Menswear Designer Billy Reid Shares His Top Style Advice for Men

Have you ever noticed the guys who love to dole out style advice are often the ones that actually need some themselves? The guys with the real knowledge don’t feel the need to evangelize about how to get great style—you have to ask. That’s exactly what we did when we saw designer Billy Reid backstage at his Spring/Summer 2020 runway shot in Florence, AL, the location of his flagship store and his annual food and music festival, the Shindig.

Reid’s aesthetic—a mix of laid-back Southern roots and sharp New York sensibility—blends loose silhouettes, intricate patterns, and cool, neutral hues. It’s a style that’s born of inspiration and necessity.

“I’ve spent my whole career traveling to New York, Alabama—everywhere,” says Reid. “So I only keep things in my closet that fit me well and will outlast trends.”

Read on for Reid’s tips on building a closet, looking slimmer, and the one thing you should always do before any dressed-up event.

Buy Fewer—Better—Things

Billy’s approach to his closet is the same as his collection: quality over quantity. “It’s better to have high-quality pieces that really fit you well than just a lot of clothes taking up space,” Reid says. When paring down his closet, he asks himself what he would take on a two-week trip if he had to pack right then. Anything that doesn’t fit that mold gets the axe.

“That leaves me with my favorite jeans, my navy blazer, some T-shirts, a suit, exercise clothes, and then some more laid-back items,” he says. “Essentially, I boil it down to just what I need.” Reid wears clothes largely in solid neutrals like navy, black, white, and gray—with some small dashes of color—because they always look great together and will always make for a timeless look.

Essentially, I boil it down to just what I need.

“Of course, you’ll still have that tux you wear once or twice a year, but those everyday essentials can take you a lot of places.”

If you have a massive closet, a good place to start is weeding out anything you haven’t worn for the past year. Then you can start assembling the pieces you definitely want to keep by using Reid’s method.

Don’t Overdo It

A tie bar or a pocket square can add some panache to your look and show off your personal style. However, wear them along with suspenders, a pocket square, a lapel pin, and a chain wallet, and you’ll come across as trying too hard.

“I love accessories,” Reid says. “I think men need them. But stick with just one.”

For example, if you’re wearing a sport coat, adding a pocket square can be a bold statement by itself. The temptation could be to combine it with other pieces, but Billy says the right way to nail the look is to commit to just one accessory and own it.

“You don’t need that extra lapel pin—unless you’re a senator.”

Big Event? Always Wear-Test

If you’ve ever pulled out a jacket or suit before a wedding or ceremony only to find that it doesn’t fit well or isn’t tailored correctly, you probably learned this trick the hard way. Reid suggests that before any notable event—or any time you need to look your best—to wear your planned outfit well in advance.

“When Sean Connery landed the role as 007, he knew he’d be wearing one gray suit a lot, so for weeks before filming he wore it every day. Apparently he even slept in it,” Reid says. “That’s why he looked so relaxed and confident in the film.”

To that end, Reid outfitted Daniel Craig with his iconic peacoats for Skyfall and made the delivery weeks early so Craig could live in them before filming.

Wear-testing will also help you realize if the finer tailoring details—cuffs, hems, length—need tweaking. Shoot to have your look three weeks before the big event and wear it at least twice so your look will say you know how to own a room.

Less Fabric is More Flattering

Tailoring is a specialty of Reid’s, and he knows how the right cut can make you look fit—or fat. To trim down your silhouette, he suggests using less fabric whenever possible. For tops, this means band collars for formal events and Henleys for something more casual.

“Removing a collar makes your neck look longer and creates a slimming effect,” he says. “It’s a trick women use often, but it can be translated into menswear, too.”

The same goes for your pant width. A baggier fit—unless that’s the intended effect—can make your bottom half look heavy, especially in photos.

“On ESPN, the sportscasters often wear slimmer-cut pants that are cut like jeans, because they want that slimmer leg.”

Achieve this same look by opting for slim-fit pants—even on bigger guys. Having no more than 2 to 3 inches of excess fabric at your leg when standing is the perfect way to make your overall shape look slimmer in a flash.

I love accessories. I think men need them. But stick with just one.

Mind Your Proportions

Just as the width of your clothes is essential, so is the length.

“Wearing a jacket that’s too long can weigh you down,” Reid says.

It’s essential to find your own just-right jacket length to even out your proportions. Reid wears his jacket a bit shorter than a typical off-the-rack jacket in his size, but it took him a while to figure out what worked best for him.

The old-school trick is to cup your fingers against your palms to find the spot where your jacket should hit. “It’s not so scientific, but it’ll give you a feel for what’s right.”

For the best results, Reid recommends working with your tailor to experiment with different lengths and find the one that’s right for you.

“Once you train your mind to see the small differences, you’ll start noticing it with all your clothes, and you’ll look better for it.”