Married to Your Wardrobe Part 1


An account of the author’s shifts in clothing choice over his collegiate years (to the best of his memorized ability).

Pre-2005 (Pre-college and Freshman year)

Just like any other clueless freshman schlub entering campus for the first time.

  • “I have no interest in men’s clothing—and it shows” 
  • Normal outfit: T-shirt into jeans with some pair of Nikes
  • Jackets: Ill-fitting hoodies and zip-ups made to repel water
  • Shirts: T-shirts (of course)
  • Pants: Ill-fitting Levi’s
  • Shoes: Anything I liked from Eastbay magazines (where you buy sport shoes)

Fall 2005 – Spring 2006 (Sophomore year)

My purchase of Diesel Zathan 772s started my ongoing obsession with male fashion (read more about that first purchase here).

All I had were the jeans but didn’t need much more than the same tees and a new pair of high top Converses to make it work.

I started buying vintage ties but didn’t have any shirts to wear them with yet. This would begin a side project of buying clothes far and unrealistically in advance which I still carry to this day.

  • “I own $200 jeans—and that’s it” 
  • Normal outfit: Hoody over T-shirt into bootcut jeans with Converses
  • Jackets: Slightly better fitting hoodies, a skinny cord blazer I got at a vintage shop, and a beaten up brown “leather” bomber off eBay
  • Shirts: Still T-shirts
  • Ties: My first “slim” ties (a bunch of knobby vintage 70’s and 80’s ties from eBay)
  • Pants: Diesels
  • Shoes: Converse high tops (the hemp versions) and used black and brown cap-toes from eBay

Fall 2006- Spring 2007 (Junior year)

This was a huge change for me.

I finally got “jackets” to set a daily uniform.

I picked up my first “cool” military jacket, raw denim, sweaters, and peacoat in the fall and finally was able to land a set of “slim” collared shirts from H&M (off eBay and used, of course).

The cotton navy military jacket was from UO and fit perfectly off the rack. It had super high armholes, skinny sleeves, and in lightweight cotton (even had the beautiful addition of lining). I’d end up wearing it frequently for approximately 10 more years (until I finally replaced it with a nylon Burberry version in green). It was that good off the rack.

You could wear it with a tee or a collared shirt and it’d dress the tee up or the shirt down. Balanced out tucking in your shirt as well (which normally looks too “put together” with most any other bombers or zip ups).

The wool peacoat subbed in for that jacket when the weather turned down, and it allowed me to carry the same look simply by changing my jacket for a warmer one.

Black Sambas completed the outfit by giving me a dark shoe that was more “muted” and “slim” than Converses.

So you can see at this point I was going for a daily outfit based on a navy jacket, collared shirt, solid dark navy jeans, and black shoes—like a college version of a suit. 

But it was the purchase of the collared shirts that “fit me” that completed this year. I could wear the same type of shirt everyday, tuck it in, and look “refined”—all without any thought as to what I’d wear as a shirt in the morning.

Now you have to understand how hard it was to source fitted shirts back in this day. Seattle didn’t have an H&M or Zara, and J Crew didn’t push their “slim” line until three or four years later.

Even “fitted” shirts from local retailers had armholes and sleeves so large it wouldn’t make sense to tailor them. And I didn’t discover the secret of tailoring my shirts for a few more years.

GQ was heavily pushing “fitted tucked in shirts” but it wouldn’t be until 2010 that it diffused into J Crew and Club Monaco (where I could finally walk in a store and walk out with a perfectly fitting shirt for under $70) and until 2012 it diffused finally into everyday department stores like JC Penney and Macys (where your average guy who hates buying clothes is now automatically fashionable because he is forced to buy things that fit him).

As I entered Junior year, I can say no one on campus had anywhere the same shirt and jacket fits as me and of course, not even Diesels yet either.

I didn’t need anything other than two “outfits” and was world’s beyond where I started.

