Go to Hell

One aspect of dressing well is standing apart from other men. Most of the time you can do this just by putting a little effort into how you look, but there are times when you’ll be around other sartorially inclined men and you’ll want to step up your game; or you’ll be in an environment like an office where everyone dresses similarly and you’ll want to stand out a bit.

Most men will see this as an opportunity to wear a different piece of clothing or accessory than everyone else. This is why you see fuzzy hats, makeup and platform boots on guys in clubs, or pocket watches and other oddities on men in the office. Don’t get me wrong, wearing a blazer when everyone else is wearing just a button-up shirt is a good and classic way to stand out, but there’s another aspect a lot of men don’t look at – color.

I’m an advocate of dressing in a timeless and stylish manner instead of just following fashion and trends. That means the articles of clothing and the way they’re cut and fit should be flattering but classic. However, a man still needs to have a sense of fun and a devil-may-care attitude in the way in dresses. Rather than parachute pants, bell bottoms or hipster mustaches, buy classic clothes in go-to-hell colors.


Any guy can wear a loud, colorful or printed shirt. There’s definitely a place for that as well. But if you want to stand out, add some punch in other areas. Start small and work your way up from there.


If you wear a suit or a jacket then a good way to step it up color wise is by adding a pocket square. These are becoming more and more commonplace but the majority of guys who wear them are using a plain-white, pressed square a la Mad Men. Great look, but not a way to catch the eye. In a sea of black, white and navy, more white isn’t going to grab anyone’s attention. A colorful pocket square will make an outfit more casual. It’s a good way to transition into wearing a jacket if you feel stuffy doing so.

Squares are easier to find than I thought. The one on the left was part of a three pack that I got at Target for about five bucks. The one on the right is a silk scarf I found at a thrift store for $2.00. The thing about squares is you have to buy them when you find them, thankfully they’re cheap so it’s easy to do.


Socks are the next step up and are my favorite. I haven’t worn a pair of black dress socks in years. Most people don’t see your feet unless you’re sitting and you either have your legs splayed or crossed, or if you’re walking at a quick pace. This means these will catch the eye without blatantly holding someone’s attention. There doesn’t have to be any rhyme or reason to your sock choices either. Never ever try to match your socks to your square, tie or any other piece of clothing. Matching accessories takes you out of the realm of stylish and into the midst of the sportscaster. Socks – like pocket squares – are actually easier to find on the cheap as well. Target, Old Navy, American Apparel, all of these sell loud socks at decent prices.


The last is the most difficult. Wearing go-to-hell pants is something you can’t do self-consciously. You have to have confidence to pull these off without making them look like a costume. It’s best to start off with colors like I have here. These blue guys are a staple for me in the warmer months and the cranberries are perfect for fall and winter.  If you have the confidence to wear these, you’ll have women approaching you to ask you about them. Just turn on your charm from there. A word of advice about pants like this – wear a plain shirt with them. You don’t want things to be competing. White, grey or navy are about all you can put on with pants like these; and avoid any patterns.


At absolute most, you want two pieces that stand out and one of those should be a smaller piece. If you have more than that going on, you’ll look like a clown. Loud pants and loud shirt – no go. Loud pants and loud socks – doable. Another piece of advice is to keep the patterns and cuts classic. Things like varsity stripes, argyle and gingham can look great with loud colors. If your colors and patterns are unconventional, you’ll look like something out of the 80’s.