Dear DC,

An open letter to the fashionably-challenged.

Dear DC,

I've noticed you struggle to dress yourself effectively lately, and I thought rather than cursing the damned darkness, I could light this candle: a weekly blog briefing on some simple steps and guidelines you can use toward making good dressing--and shopping--decisions.

This week's tip:


A few things men need to accept about shopping for clothes:

1. Not everything is going to look right on you
2. You are a different size at every store
3. Your clothes have a huge impact on how people see you

People who work in retail know that if they can get you into a fitting room to try stuff on, you're exponentially more likely to leave their store with a bag and a receipt. That is, until they meet me: I am the guy who pulls one of everything off the rack (with some exception, true) and takes it al back to the fitting room. Why? Because if I didn't:

1. I'd probably buy some really ugly and ill-fitting things
2. I'd never take any risks with color, styles, and fits

Having worked in retail, I can say that one of the great gender divides involves fitting rooms. Frankly, women use them; men don't. Women take loads of options in; men take 1 or 2. I think this is because men tend to shop for an item, like "I need a pair of jeans, so I'll go by jeans," while women may go to the mall with a similar agenda, but are more likely to shop for outfits rather than pieces.

The fitting room is the greatest thing ever. I've saved myself countless dollars by not buying the wrong thing, and I've taken some calculated risks by trying on ugly things that actually look good with a body inside of them.

If something does not fit in the store, I do not buy it! I do not tell myself it will shrink in the wash/can be stretched out on a rack/can be hemmed or pinned or tacked. I've learned from experience it's better not to buy something than to wind up carting it off to Goodwill after just one or two wearings.

You should try multiple sizes of things on to make sure you're fitting yourself correctly. In some stores I am an XL shirt, unless it is short sleeved, in which case I am an L or an M. Sometimes I'm a L shirt, sometimes nothing fits me right. I can't shop at Old Navy--nothing fits me there (I've tried; I like being frugal).

No matter what your body looks like, clothes that fit you correctly are the single most important consideration when getting dressed.

As we take this journey together, DC, I'll return again and again to fit as our touchstone for making good fashion decisions. Until then, your homework: go try something on. Try on something you think looks ugly on the rack! You might just be surprised.


  1. Your clothes have a huge impact on how people see youThe funny thing is, when you're young, you think everyone is looking at you and judging you and whispering about you etc. When you get a little bit older, you realize you don't give a shit what other people think about you. And when you get even older than that, you realize no one was ever thinking about you in the first place. They were, like everyone else, mostly concerned with themselves. It's quite liberating.

  2. Amen, brother. I'm looking forward to more of these letters to the fashionably-challenged. Does D.C. suffer from the plague of saggy-butted skinny jeans on men as well?

  3. This is sound advice, and should perhaps also be a public service announcement here in Cleveland.

  4. Rebecca, I agree with you. When I wrote that, I was probably thinking more about my personal experience. I feel extra pressure to dress professionally for my job because I'm sometimes mistaken for an intern, and I've also not been taken seriously by people who don't recognize the amount of experience I have in this kind of work. If I dressed without considering how people will see me, I would not be taken seriously at all.

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  6. This will undoubtedly help the fashion-challenged: www.youtube.com/watch?v=1jfBGhWo760 (I pity the fool.)

  7. I don't buy anything without trying it on.

    For the first time, I have a job where I have to dress up, and it is weird that my bad fashion sense could actually affect my job performance. I'm working on it.