Have you ever looked at pictures of some of the more offbeat male fashion looks and wondered if you could rock them, too? From suspenders to elbow patches to cardigan sweaters, style “risks” (if you could even call them that) abound for the unadventurous male, if he’s brave enough to banish his hesitation and try them out.

Luckily for you, Miss Wingman offers a new and recurring feature that serves as a How To guide to aid you in your closet exploits. So, if you’ve ever stared timidly at an outfit and wondered, “Could I pull that off?” this one is for you.

There are 3 basic ways to rock a pair of suspenders, in my opinion. The power broker look, the I’m-Just-Really-Laid-Back-And-Trying-To-Look-Like-I’m-Not-Trying-Too-Hard look, and the ironic hipster I’m-Trying-Way-Too-Hard look. Two of them work, one of them doesn’t. Can you guess which one?

Right, my thoughts exactly.

First up, to please the inner Chuck Bass in all of you (my bad – men don’t watch “Gossip Girl,” here’s a picture to illustrate), suspenders with a suit and a crisp oxford shirt is a great way to go to work.

But, you have to commit to it. It’s a pretty severe, corporate, Patrick Bateman in “American Psycho” kind of look, so if it means making sure your hair is in place with some pomade and that your shoes are polished to a high shine, then so be it. Just don’t have any part of your look be slovenly, or else you’ll throw it off balance.

Also, you have to be a certain type of guy to pull this off – the type of guy who eats high-powered lunches at Harry’s Steakhouse and lives in a loft in Tribeca. Otherwise you might look a little silly walking into your job at Kinko’s looking like Bill Lumbergh in “Office Space.”

Next up we have the Trying-Not-To-Look-Like-I’m-Trying-Too-Hard suspenders look found here:

And also on the casual-yet-dapper guy seen here:

The key to this look is that you have to A) roll up your sleeves a bit and unbutton your top collar button and B) a nice, chunky watch helps polish the look off, too. As long as the suspenders are on the skinnier side – button fastened or clip on, whatever your pleasure – and they’re paired with a slightly rumpled dress shirt or T-shirt look, you’re good to go.

But, beware of our last example, the Ironic Hipster look, found here by the brilliantly roaming Sartorialist:

How you know you’ve overdone it is if you pair it with really skinny pants, Converse sneakers and a fedora hat. One of these alone may not be a problem, all of them together is just too much. And speaking of things to avoid, never EVER rock suspenders shirtless or with a sleeveless undershirt.

This isn’t Chippendales and you aren’t in a naked fireman costume, so cut that s–t out please, thanks. If you really must leave the suspenders hanging down around your waist, I can’t stop you, but in general they’re better up on your shoulders where they belong.

The general idea with suspenders is that you want to embrace the whimsical, add a new accessory to the mix, or even just give a silent “F%*@ you” to belt wearers everywhere, it’s your call. Just don’t overdose on whimsy, and make sure you feel comfortable as well. If you’re not confident when you wear them, it will come through.

Don’t be scared to try out new things, but also don’t be afraid to ask what the right way to approach them is, either. In matters of style, there’s a good way and a bad way to sport everything, trust me. But when it comes to suspenders, they’re not just for holding up your pants anymore, so have a little fun.DAPPER WINGMAN

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