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:


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.


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.

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