The big boys' guide of how to dress

The original Big Boy? photo: gasolinealleyantiques.com

Since the inception of this column several people have asked me about clothing for big boys. In fact, as part of his last answer to me in my interview with Chris Glass from Wire & Twine he asked that I help him retire his current wardrobe. I've given this a lot of thought ('cause that's what I do) and I've come up with this: instead of suggesting specific items to clutter your wardrobe I'll provide some guidelines.

On this particular subject I consider myself an expert. At 18 years of age I weighed 340 pounds. Since then my weight has fluctuated between 180 and 280 with an estimated median of about 250. 250 seems to be where I'm most comfortable regardless of what that stupid BMI thing says.

The most important thing to keep in mind is confidence. Diffidence, no matter how well dressed, is not very attractive. Only once you are comfortable in your own skin can the outside world see the superlative qualities your momma always said you have (I am completely aware that this is easier said than done, but if I can do it so can you).

Second to a little confidence is buying things that actually fit you correctly. By correctly, I mean not just around the middle, but everywhere.

When buying a shirt, make sure you try it on. Be certain the shoulders are wide enough and the neck is big enough around so you can button it. If it's a pull-over, the neck should fit snugly but not so tight that it's uncomfortable. A tight collar will nag you endlessly and distract you from looking your best. My number one tip for shirts, especially any shirt you plan on tucking in, is to make sure that when tucked in it stays that way. While in the fitting room, tuck that bad boy in and put both arms over your head. If the sides stay tucked in you're good to go.

In regard to pants, the fit can be a bit trickier. Often times, big boys have flat behinds and round bellies. Wrapping a pair of pants around those shapes is no easy task, so patience is essential here.

Firstly, don't fight the pants. Depending on how they are cut some pants are going to ride high (close to your bellybutton) and some low (around your hips). I find that high riding pants tend to slip down and look droopy which means you'll spend an awful lot of time yanking them up which eventually kills your belt loop(s) and then you'll need new pants. No fun. Pants that ride an inch or so above your crack should come around nicely in the front riding on or slightly above your pelvis. In this position they shouldn't slide down too much which will mean less hitching and fewer trips to the men's room to re-tuck your shirt.

Once you get good at getting the right size the rest should be easy.

Here's a few things to remember when shopping for the right size:

• Pleats on pants are a no-no for the big boy. They tend to balloon and make you look bigger than you are.
• Avoid the urge to buy shirts that are too big for you. An oversized shirt will make you look unkempt.
• Consider having tailored the clothes you buy to make you look your best. It's better to spend a little more if your "Sunday best" fits you best. This usually costs $15-$20 per garment.
• Stripes should be vertical, not horizontal.
• Buy straight leg pants to avoid appearing wedge shaped from ankle to waist.
• If you have a lot of things to carry (smartphone, keys, MP3 player), consider getting a man bag to carry it all.
• Wear an undershirt. Big dudes generally sweat more than little dudes. The whole world doesn't want to know about your juicy armpits.
• Think Johnny Cash. Dark clothes attract less attention than light ones and hide stains better too.