Gen X Fashion Trends That Still Feel Chic Today – Glam

Gen X Fashion Trends That Still Feel Chic Today

When it comes to the war of the generations, Gen X tends to slip through the cracks. While boomers can’t seem to grasp the oversized clothes movement that’s dominated the 2020s, and millennials and Gen Z are in a constant battle over skinny jeans, Gen X has largely flown under the radar. Born between 1965 and 1980, Gen X ruled the world — sartorially speaking — between approximately 1985 and 2010, when most were in their teens, 20s, and 30s. So we have them to thank for the reigning styles of the ’90s and ’00s. Now, did they get everything right on the fashion front? No, but no generation does. The important thing is that a few key Gen X trends are still considered the height of style today.

We can’t support every Gen X trend (the low-rise hip huggers of the early aughts come to mind), but their inherent fashion prowess is obvious through enduring staples like the slip dress, aka every minimalist’s dream. Even if you don’t want to rock the ’90s minimalism look that’s been making a comeback since 2023, there are still vintage styles from the era that lean more maximalist. We might have updated the way we wear these retro pieces, but in essence, they’re Gen X trends that might be even cooler today.  

Slip dresses are a staple again

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We can’t talk about Gen X fashion trends without mentioning the slip dress. It doesn’t matter what era you were born in — this is definitely something you should add to your capsule wardrobe. 

Back in the ’90s, this look made frequent appearances in pop culture at the time, whether you were watching “Sex and the City” or keeping up with it girls like Naomi Campbell. The version back then was usually hemmed just below the knee (although maxi slips exist, too) and could have a few different necklines. The spaghetti strap straight neck was the most classic, but in more formal settings, Gen X-ers reached for cowl necks to give the basic slip a little spice. Often, slips were satin, but they could really be any material.

These days, layering is a huge part of the way a slip dress styled. You can make it part of your cooler-weather rotations by pairing it with a leather jacket, a trench, or even a sweater. To make the look less formal, you might layer it over jeans, or to make it really casual, over a long-sleeved tee. On the flip side, dress it up with a blazer and heels. Lace trim is the trendy detail we started adding to our outfits back in 2025, so slips with lace absolutely work. For a similar Gen X-inspired vibe, you could go for a lace-trimmed slip skirt instead of a dress.

Bike shorts are back (with an upgrade)

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Back in 1994, Princess Diana broke the ’90s equivalent of the internet when she was spotted out and about in London in bike shorts. This casual outfit caused such a stir in part because she was the mother of the future king of England, but Gen X-ers at the time took this look in their stride. Bike shorts became one of the biggest hits of the decade, and many paired them with sweaters and athletic pieces the way the late princess did. 

Creating a combo of a form-fitting bottom and loose, oversized top was the done thing at the time, but we now have more exciting sartorial options in our arsenal. Neon bike shorts were all the rage in the ’90s (again, probably thanks to lingering influence from the previous decade), whereas these days, pastels seem to be the trendiest iteration. But plain black works, too!

One of the easiest ways to adapt bike shorts to the 2020s is finishing them off with a sleek heel. You wouldn’t necessarily wear this pairing to a wedding, but it does create a dressier vibe in an elevated streetwear kind of way. To enhance the more formal aspect, consider adding a blazer or even a “going out” blouse or waistcoat. Of course, you can still wear an oversized top, whether that’s a button down, a royal-approved sweatshirt, or even a preppy cardigan. Graphic tees and sneakers are also good pairings if you want more of a casual, retro-coded vibe. 

Bootcut denim has replaced skinny styles once more

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Nothing can divide fashion junkies quite like jeans. While millennials were the poster children for skinny denim in the 2010s, Gen X-ers were all about bootcut styles in the ’90s and ’00s, and Gen Z seems to agree

As with all denim, bootcuts are pretty self-explanatory. They’re slim-fitting towards the waist and along the thigh, and then from the knee they start to barely flare out towards the ankle, leaving room for boots. Younger folks have certainly embraced these jeans, but they’re also popular in the 2020s because Gen X-ers never really let them go. “Never stopped wearing bootcut jeans,” one admitted in a Gen X Reddit thread. “I hated skinny jeans in the 80s, and they were just as ugly in the 2010s.”

Stock-standard bootcut jeans will endure through the 2020s and beyond, but they have also led to the popularity of the even baggier flare jeans. With more width around the ankle, this upgrade is one way to make this Gen X trend feel super modern. If you want to stick with traditional bootcuts, though, try styling them with capsule wardrobe staples like button downs and a trench coat. You could also go for a cropped trench if longer outerwear makes the look feel too heavy, or even a blazer. And contrary to popular belief, you don’t have to wear bootcut jeans with boots; sandals are a great summery pairing, while loafers work with bootcut denim in every season.

Gen X went wild with animal print

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Gen X might not have invented animal prints, but they were certainly wearing them before the younger generations started loving them in the 2020s. Leopard print in particular was a mainstay in the ’90s, and once again, we have icons of the era, including Princess Diana and Melanie “Scary Spice” Brown, to thank for that. 

Back in the day, animal prints appeared anywhere and everywhere. Gen X-ers were known to wear animal-print shirts, outerwear, and even shoes and bags. These patterns tend to make statements, but you can also work them in as part of a quieter, cohesive ‘fit. The key to wearing animal prints in the 2020s is balance; if you’re going for a louder leopard or croc coat, for example, keep the rest of your outfit basic with a classic dress or pair of jeans.

Accessories are one of the best ways for those who prefer a minimalist aesthetic to embrace this Gen X trend. You could simply go for a zebra scarf and keep the rest of your outfit neutral. Leopard-print shoes are having a moment, too. Style mavens are teaming leopard mules with jeans for a casual look, while dressing things up with earthy-toned dresses worn with leopard pumps. On the flip side, you could go all out and lean into the mob wife aesthetic that was trending in 2024, critics be damned. Go big with leopard coats, dresses, and pants. A leopard maxi paired with a leather jacket will always be a classic!

Gen X-approved headbands have made a comeback

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You only have to look back at old footage of it girls from the ’90s to know how prominent headbands were for Gen X. Figures like Carolyn Bessette-Kennedy and cult classics like “Clueless” made them a must-have of the era, and while they dropped in popularity through the noughties and 2010s, they’re back on the hot list in the 2020s

Bessette-Kennedy was known for her go-to tortoiseshell headband, but really, everyone wore this hair accessory in the ’90s, and it’s coming back. Even Ariana Grande is a fan! The acrylic-style printed headband added a little oomph to otherwise basic minimalist outfits back then, while stretchy block color headbands tended to work with a whole range of casual looks. Those comfy cotton headbands in particular first made a comeback in 2023. More elaborate options had a brief moment in the sun in the late noughties, when Blair Waldorf made them a preppy go-to on “Gossip Girl.” But to keep them Gen X-coded, keep in mind the old philosophy that less is more. 

Plain black headbands, even in soft fabric rather than acetate, are stylish add-ons for corporate wear, and this takes a page straight out of the Gen X styling handbook. To keep the look really chic, pair the shade of your headband with the rest of your outfit and have your own monochrome moment. It’s true that Gen X might remember making a few makeup mistakes in their day, but on the fashion front, we owe them a lot.