  • “I tucked in my shirt—and the shirt fit”  
  • “I don’t just own one v-neck sweater—I own two” 
  • Normal outfit: Military jacket over tucked in collared shirt into slim raw denim with black Sambas
  • Secondary outfit: Peacoat over wool v-neck into slim raw denim with Converses
  • Jackets: My first military jacket (from Urban Outfitters), my first wool peacoat (an ill-fitting Marc New York—not to be mistaken with Marc Jacobs—from Bluefly) which was the first piece I tailored
  • Blazers: My first “slim” blazer (a “perfect-off-the-rack-fitting” two button Marc Jacobs navy cotton/wool blend from Barneys—ironically I put this on today and it fits horribly but at the time and 10 lbs heavier it fit “perfect”)
  • Shirts: My first “slim” collared shirts (I got a bunch of used H&M shirts off of eBay and second hand stores), white v-neck tees, and American Apparel v-neck tees
  • Sweaters: My first “slim” v-necks (gray and camel colored from J Crew)
  • Pants: My first “raw denim” (Nudie Slim Jims in “Greencast”)
  • Shoes: Black Adidas Sambas and still the same Converses

Fall 2007- Spring 2008 (Senior year)

This was less of a major change and more of small additions but still created immense flexibility in my wardrobe.

I started thinking in terms of “light jackets” that the common populace wore but in slightly skinnier fits and muted colors.

This would be to take what everyone else was wearing but find a version more suitable to collared shirts—so dressing the most casual outwear up one level. I’d exploit this habit of re-approaching and upgrading casual jackets that “unstylish” men wore for nearly another decade.

So I picked up a paper thin windbreaker, paper thin hoody, and a light cotton cardigan that both doubled as “stylish” replacements for my peacoat for the other nine months of the year.

And also purchased my first “skin tight” raw denim that stacked at the heel (purchased by one of the first ventures of the company I’d eventually work for after college and still as I write this post).

The biggest change would be a pair of “cool boat shoes” that along with the skin tight denim gave me a “look” no one on campus had. Though nowadays this look skinny jean + boat shoe is completely common fare (Vampire Weekend spread this look with the drop of their self-titled debut in this very same year, but I was wearing this shit before I even bought that album or saw their videos).

Really, guys didn’t mass purchase boat shoes for a few more years (and I’m sure you remember when it hit critical mass).

I didn’t have to change my shirts and suddenly my fits became exponentially more unique than before.

One way to think of this was my “college suit” outfit went one level more casual with the solid windbreaker/hoody jacket up top but still retaining the collared shirts underneath and adding even better, darker, slimmer denim below. More casual on top but dressier on bottom for contrast—so it was like a college weekend suit. 

And this strategy of dressing down the top or bottom to further accentuate yet still soften the formality of something opposite would be another habit I’d carry into the next decade.

The university crowd was now getting into fitted denim (definitely more 7s and Diesels on campus), but they were still behind shirts and jackets. And even further behind getting even tighter fitting denim under everything (and I’m sure you remember when those hit critical mass as well).

  • “I own a third sweater—and yes it’s a cardigan”
  • “My pants are so much tighter than yours—and even more expensive” 
  • Normal outfit: Hoodless windbreaker over cardigan over collared shirt into skin tight raw denim with boat shoes
  • Secondary outfit: Slim hoody over collared shirt into skin tight raw denim with Sambas
  • Jackets: My first “spring” windbreaker (an amazing thin navy nylon bomber from American Apparel) and my first “slim” hoody (an amazing super thin brown cotton one also from AA—this would actually begin a string of paper thin AA hoody purchases that eventually founded my now “iconic” post-2012 Seattle look, more on that later)
  • Shirts: Same used H&M shirts
  • Jeans: My first “skin tight” raw denim ($320 “fair trade” organic Indian supima cotton indigo by Sling & Stone)
  • Sweaters: My first cardigan (an amazing cotton gray piece from American Apparel)
  • Shoes: New boat shoes, same Sambas and Converse