We tend to remember the icons of 90s fashion and how effortless their look seemed. Think of Keanu Reeves and Tom Cruise when they were still young; Kurt Cobain and Tupac Shakur when they were still alive. Those guys looked great. Their impact on men’s style continues to this day.

But for every guy in the 90s who looked good, there were dozens who looked ridiculous. There’s a thin line between grunge style and looking like a slob. In the 90s, some guys wore baggy pants and looked cool. Others looked imbeciles because they had to hold their pants up with one hand when they walked. There were guys who looked like gangsta rappers and, embarrassingly, there were other guys who looked like suburban middle-schoolers trying to look like gangsta rappers.

In this article, we’ll explain what 90s fashion items for men are back in style, and we’ll guide you through how and where to wear them.

Casual and comfortable

One key to understanding 90s fashion is to remember that it wasn’t about dressing nicely. Seldom did style icons of the 90s look dressed up. They didn’t look “nice” as much as they looked nice and comfortable.

Joanna Medeiros, a stylist with Taelor, says that emphasis on comfort suggests guys should take a cautious approach to 90s clothes. 

“90s fashion in the workplace just feels too casual,” she said. “I probably wouldn’t send a customer 90s clothes for work.” But if you want to explore 90s fashion for weekend wear, there's a right way and a wrong way to do it. You can blend 90s clothes with other pieces that have a more modern look, Joanna says. “That could be fine on the right person,” she said. 

Scott Shapiro, another Taelor stylist, agrees with that approach. 

“I think it's good to take little bits and pieces from the era and incorporate them into your wardrobe, but I wouldn't go full-blown 90s revival because that looks like a costume,” he said.

So if you’re going to try your hand at 90s style, remember that such clothes are for when comfort is key. In the 2020s, that means weekends, date nights, etc. You’ll want to avoid going to work dressed as if you were going to a 90s costume party.

With that said, let’s look at some of the key items from 90s fashion for men that are back in style.

Bomber jackets

Left: CIVIL SOCIETY TAN QUILTED ZIP UP BOMBER JACKET /Middle: RNT 23 BLACK BOMBER JACKET /Right: CIVIL SOCIETY GREY/BLACK HERRINGBONE KNIT BOMBER JACKET

Bombers return to style with some regularity. Today’s versions tend to be made with better materials than were common in the 90s. But the key difference is that 90s bombers tended to be oversized.

By all means, you should wear bombers when appropriate. But you may want to consult with your stylist before wearing a jacket with lots of extra room. That can be a flattering look on some body types, but less so on others.

Cargo pants

Left: JACK & JONES CARAMEL BROWN TAPERED CARGO PANTS /Right：BILLY BELT OLIVE GREEN CARGO PANTS

Melissa Slavick, a Taelor stylist, says the pants that defined the 90s are in style again … but different than before. “Cargo pants are coming back. But instead of being oversized, it's more of a straight-fit cargo where there's not a million pockets on them,” she said. 

And unlike the 90s, the pockets on today’s cargo pants are never meant to be functional. “They're more just for style and a little bit of added flair,” she said. “But please keep them empty. Do not add more weight or bulge to your legs at all.”

Shirts of many colors

Melissa says neon is back. But unlike in the 90s, you’ll only want neon accents, not giant neon prints, on shirts and jackets. And always pair 90s style colors or prints with something considerably less flashy. “There's definitely elevated ways to wear them. When you wear a jacket with a big pattern on it, you want a shirt in a muted, solid color,” she said. “You don't want pattern on pattern on pattern. It just hurts the eye to look at it.”

Left：BONOBOS TAN AND BURGUNDY STRETCH SLIM PLAID FLANNEL SHIRT /Right：BONOBOS OLIVE BLACK STRETCH SLIM CHECK FLANNEL SHIRT

Colorblock polos from the 90s have also made a comeback, according to Scott. And the key to wearing them today is to pair them with non-colorful, non-bulky pants. The same is true of flannel shirts –  perhaps the most recognizable of 90s men’s fashion. 

Right：DONATO TAN TAPERED CUT LIGHTWEIGHT CHINO /Left：DONATO BLUE GREY TAPERED CUT LIGHTWEIGHT CHINO

“There's a way to wear these so it doesn't feel too literal. Maybe throw on a flannel but then pair it with a really nice chino to keep it modern,” he said.

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