From Old Money to Y2K Style, the Best Fall Fashion Trends to Try Now
There's never been a better time to experiment with autumn-ready trends as seen on Kendall Jenner, J. Lo and other stars.
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Danielle Directo-Meston
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October 15, 2021 4:18pm
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Whether it’s TikTok’s current obsession with the Old Money aesthetic and Y2K style to the Wild West looks that are still going strong, the most popular fall 2021 fashion trends prove that bygone eras continue to offer fresh wardrobe inspiration. Post-lockdown life inspired many of us to play with our summer style, so why not use the new season as another opportunity to experiment with old-as-new pieces?
Many of the trends that ruled the runways — including fall 2021 and prior — have already been sported by stars such as Jennifer Lopez, Leon Bridges and Pharrell Williams (who separately wore head-to-toe western looks at the Met Gala), while Rihanna, Kendall Jenner and Bella Hadid are among those who are bringing back aughts-era closet staples such as baggy jeans and cropped cardigans.
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Ahead, we’ve rounded up some of the best womenswear and accessories for incorporating the best fall fashion trends into your autumn closet, from chunky Annie Oakley-esque belts (that don’t look too costumey) to the shackets and laid-back tailored pieces that elevate everyday ensembles. Check out our favorite picks — many spotted on Hollywood — below.
If you purchase an independently reviewed product or service through a link on our website, we may receive an affiliate commission.
Trend to Try: Y2K Style
1. H&M Rib-Knit Cardigan
The resurgence of ’90s to aughts fashion is alive and well, and so are the eras’ cozy cardigans. Stars including Kaia Gerber, Bella Hadid and Katie Holmes have paired their cropped cardigans (often as a top) with baggy jeans and midi skirts. This cute rib-knit cardigan is made of a blend of recycled polyester, wool, acrylic and elastane, and can be worn buttoned up over a tank top or solo if you prefer a more daring look.
H&M Rib-Knit Cardigan (reg. $20) $16
2. BP Tube Top
Yes, the minimalist staple from the ’70s that made a resurgence during the ’90s is back once again in yet another generation’s closets. The best tube tops — like this effortless piece from BP, available in several colors — can be paired with a matching blazer and trousers for a more buttoned-up look, or worn with wide-leg denim to balance out the roomier bottoms.
BP. Tube Top $12
3. Majorelle Cropped Sweetheart Ribbed Tube Top
This sweetheart tube top by flirty L.A. label Marjorelle (spotted on stars such as Emily Ratajkowski, Kristin Cavallari and Oliva Culpo) adds texture and playfulness to fall looks, thanks to the contoured ribbed jersey and dainty ruffled hem.
Majorelle Cropped Sweetheart Ribbed Tube Top $118
4. Levi’s High Loose Women’s Jeans
Summer’s loose denim trend continues into the new season, as the extra coverage wears well into the chillier weather. Unsurprisingly, heritage jeanswear brand Levi’s is the purveyor of some of the best baggy jeans for fall, and the label’s High Loose women’s denim is a great option for eco-conscious fashion enthusiasts. Available in light and dark washes, these ’90s-inspired wide-leg jeans are made of Levi’s Cottonized Hemp material that requires less water and pesticides to produce, resulting in cleaner streams and healthier soil. They’re finished with an effortless deconstructed knee for a casual look.
Levi's High Loose Women's Jeans $108
5. Steve Madden Slinky30 Black Sandals
Steve Madden’s chunky platform slide sandals were recently worn by Charli D’Amelio, and the minimalist pair is one of this year’s best fashion trends that’s going strong into fall.
Trend to Try: Ivy League Prep
1. Tory Burch Long-Sleeve Cardigan
Blame it on the return of Gossip Girl for ushering Upper East Sider prepster style back into our wardrobes. TikTok’s Old Money aesthetic (as explained by Vox) has proven to be among the best fall 2021 fashion trends that can be easily pulled off. Throw it back to the Ivy League style of the 20th century with this long-sleeved cardigan by Tory Burch (the queen of New England prep), which offers an effortless way to achieve the look when paired with anything from flared denim to a pleated skirt.
2. Zara Oversize Poplin Shirt
You don’t have to wear luxury brands to get so-called stealth wealth style. When in doubt, go with a crisp white button-down, like this oversized poplin shirt by Zara. Made of ecologically grown cotton (which was produced with earth-friendly natural pesticides and fertilizers), this classic white long-sleeved shirt has a lapel collar, a v-neck and back pleating.
Zara Oversize Poplin Shirt $36
3. Franco Sarto Carolynn Tassel Loafer
Tassels are a signature flourish of Old Money and dark academia style, and these preppy loafers by Franco Sarto blend the classic footwear style with today’s chunky lug heel trend.
Franco Sarto Carolynn Tassel Loafer $89
4. MVMT Signature Square Bracelet Watch
Leave your smartwatch at home and keep time like a Rockefeller (but without the high price tag) with a classically proportioned ticker, like MVMT’s affordable and chic square watch. This minimalist link bracelet watch features Quartz movement, a mineral crystal face and a 24-millimeter rose gold case.
Mvmt Signature Square Bracelet Watch $128
Trend to Try: Loose Tailoring
1. Zara Cropped Lapel Vest
Vests have been a mainstay among rockstars and “It” girls such as Alexa Chung, and it seems she’s bringing the tailored piece back out from her aughts-era closet. She and Kendall Jenner are among the stars who have recently worn vests as tops. This fall-ready cropped option made of recycled polyester will go well with wide-leg pants or jeans with a cardigan.
