Chapter2: What to Wear
The long-awaited second chapter of my article “Tricks of the Trade”. See the first post here See the whole category here. There are 3 more chapters, one each week, so get your learn on and check back next Sunday!
Now, get to reading…
Chapter 2: Dressing the part
First, the Disclaimer
I am, by no means a fashion guru. In fact, most of my fashion sense comes from 
reproducing the trends I see on other men. A good practice, I’ve found, is to take a leisurely walk through the ‘high-end’ stores in the mall. These stores usually include Abercrombie & Fitch, The Gap, Structure, etc. Pay attention to what the men in the posters and marketing drops are wearing. This is usually a great indicator of what’s currently popular and considered ‘trendy’. I also highly recommend asking a woman (an impartial friend, acquaintance, or friend’s girlfriend) what looks best on you.
Brand vs. Price
If your clothing brand is important to you, by all means, pick up the latest fashions at these top-dollar stores. If however, you’re like me and don’t want to spend $40 on a pair of boxer shorts… Once you’ve finished making your mental shopping list, hit the local JC Penny, Ross, or other moderately-priced clothing stores and find equivalents to what you’ve picked out for yourself.
Color and Style
The general rule of thumb here is to keep your colors evenly matched (as much as possible). No one will make fun of you for wearing a yellow shirt with khakis or jeans, but leave the green cargo pants at home. Just keep the colors mute and simple, no purple, neon anything, or other wild colors. Another tip: Stay away from pleated pants. They never fit right, and they bunch in the crotch when you sit.
Shoes
Ignoring GQ Magazine (not even going to link those assbags), no man needs more than 4 pair of shoes. Find yourself a nice pair of black shoes, and a pair of brown shoes. These shoes should have laces and be leather or suede. Pick up a nice pair of tennis shoes, not too much color. And get a nice pair of sandals for the beach/pool/Jacuzzi.
T-Shirts
You can’t have too many. Try to buy at least 2 in as many colors as you can find. Screen printed T’s are coming back in style as well. Keep in mind that these are very casual and should be used for those types of occasions only. 90% of the time I wear a solid T-shirt under my ‘going out’ shirt, which is usually a stripped polo, or a long sleeve solid color shirt, with the sleeves rolled up to my elbows.
Dress to impress
Always try to dress for the occasion, which usually means, dress for where you’re going. If it’s the local bar, take it down a notch. Being over-dressed is just as bad as being under-dressed. Safe rule of thumb: The local bar and the Trendy restaurant: jeans, T’s, polo shirts. The cool bookstore: Jeans or pants, long sleeve shirt.