and the material felt ready to serve for years.
Desert Boots are pretty much the most versatile pair of shoes a man can own. Like the dark-indigo jeans, they can compliment a blazer and tie or a t-shirt. They’re comfortable, they’re well made, and they transcend “fashion” – gracing the feet of style-conscious mods as far back as the early 60s.
Functional and Elegant
The boots’ rich, masculine brown played well off Robin’s new Diesel Watch. Diesel makes watches that you shouldn’t wear unless you are the captain of a nuclear submarine, but also, they make some elegant, masculine pieces like this one. It’s functional, but it’s elegant.
Kicks for the Beach, Kicks for the Lounge
Blue isn’t such an exciting color – unless we’re talking SHOES!
Ready for sand and sun.
Two pairs of shoes, besides the Clarks, rounded out the look. On the one hand, canvas Ben Sherman “derby shoes,” combining a wee-bit of class with a beach-ready fabric/sole. It would look great with Robin’s madras-plaid shirt .
On the other hand, since Robin’s new gear fit within a fairly subtle color-palette, a pair of shoes that would grab attention (or, as he calls it above, pop!) seemed in order. Behold, Gordon Rush wingtips in blue leather.
Stay Simple – Slim it Up
White shirt, wool blazer. The fit is the magic.
Here, Robin’s wearing a simple white oxford dress shirt and a wool blazer. But they’re “Styled-Up” because, as Robin says above, “slim is the shit.” If these were a size too large, they’d look like the outfit of that chemistry professor who lives in a secret office behind the bookcase.
Robin will get used to a slight tug in the buttons and around the chest and arms, and everyone around him will gawk and wonder how he makes it look so damn snazzy!
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.
Following this post, Robin wrote his own account of coping with loss. Here, you can read about the journey – one written with love, tenderness, and dare I say, style.
Style For Dorks 
