1. Don’t make the rookie mistake of wearing pants that fit.

I can’t tell you how many great fashion games I’ve seen ruined by this one critical error. Make sure when you’re at Costco with Marie looking for jeans, that you get a pair that needs to be rolled up twice at the ankle, and is about three to five inches too wide at the waist.

Here’s a quick test to make sure your pants are the right size: when you’re sitting in the Lay-Z-Boy watching SportsCenter and you get up to go close the screen door Caden left open, you should feel the need to give your pants a good firm upward yank. This means they fit, and it just looks so cool, especially if you can pair it with a good frustrated sigh, or an under the breath “Dog gammit, Caden!”

2. Make sure you’re wearing the “right” Hawaiian shirt.

When shopping for a Hawaiian shirt, you can just grab any old one right off the rack, right? WRONG!

There are a few criteria you need to make sure the shirt meets before it goes into your half of the walk-in closet.

First, is it hibiscus flowers or palm fronds? Palm fronds will totally make you look dated and out of touch, so always go hibiscus. But you’re not out of the woods yet; the number of flowers on the shirt needs to be between five and eight. Fewer than five and you might as well not even be wearing a Hawaiian shirt. More than eight and you’ll look like you’re trying too hard. And finally, before you get any shirt, check the tag to make sure the coupon you printed at home applies to it.

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3. The strap on your sunglasses IS NOT OPTIONAL!!!

Oh, it looks stupid? You know what else looks stupid? Your sunglasses falling off when you bend down to grab a penny off the street to see if you’re missing that year in your collection. Nobody wants to be in that position.

Plus the strap is a great way to put a fun statement on your outfit. Maybe you can buy one that says “Still a stud,” or something simple and classic like “Go Sox!” It’s really up to you.

4. Belts! Belts! Belts!

You gotta have two belts: one formal belt for funerals and weddings, and the other is your everyday belt, which should be no fewer than five years old — and its age HAS TO SHOW. Ideally, your everyday belt should be at the point where the hole you use every day is so stretched and tattered that it’s almost merged with the one next to it.

And remember, adjusting your belt before you do anything is a classic and awesome power move. About to tell the lazy teen at Lowe’s that he sent you to the wrong aisle for ?-inch washers? Tighten that belt, partner. Sitting down to a plate of beef and chili fries at Johnny Rockets? Loosen her up a couple notches. This telegraphs that you’re a big man who’s about to eat a big man meal.

5. Stain your jeans tastefully.

It’s a real pet peeve of mine when I see someone with poorly-stained jeans, or worse still, unstained jeans. It makes me so gosh darn angry.

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Here’s all you need for the perfectly-stained pair of Kirkland denims:

Nothing more. Nothing less. If you follow this tip your jeans are gonna be the talk of the bridge team.

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