If you’re anything like me, you’ve spent the last one and a half years rewatching the classic romcoms of the late ’90s and early ’00s. When everything feels like it’s in disarray, there’s nothing more comforting than escaping into a world of cliché meet-cutes, dramatic proclamations of love and guaranteed storybook endings.
As the rest of the world invested their time in dramatic thrillers and cliffhanger-laden series (Squid Games, I’m looking at you), I happily retreated to an alternate reality before lockdowns, global pandemics or even social media existed. And while the saccharine, completely unrealistic storylines were enough to keep me around, I found myself staying for the fashion. I quickly discovered watching ’90s romcoms was more than just a tool for escapism—it was also a source of new (old) outfit inspiration, from Julia Roberts's leather-blazer-and-beret combo in Notting Hill to Meg Ryan’s bookstore-chic attire in You’ve Got Mail.
Keep scrolling to discover the autumn outfit ideas I plan to copy from ’90s romcoms, including Parent Trap, Maid in Manhattan and When Harry Met Sally.
1. Leather Blazer + White Tee + Beret
Style Notes: I'm just a girl, standing in front of a computer screen dying to re-create this look. The beret, the glasses, the leather blazer: It’s all so good and all so relevant right now.
2. Tunic Dress + Roll-Neck Knit
Style Notes: This look is screaming "bookstore-owner chic.” Though, even if that’s not your vocation, this outfit formula would work for any industry. The roll-neck-and-tunic pairing is understated yet polished.
3. Contrast-Collar Dress + Handbag
Is it possible to discuss ’90s movie fashion without mentioning Clueless? As if! Dionne’s contrast-collar dress and mini handbag feel very 2021. Just lose the knee-high socks, and you've got yourself a look.
4. Cable-Knit Jumper + Miniskirt + Patterned Tights
Style Notes: Each year, this picture is posted to Instagram feeds the world over heralding the start of "sweater season.” And while it might have become a bit of a cliché, you can’t deny the timeless nature of a cable-knit, miniskirt and tights.
5. Blazer + Print Dress + Knee-High Boots
Style Notes: Okay, this is not technically a ’90s romcom, but we couldn’t create a list of stylish fictional women of this decade without paying homage to Hilary Banks. The woman was a blazer aficionado, and I particularly love the way she’s paired a blazer here with a printed dress and knee-high boots.
6. White Coat + Shift Dress
Style Notes: In the eyes of my 6-year-old self, Parent Trap’s Elizabeth James was the epitome of chic. Evidently, my taste hasn’t changed too much, as her outfits feel just as stylish today. This white coat and beige shift dress would look elevated no matter the decade.
7. Tonal Outfit
Style Notes: Take me on a walk through Central Park wearing a borrowed outfit any day if the outfit looks like this. This is tonal dressing done right.
Next up, the biggest autumn/winter 2021 trends you need to know.
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Elegant Dressers Always Choose This Impractical Yet Chic Coat ColorJennifer Lopez is one of them.
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Jennifer Lopez Just Wore the $98 Jeans the Internet LovesShe must've read the reviews.
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8 Especially Chic Jennifer Lopez Outfits That Rely On Elevated BasicsShe has a good eye.
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J.Lo Carried a $10K+ Bag With the Anti-Trend Wardrobe Item I Never Spend More Than $100 On*Never.*
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Celebs in Their 50s Are Styling Jeans in an Anti-Casual Way, and I'm Here for ItDressed-up denim.
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Jennifer Lopez Just Wore the Most Relatable Anti-Trend Jeans-and-Boots OutfitWe love casual J.Lo.
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With Moana and Cabaret's Sally Bowles, Auliʻi Cravalho Gets to Do It AllThe actress returns to the character who started it all.
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J.Lo Just Debuted a New Way to Wear This "Boring" Blazer Trend That Feels So 2025BRB, I'm adding one to my cart.
