18 of Jennifer Aniston’s Best Looks From the ’90s

There is something about ’90s style that just seems to stand out. Of course, those of us who lived through the decade thought all of the looks were beyond cool, but really, it was more than that. The ’90s were known for taking the fashions that came before them and seriously elevating them; for taking casual looks and making them red-carpet worthy. And no star did that better than Jennifer Aniston.

Jennifer was one of the biggest fashion icons of the time period — not just for her clothing choices, but her major hair moments. Seriously, how many of us can say we had a hairstyle named after us? Once upon a time, everyone and anyone asked for the “Rachel cut,” inspired by Jennifer’s Rachel Green character on Friends.

The decade also was the time for the little black dress, and Jennifer had quite a few standout LBD moments. And who could forget her boss woman power suits?

Here, we’ve rounded up 18 of Jennifer’s best looks from throughout the decade for fashion fans to enjoy. Come take a walk down memory lane and reminisce with us.

‘Ferris Bueller’ Look

Like all fashion eras, the 1990s was at first inspired by the decade that preceded it. But there was a shift coming. Jennifer went with a basic white T-shirt, but the ’90s look comes in with the busy patterned skirt. Also, hello cowboy boots! Overall, it’s an outfit that shouldn’t have worked but for some reason, it totally did.

The Mom Jeans

This outfit is very dated, but it’s still a look that could work today — with a few changes, of course, like a more fitted blouse and more updated jeans. But it’s easy-to-wear clothing that any busy mom would throw on before heading to the park with the kids. Of course, Jennifer doesn’t have kids now and she didn’t then, but we still love it.

The ‘Friends’ Look

This is the look that we attribute to Rachel, the character Jennifer played on the iconic TV sitcom. It’s minimal, pairing a plain black T-shirt with a patterned skirt that’s on the longer side. The outfit really could be worn in any decade — it’s timeless in its patterns and fabrics. Yes, we’d wear this today if it was still in our closet.

A Checkered Dress

This fitted dress was what Rachel was rocking on season one, episode three of Friends (titled the “One With the Thumb”). The character was known for her fashion, something she had a talent for since she was a teenager. It’s not a surprise that during the mid-90s, everyone was copying her looks, right down to her hairstyles.

Strappy Foliage Dress

Even when Jennifer was herself and not playing her famous character, she had a way with fashion. Most of her mid-90s outfits were pretty similar — she wore a lot of strappy dresses with triangle-cut necklines. This one here features an ivory-colored fabric with a gold foliage design that still feels fresh even today.

A Red Floor-Length

Something that was really appealing in the ’90s was the sleeveless maxi dress that shifted the focus to the arms instead of the legs (and Jennifer has seriously sculpted biceps from all that yoga). Though black proved to be her favorite color, she wasn’t afraid to wear bold colors or patterns, including this bright red dress from 1995.

Her LBDs

Jennifer knew how to rock a little black dress, and it was one of the looks she ran with a few times throughout the ’90s. And why not? Every occasion was a workable one for this tried-and-true classic. She kept with her signature spaghetti strap styles, proving that sometimes simple is best.

Layering for Days

Jennifer also had a knack for layering in the ’90s, and this is one of those classic looks. Here, she layered a white tank top under a printed strapless dress and tied a knit sweater around her waist. Is this a look we’d rock today? Probably not. But it was the “in” thing back then.

Casual Comfort

The ’90s was a huge moment for the baby T-shirts and flowy pants — especially if the baby-tees had a graphic or a fun phrase emblazoned on the front. It was the look every preteen and teen wanted to rock. And Jennifer’s outfits on Friends definitely helped drive the trend. She was the icon for this look, and while it’s not high fashion, it’s certainly a look that defined the decade.

The LWD Worked, Too

One of Jennifer’s go-to looks in the ’90s was the floor-length and short-sleeved dresses. Often made in stretchy, easy-to-wear fabrics, these looks proved to everyone that we don’t have to sacrifice our comfort for elegance. She did that so well, whether the dress was black, red, or this classic ivory shade.

The Feminine Suit

It’s hard to know how much of the fashion on Friends was driven by Jennifer herself (or the show’s team of stylists). Still, either way, whether she was Jennifer or playing Rachel, people looked to her outfits for inspiration on how to get dressed for the day. And one thing she really knew how to wear confidently was a feminine suit. Bold colors and a fitted skirt and jacket always won.

The Hair Waves

Jennifer was one of the hair icons of the decade. She had a whole style named after her Friends character, and every salon stylist had to learn how to do those classic chunky layers. When she changed up her look to the larger waves seen here at the premiere of Picture Perfect, she sparked yet another new hair trend.

The Barely-There Dress

We all know that Carrie from Sex in the City made the “naked dress” famous, but Jennifer once rocked the same style of dress — though always in black. It didn’t matter whether she chose to wear her long hair down and or swept up in a sleek bun to better show off her shoulders; she made that “barely there” dress look work for her. And this style is so classic it could be worn today, almost 25 years later, and still work.

Smoky Eye, Half-Up Hair Vibes

We know that Jennifer didn’t come up with that half-up, half-down hair look herself, but she was one of the celebrities who always managed to pull it off perfectly. This look also proved that she could tackle any trend. With the right hair texture and some subtle smoky eye makeup, she could easily amp up her appearance.

Princess Leia

Not only was this red-carpet moment huge for Jennifer because she had Brad Pitt on her arm, but her look revealed her surprising style evolution, as she seemed to channel Princess Leia with this edgy ensemble. The subtle see-through panels on her dress and the ringlet curls in her hair were a moment, one of her most memorable from the decade for sure.

Switching the Focus

This look from Jennifer in 1998 flipped the looks she’d been serving up for most of the decade. Instead of baring her arms with thin straps, she made a switch to this long-sleeved, below-the-knee dress — sparking a major trend for pencil skirts everywhere. And of course, every fashionista had to pair her skirt with strappy sandals, à la Jennifer.

A Fabric Upgrade

We’ve seen Jennifer wear strappy black dresses for most of her career. Still, when she attended the People’s Choice Awards in 1999, she opted to upgrade the fabric on her dress, choosing a sleek satin. Again, this is one of those outfits she pulled off in the ’90s that could still be worn today and not look out of place at all.

A Midriff Show

This look is what everyone was talking about at the 1999 Screen Actors Guild Awards. Jennifer somehow made this bandana-as-a-top thing work for the red carpet. After this, everyone became obsessed with showing off their midriffs. Yep, we have her to thank for that!

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