Zara Cropped Lapel Vest $50
2. Madewell Flannel Flap-Pocket Oversized Ex-Boyfriend Shirt
Shirts as jackets (a.k.a. shackets) are also in for fall. This oversized button-down by Madewell is made of soft and comfy flannel (manufactured in partnership with the Better Cotton Initiative) and is finished with two flap chest pockets.
Madewell Flannel Oversized Ex-Boyfriend Shirt $88
3. The Phluid Project Oversize Patchwork Plaid Cotton Shirt
Patchwork statement pieces (as seen recently on A$AP Rocky at the Met Gala) are also hot this fall, and the Phluid Project’s oversized flannel button-down offers a cool way to merge it with the shacket trend, another one of this season’s most popular silhouettes. It’s stitched from deadstock plaid shirts and finished with snap-front buttons.
The Phluid Project Oversize Patchwork Shirt $78
4. Maeve Reilly x Nasty Gal Oversized Pocket Single Breasted Suit Blazer
Hollywood stylist Maeve Reilly’s new Nasty Gal capsule collection is comprised of the structured-meets-streetwear aesthetic for which she (and clients such as Megan Fox) are known. This oversized blazer (also available in camel) taps into the tailoring trend that works seamlessly in autumn ensembles, especially when worn with the matching wide-leg suit pants.
Maeve Reilly x Nasty Gal Oversized Blazer (reg. $89) $37
Trend to Try: Pumpkin Spice Shades
1. Daily Ritual Women’s Quilted Oversized-Fit Long Coat
Autumn tones like burnt orange, pumpkin, cranberry, caramel and brown are all of-the-moment shades for ushering in the pumpkin spice season. This oversized coat‘s high collar and diamond quilting will keep you warm and stylish through winter.
Daily Ritual Women's Quilted Oversized-Fit Long Coat on Amazon.com
2. Everlane The Cashmere Collared Sweater
Everlane’s effortless cashmere sweater comes in a stylish pecan shade that works seamlessly as a neutral. This comfy piece features a rounded shape, a fixed point collar, blouson sleeves and ribbed detailing, so the elevated silhouette is great for dressing up jeans and wearing in casual office settings.
Everlane The Cashmere Collared Sweater $130
Trend to Try: Statement Barrettes
1. Prada Silver-Tone Logo Barrette
Fashion’s logomania isn’t going away anytime soon, and stars like Lizzo and Gigi Hadid recently took to their tresses to show their designer devotion to Gucci and Prada, respectively. Much like designer belts, statement barrettes are among the best fall 2021 fashion trends to try right now, especially because their versatility makes them blend in with nearly every aesthetic.
These enamel and silver-tone Prada barrettes come in a set of two and feature the luxury Italian fashion house’s iconic inverted triangle logo, and they fasten securely with an easy-to-hide clip.
Courtesy of Moda Operandi
Prada Silver-Tone Logo Barrette $420
2. Scünci Pearl and Stone Clip
Add a pop of pearls to your mane (without breaking your budget) and clip on Scünci’s playful barrettes, which are adorned with faux pearls and crystals and help keep your strands in place.
Scunci Pearl and Stone Clip $10
3. Kitsch x Justine Marjan Rhinestone Snap Clips
Snap hair clips are also back in style — and if you didn’t hold onto your favorite ’90s accessories, these rhinestone accessories from Hollywood hairstylist Justine Marjan’s collaboration with Kitsch will do. (Ariana Grande has embellished her mile-long ponytail with wordy barrettes from the line.)
Kitsch x Justine Marjan Medium Hair Clips $29
4. Gucci Double G Crystal Embellished Hair Clip
If you go gaga over Gucci, showcase your devotion with this charming crystal-embellished hair clip. It’s made of white resin and boasts the Italian luxury fashion house’s signature interlocking ‘G’ logo alongside colorful pink, yellow, green and blue rhinestones.
Gucci Double G Crystal Embellished Chair Clip $490
Trend to Try: Western Wear
1. B-Low the Belt Bri Bri Belt
Fashion is still obsessed with the Wild West, and one way to work the fall 2021 trend into your wardrobe (without going full cowpoke) is with a bold belt. Cinch your waist with this 1.5-inch leather Bri Bri piece by B-Low the Belt (the brand has been worn by Kendall Jenner, Jennifer Lopez and Addison Rae, to name a few) to bring a touch of Annie Oakley to your jeans or your favorite nap dress. There’s also a half-inch-wide option if you prefer skinnier belts.
B-Low the Belt Bri Bri Belt on Amazon.com
2. Lee Frontier Western Button-Front Denim Shirt
Classic western wear brand Lee’s button-down denim shirt is perfect if you don’t want to go too far into giddy-up territory. The two chest pockets and tortoiseshell buttons add a light cowboy touch, and we like the elongated style that makes the shirt work as a shacket, too.
Lee Frontier Western Button Front Denim Shirt $78
3. H&M Smocked Bandeau Dress
From the ruffles and the delicate wildflower print to the smocked bodice, this bohemian bandeau dress — made of 100 percent organic cotton — lets you pull off the Old West aesthetic in a modern-day way.
H&M Smocked Bandeau Dress $20
4. Matisse Suede Arlo Western Bootie
Cowboy boots don’t always have to look costumey, and Matisse’s Suede Arlo boots boast chic Western detailing without looking like you’re on a movie set. This pointed-toe pair has a comfy 2.5-inch block heel and pull-on tabs, and they hit just above the ankle so you can tuck in your skinny jeans.
Matisse Suede Arlo Western Bootie $205
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