By Style Girlfriend | Last Updated: Feb 24 2019

As Blinders Month comes to a close, we want to once again encourage you to break out of your pre-conceived notions of what you “can” or “cannot” wear. Today, that means showing you how to wear a vest without looking like you’re wearing a costume. 

In the same way that you can convince yourself not to try a trend, you can convince yourself not to try a classic look that’s too often just worn wrong.

Case in point? The vest.

Because we get what you want to be going for. We really do. You want to look like Paul:

So cool. So casual. So “This ol’ thing?” It’s not matchy-matchy. He doesn’t look like a try-hard.

But then you try the look for yourself and when you look in the mirror, you’re a total Justin:

Okay sure, this picture is from eight years ago, but the one before that is from fifty years ago! And Paul clearly wins the “Who Wore It Better?” face-off!

So we’re showing you how to wear a vest and look natty, not nerdy.

Très cool, not try-hard. Swerve-y not scary. Okay, okay. You get the idea.

What’s the difference between a vest and a waistcoat?

The short answer? Nothing.

The longer answer? Still nothing, really, but it’s Brits who tend to call it a waistcoat, while Americans generally refer to this sleeveless garment that covers a man’s torso as a vest.

Because we’re stuffed to the brim with Americans here at SG HQ, we’ll stick to vest, but feel free to call it whatever you like, so long as you don’t adopt a fake accent to do so.

Is wearing a vest in style?

Don’t get it twisted. A vest is not a trend. It’s been around a long time, and continues to work for those with the know-how and confidence to pull it off.

If you pluck Sir Paul, looking handsome in his white shirt, dark vest and pinstripe pants, from the picture above and show it to the one person in the world who doesn’t know who the Beatles are (there’s gotta be one, right?). I guarantee they won’t be able to place the time period. That’s because, when worn right, a vest feels fresh, not dated.

How to wear a vest

With dress pants and a denim jacket

SG Says: Hello! How great does this look? So great. And modern, right? That’s thanks to the dark-rinse denim jacket subbing in for a sport coat, and those fluorescent bright-white sneakers. Totally youthful, yet totally sophisticated.

With a textured topcoat

SG Says: A vest doesn’t have to look extracted from a three-piece suit! You can wear a puffer or quilted vest under more formal outerwear for a yin-yang situation that looks balanced and modern at the same time.

With jeans and an OCBD

SG Says: While this seems like perhaps the most straightforward way to wear a vest, proceed with caution as you can veer into “middle school teacher who thinks the kids like him more than they really do” territory pretty quick. A vest in a more textured fabric – like herringbone or tweed can handle details like a notch lapel or fancy buttons.

Just play the rest of the outfit simple.Keep the shirt tucked in and the vest buttoned except for the bottom button.  Add a dark-rinse pair of jeans and an oxford shirt, and you’re good to go.

You could also dress it up with trousers in a coordinating but not matching color. Nothing worse than two greys who’ve never met before.

With chinos and a dress boot

SG Says: Say it with me guys…waistcoats are not to be worn completely unbuttoned, but do keep the bottom button unbuttoned. 

Grab your favorite earth toned chinos (think olive green, burgundy, or brown) and a crisp shirt. Since this is a casual version of a traditionally dressy piece, make sure to round out the look with stylish details like a metal screw bracelet and striped socks.

Finding the best vest

Fit and fabric are key. You don’t want to look like you’re wearing either a waist-nipping corset or an unwieldy life jacket. When it comes to fabric, a more traditional vest with texture will make styling an outfit easier as it has a distinct look that lets people know you didn’t simply toss the other two pieces of a three-piece suit.

When it comes to quilted and puffer numbers, you have some wiggle room (literally) when it comes to sizing, but keep things on the slimmer side for a streamlined look.

Ready to turn up the style on your suiting separates?

If you’re ready to take the blinders off your winter wardrobe go-to’s, but you dread the thought of shopping for it…why not let Team SG shop for you?

Let us rescue you from shopping fatigue and sartorial apathy. With our online personal shopping service, we can promise the kind of dedicated attention that will make you feel like the best, most stylish version of the awesome guy you already are! We’ll also help you figure out how to wear your new clothes with the things you already own.

If you’re ready for a shopping plan that’ll save you time, energy, and your sanity, give us a shout.