How to: Be the best-dressed man ever, in the history of clothed men

Hey Gents—

Be the best-dressed man in the room*! It’s easy! Follow these five guidelines, and you’ll have the ladies swooning**:

1: Shirt

Remember the Three Bs—Boxy, Billowy, and Blousy. You want plenty of extra fabric around the midsection, as well as excess bunching of the sleeve at the cuff. The more fabric the better, and if your shirt has characteristics of all three Bs, you’re well on your way to an outstanding ensemble.

2a: Pants

When buying pants, make sure to pick one with plenty of room in the thigh area, and make sure it keeps its wide shape all the way to the ankle. If possible, find a pant with at LEAST two pleats—the more, the better—so the leg’s wideness is accentuated. A high-waisted silhouette is preferred; the closer the waistband is to your belly button, the better.

2b: Jeans

You’re going to need a pair of jeans for casual Fridays at the office! Stick with a light stonewash, and just like #2a above, make sure to choose a pair with plenty of room in the thighs. A slight taper at the ankle is preferred, as is a high waist. See the picture to the right as an example.

3: Electronics

You want the world to know you’re well-connected, so if you have any portable electronic devices (iPhone, BlackBerry, pager, Kindle) make sure to purchase a classy leather holster for each one, and clip them to the belt that is holding up your light stonewashed jeans. Your apparent technical prowess is quite becoming and a definite turn-on for all the females in the vicinity, so don’t hide those high-tech tools in your Jansport! Slap ‘em onto your belt!

4: Sweater

Gents, we’re in the middle of winter, so you’re gonna need to bundle up. When choosing a sweater, keep in mind the three Bs from #1. You’ll need to purchase a size larger than your true size to accommodate the extra dress shirt fabric you’re housing underneath. Stick with a boxy shape and make sure it’s not too snug or form-fitting… the bulkier, the better.

5a: Shoes

Your shoes are the pièce de résistance, so choose wisely! Generally, you want a brick-shaped silhouette, so the toe box is as wide as the rest of the shoe. This is best achieved with a square-toe shoe, and the stumpier, the better. Bonus points if you are able to find a square-toe “dress” shoe with a thick, rubber sole. Not only will you get some extra height, you will also gain traction on slippery surfaces.

5b: Socks

When wearing dark pants and black square-toe shoes, throw on a pair of white athletic socks. They add a punch of simplicity and say to the world, “Hey, I’m dressy, but I’m also easy-going and casual.”

There you go, gents. Follow these five(ish) pointers and you will be the best-dressed man in the room… possibly the whole building!

*If you follow these completely tongue-in-cheek guidelines, you will not be the best-dressed man in the room. You most likely will be the worst-dressed, and everyone will be talking about you behind your back.

** The ladies will NOT be swooning. They may, however, be gagging and vomiting.