Wardrobe Makeover... Sort Of

I was sitting in a Starbucks last Friday somewhere in North Carolina and it dawned on me: I look like a bum. A beach bum, to be more specific.

A woman roughly 30 years in age sits down on the leather armchair beside me. She's beautiful. She smelled fantastic. And she was dressed in black and gray business attire that was both respectful and drop-dead sexy all at once. Kristin has outfits like this, only I never see her in them because I'm asleep when she leaves for work and she quickly changes out of them when she comes home to be more comfortable. And speaking of Kristin, it had been 9 days since I had seen her. I was attuned to the presence of females -- a form of the species that is uniquely absent from the studio I was working at.

I continued to hammer away at the manuscript unfolding on my laptop, pausing every now and then to take another deep breath of that fantastic scent wafting my way on the air-conditioned breeze in the cafe. And I suddenly realized that if I were single and I were to approach this woman, I'd probably have no shot of adding her to my cellphone's contacts list on account of how I look. She: a professional something. Me: something less so.

I was wearing shorts, t-shirt, ballcap, and flip-flops just like always.

It's a product of working from home for 8 years. I don't need to dress up so I don't. And even when I am on-site, the outfit I just described is also the costume of choice of the professional game developer. I took a small carry-on suitcase with me, filled one-third of it with an X360 devkit and power-brick and filled in around it with an assortment of shorts and tees I picked up at races. I added a pair of jeans and a single short-sleeve linen button-down in case we went out to a nicer dinner, but that's it. This lasted me for 10 days. Yes, I brought plenty of underwear.

I did end up engaging in some brief smalltalk with Ms. Sexy to my right on account of a swarm of houseflies that began dive-bombing our drinks. She was nice. And maybe my earlier comment wouldn't have been true. Nevertheless, I couldn't help but feel that maybe, just maybe, it's high time I start dressing a little nicer. Not because I want to meet women in coffee shops, hell no, but perhaps to just look a little more professional in general. Or so maybe when I meet Kristin for lunch, I don't feel completely out of place.

A lot of people subscribe to the theory that you shouldn't dress for the job you have, but for the one you want. I have the job I want, so where does that leave me? I'll tell you. It leaves me working and running errands in the same "business attire" I used to wear to flip cheesesteaks at Little Mac's on the Jersey Shore when I was a teen, that's where.

Comfort rules my selection process when I'm getting dressed. Style comes second. My clothes fit loosely, and are lightweight. If I'm cold, I throw on down-filled slippers and a fleece pullover. Sandals, shorts, long-sleeve fleece. It's not that I don't like dressing a little nicer, but that I get very, very angry when I'm trying to find clothes that meet my conditions of comfort first, style second.

Like me, Kristin hates to go clothes shopping. Absolutely hates it. She also hates to "splurge" or "treat herself" to anything. You can see how this poses a problem in a household with the typical thirty-something guy who likes expensive toys. Namely me. Fortunately while I was away I was able to convince her to take a wad of cash and go shopping with her friend Kari. Kari likes to go shopping, has very good taste, helps Kristin find clothes that look really good on her, but is also not Christyann who thinks nothing of dropping hundreds on a pint-sized purse with a billboard-sized Italian logo. Men, this is key: you must identify the proper shopping companion for your woman.

Kristin picked me up at the airport Saturday night and looked stunning. I literally had to do a double-take to see if it was really her. And to be honest, I didn't care who it was: I was going home with this Hybrid Civic driving hottie regardless. Luckily, it was my wife.

On the way home, after multiple expresses of astonishment about her new clothes (and hair... you got to remember to commment on the hair, guys), I told her about my revelation in the coffee shop. She understood, but still offered the standard "I think you always look nice" bullshit that spouses are required to feed one another when they haven't seen each other in 11 days. Yet, she understood and agreed to go shopping with me on Sunday.

So yesterday we went shopping and as we went from store to store, I got angrier and angrier. For starters, there is no middle-ground without wading into the extremely preppified waters of the Chads and Parkers of the world. It seems that men's clothes comes in three flavors: super casual college rags, Hamptons-wear, or business attire.

I was willing to give every men's clothier in Bellevue Square a shot. I even went into Brooks Brothers (only to leave 2 minutes later mumbling incoherent sentences with the words "not ever" and "before I'm 60"). In each and every store, I recited the same thing: I'm a shorts-and-tee shirt kind of guy looking for some nicer clothes, but I don't want anything too formal or too preppy. In store after store, I was "helped" by a teenager whose fashion sense (or was it my own?) and ability to listen to my request was impeded by their willingness to "wear whatever" and "break rules".

Good grief.

I finally came to one store that had a bunch of nice shirts that I really liked. They were $450 each and I quickly vacated the premises.

Fortunately, just when I had all but given up hope (and strangled one or two people in Express for Men), I went back to the old standby: Banana Republic. A twenty-something sales associate offered immediate help, took me straight away to a pair of pants that, true to his word, are the most comfortable pants I've ever worn and also look very nice without being preppy. He then found shirt after shirt for me that fit exactly what I was looking for. He offered tips on coordinating, on which ones I could wear with nice jeans, which shirts to wear tucked or untucked. I know some of you are laughing right now, but trust me, when you make a point of never having to wear a collared shirt in nearly a decade, this sort of help comes in handy.

To complete my new ensemble, I did something I always wanted to: I bought a pair of brown slip-on Clarks. This is what walking on the clouds of heaven must feel like. As comfortable as my Rockports are, these are off the charts in comfort. And best of all, no laces! Which is a good thing since I usually double-knot my shoes then pull them on and off without ever untying them for years anyway.

So, last night, Kristin and I came home and started cleaning out the closet. The closet had no room for our new clothes, but not because we have tons of things to wear. Instead, it's because we have tons of clothing from 10-15 years ago. We filled a half-dozen large shopping bags with clothes that we had since we were in college (we graduated in 1997) or that we bought for our honeymoon 11 years ago. Kristin finally got rid of these hideous business suits she used to interview in when we were first starting out and I, well, I had a ton of stuff that I hadn't even considered trying on in well over 6 years.

This morning, I sprang out of bed ready to get dressed in some of my new clothes. After all, I have an 11:30 meeting at Microsoft that I have to at least put pants on for.

I chose jeans (that I've had for several years, but rarely wear), a short-sleeve collared shirt (that I bought last summer), and my new Clarks shoes. I completed the ensemble with the micro-fleece vest I bought at the Moots factory a few weeks ago. After all, no outfit is complete in the PNW without a splash of fleece.

Some things never change.