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:

NO MORE PLEATED KHAKIS!

The majority of men who still own pleated khakis should take them to Goodwill. They aren’t flattering for most shapes and they tend to cause some unfortunate “package draping” of the “man-parts.”

You should wear pleated khakis if:

1. Your waist size is 4 inches larger than your inseam

You should not wear pleated khakis if:

1. You are anyone else.

Here’s why:

The pleats in the khakis create the illusion of length. One of the pleats is always ironed to flow directly into the crease of the pant leg as it runs down the entire length of the leg, punctuated at the leg opening by a cuff. Cuffs do two things: visually, the punctuate the leg and add further stress to the illusion of height; they also add weight to the pant leg to keep the pleats from bunching around the waist.

Flat-front khakis are the right choice for anyone because they are a classic wardrobe staple. They will never go out of style. That makes them a more important purchase than any other kind of pant. Flat front khakis are also more versatile, easier to dress up/dress down with different looks, while their pleated cousins tend to look stuffy, fussy, and less hip.

A CAVEAT

With any item of clothing, fit is the most essential element of style. If your clothes don’t fit you, you may as well wear a barrel. Your pant legs should “break” over the shoe for almost everyone (unless you are uber-hip and wearing a slim-silhouette style suit–if you don’t know what that is, you shouldn’t be doing it).

If your pant leg, while standing, reveals your sock or even part of the opening of your shoe, they are too short. Likewise, they shouldn’t drag on the ground.

Why wear clothes that fit you?

Because a man wearing a good-fitting pair of pants leaves just enough to the imagination–but gives us plenty of options to consider.

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:

TRY IT ON!

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.