1. Trust your gut, not the salesperson

If you feel like the suit jacket is too big, or the shirt collar is a little tight, or the shoes might not look the best with your suits… then shut out the yapping sales associate and double down on your instincts. That said, there are some fantastic sales people working in retail out there. But know that the little voice (or voices) inside of your head should trump theirs.

2. Brown and Blue almost always trump Black

And this is coming from a website that’s one of the few left which still believes in the power of the clean black lace-up. But you’ll get more use out of your brown shoes. Same goes for navy suits, blazers, and top coats when compared to black. Aside from tuxedos and funerals, black suits are all but… dead. Yet most men gravitate towards black suits, sportcoats, and when dress shoe shopping, they’re always going for black.

3. Bar lacing on dress shoes just looks better

Standard criss-cross (which does not, in fact, make you want to jump… jump…) for boots and casuals. Bar-lacing for true oxfords and sleek dress bluchers. It just cleans up the profiles and adds some serious oomph to the sexiness of even less expensive dress shoes. It’s like the grill on a car. A good one goes a long way.

Left: Cleaner, bar lacing (like a football). Right: standard cross style

4. Dry Clean Less

It can get expensive, it can be really harsh on your clothes (especially fused suit jackets and blazers) and unless you’re sweating a ton, you can usually go weeks if not months depending on the level of use. Again, trust your gut. If something is starting to look a little less than perky, has a stain, or you sweated all night in it, get it dry cleaned. But don’t just dry clean for the sake of it.

5. Wear your “good” stuff more

Like all the time. Don’t “save” your favorite shirt, sweater, blazer or shoes for some unknown future event. Wear your stuff. More often than not those favorites spend far too much time in the closet, blowing past wash cycles when you could have worn them. So wear them and enjoy it.

And not just suits. Sweaters, shirts, pants, whatever. But yes, suits and blazers come to mind first. This is almost certainly the #1 issue with why most guys think they don’t look good in so-called “nice” clothes.



Never hurts to try a smaller size. You might be pleasantly surprised.

7. Get a watch repair kit, and swap bands liberally

It’s like getting a whole new watch when you put a different band on a favorite timepiece. And don’t be afraid to ditch the stainless band if you find yourself not wearing a favorite as much anymore. Swap it out for leather or rubber.

8. Well tailored suit jackets, blazers, and sport coats look really, really good.

9 times out of 10 the guy in the jacket is going to look better than the guy in just a shirt and tie. Or, just a shirt and jeans or whatever. They can be super laid back or extremely dressed up. Whatever the type, it’s a piece of armor.

9. Fear-not a totally new combination. Just give it a try.

Grey shirt under a navy suit? Never would have even taken it for a spin. Or a black shirt under a grey suit (cheesy look on some, but not all). Don’t think your navy blazer and jeans have enough contrast between the two? Guess what… doesn’t really need that much. So you’ve assembled this arsenal of awesome duds. Mix and match out of your comfort zone every once in awhile.

10. But at the same time, don’t fear a personal “uniform”

There’s no harm in being the guy that 90% of the time is wearing a blazer with jeans. Or maybe he’s a v-neck over a collared shirt and wool trousers type. Or, a suit, white shirt, and knit tie kind of fellow. Mix it up from time to time, but the bottom line is you know your strengths and what you feel your best in. Wear the hell out of that.

Don’t be afraid to wear what you like often. (Just try & keep your hands out of your pockets some of the time).

BONUS: 11. Dressing well opens so many doors it’s almost unfair

Sure, there’s going to be those who think you’re a snob/snot for wearing what you’re wearing, but if you don’t take yourself too seriously, 99% of the world will give you the benefit of the doubt. Big time. And when people perceive you to be the best version of yourself (or, often even better) then you’ve all but won the game.

Top Photo Credit: Ell Brown