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. From Julia Roberts's leather-blazer-and-beret combo in Notting Hill to Meg Ryan’s bookstore-chic attire in You’ve Got Mail, I quickly discovered watching ’90s romcoms was more than just a tool for escapism—it was also a source of new (old) outfit inspiration.
Keep scrolling to discover the autumn outfit ideas I plan to copy from ’90s romcoms, from Parent Trap to Maid in Manhattan to 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.
Arket Oversized Leather Blazer (£290)
Monki Cat Eye Sunglasses (£10)
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.
M&S Collection Pure Merino Wool Roll Neck Jumper (£35)
White Stuff June Organic Cotton Pinafore Dress, Green (£55)
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.
Alessandra Rich Contrast-Collar Mini Dress (£1170)
Balenciaga Neo Classic City Nano Croc-Effect Leather Tote (£1190)
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.
Abercrombie and Fitch Cable Wedge Mockneck Sweater (£62)
Ted Baker Mini Leather Skirt (£175)
Heist The Chevron (£26)
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.
COS Oversize Fit Blazer (£135)
Mango Printed Ruched Dress (£50)
Arket Leather Over Knee Boots (£290)
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.
Max Mara Madame double-breasted wool and cashmere-blend coat (£2160)
Karen Millen Contrast Stitch Utility Belted Pencil Dress (£135)
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 a tonal outfit done right.
Mango Pocketed Wool Coat (£90)
Hobbs Merino Wool Roll Neck Jumper With Cashmere (£79)
Zara High-Waist Trousers (£28)
Next up, the biggest Autumn/Winter 2021 trends you need to know.
This article originally appeared on Who What Wear
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