Timeless Jennifer Aniston Outfits You Should Recreate ASAP

Although Jennifer Aniston might not be the first name that comes to mind when you hear "fashion icon," she's actually the epitome of one. A fashion icon knows what works for them, their best colors, and sticks to timeless looks. While adhering to trends is always worth consideration — if you consider yourself a fashionista — ultimately, it's the classic pieces, like jeans, tees, and blazers, that make someone unforgettable. Something that Aniston has done for herself, via her fashion choices.

Unlike many celebrities, Aniston's looks are timeless. Not only does she rely on staples that are just as relevant now as they were 25 years ago, but she's also figured out how to still wear '90s trends today and made them look perfectly modern. "I'm a 'jeans and flip-flops and tank top' kind of girl," Aniston told Glamour in September 2025 when asked why she'd never attended the Met Gala. "I love dressing up too, but for me it's a mental game of ... 'Let's get dressed up, put on a fancy dress, makeup, get your hair all 'purdy' and go sit in a big room with your peers.'"

While you won't find Aniston at the Met Gala anytime soon, you will find in her wardrobe a treasure trove of timeless outfit formulas that do all the heavy lifting. From the perfect pair of jeans to a casual white tee, Aniston delivers on the classic style front, and recreating her looks is a breeze.

Vest tops are a summer trend that you can easily bring into fall, and while they had their heyday in the 1990s, they've never really gone out of style — and Jennifer Aniston knows it. She rocked a pinstripe vest top and matching pants on the streets of New York City, looking so timelessly chic that it's hard to tell if she was photographed in 1995 or 2025. If this is calling your name, it can easily be duped with a two-piece, pinstriped linen pantsuit. While this outfit would be just as stylish if Aniston had completed it with sneakers, she instead went the route of black pointed-toe heels, giving it a polished look.

Since Marlon Brando wore a white T-shirt with jeans in "A Streetcar Named Desire," it's been a look that every generation has embraced. It may have its roots in rebellion, as something that "bad boys" wore in the 1950s, but today it's an easy go-to for everyone. A quick scroll through Jennifer Aniston's Instagram will show that she's the queen of pairing white T-shirts with jeans, making it look just as cool as James Dean did in "Rebel Without A Cause." All you need is the perfect crew neck tee and your favorite pair of jeans, and you've nailed the outfit.

In 2015, Jennifer Aniston was spotted leaving a hotel in New York layered up with a fedora, heavy scarf, a jacket, and jeans, of course. From head to toe, this is a look that makes just as much sense as it did 10 years ago as it does today, thanks to every element involved. However, the most important part of this outfit is the low-top Chuck Taylors — something everyone should own a pair of. Not only are these iconic kicks one of Michelle Obama's biggest fashion risks of all time, but they can literally be worn with everything. Obama rocked them with a dress from J.Crew, while Aniston is wearing them here with rolled jeans.

While the 1990s made slip dresses popular and fashionable — thank you, Courtney Love — it's people like Jennifer Aniston and the legions of us who won't give them up that keep them in style. As seen on Aniston, a black slip dress always looks good and can be elevated just the right amount with a matching blazer and heels. Aniston obviously loves how she looks in black, having worn countless LBDs that prove the iconic versatility of the outfit. Whether you go for a tea-length black slip dress like Aniston did in NYC, or a mini baby-doll version, you can't go wrong.

The great thing about a photo of Jennifer Aniston and Brad Pitt snapped in 2000 is that, if it weren't for Pitt's wonky goatee, you'd have no idea it was taken two-and-a-half decades ago. For the premiere of "Erin Brockovich," Aniston wore light grey, menswear-inspired pants, a classic white T-shirt, and a beige jacket that looks like it might be leather. Not only do these pieces work extremely well together, but even as separate articles of clothing, they stand the test of time.

While promoting the upcoming season of "The Morning Show," Jennifer Aniston was spotted coming out of her hotel in a white tank top, jeans with a frayed hem, Adidas sneakers, and a black cardigan over her shoulders. Adidas Sambas are the shoe trend that works great with any aesthetic, meaning that if Aniston were wearing a dress or skirt, they'd complement that look as well. If you love the style of frayed hem jeans, but are too scared to do it yourself, already-distressed jeans are an option worth considering when recreating this outfit.

We're jumping back to 2005 with Jen's blazer and bootcut look, but you'd never know it. Jennifer Aniston was photographed outside a hotel wearing fitted, boot-cut jeans, a dark grey button-down shirt, a black blazer, and black pointed-toe heels. Whether you've been wanting to pull off a topless blazer moment without feeling too exposed or need a chic way to prevent a chilly evening, blazers are a must. Although you can't go wrong with a black blazer or any other neutral color, if you're already knee-deep in neutral blazers, then adding a red or pink one to your collection is a wise choice.

In 2018, Jennifer Aniston attended the WE Day California event and was as Aniston as ever in her attire. She wore fitted, rolled jeans — a style that she often does — white tennis sneakers, a double-breasted black blazer, and a graphic tee underneath. While what's on the shirt isn't easy to see (although it might be safe to assume it's related to the event), blazers are an easy way to dress up any casual tee. Whether you're showing off your favorite band, your political leanings, or some cheeky statement, graphic tees are a fun way to try out indie sleaze if you missed it the first time around.

As Jennifer Aniston told Glamour in September 2025, she really is a "'jeans and flip-flops and tank top' kind of girl," and we love her for it. Strolling in the park, albeit not in jeans, she rocked a white tank top and black flip-flop combo, while holding a gray sweater in case the temperature dropped. Although all her timeless outfits are easy to recreate and affordable to do so, this is one you can do for less than $37. All you need is a ribbed tank top, a pair of relaxed-fit, straight-leg pants, a pair of black flip-flops, and voilà! You're in your Jennifer Aniston era.