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If you’ve recently rewatched Whatever It Takes, chances are you weren’t just there for the adorable love story—you were also admiring the peak Y2K fashion. Released in 2000, the teen romantic comedy perfectly captures the turn-of-the-century aesthetic with slip dresses, baby tees, low-rise jeans, cargo pants, tiny handbags, and effortlessly cool prom looks that still inspire fashion lovers today.
Whether you’re recreating Maggie’s cool girl style, Ashley’s popular-girl wardrobe, or simply embracing early 2000s fashion, here’s every outfit I’ll be finding affordable lookalikes for.
Maggie’s Prom Dress
The movie’s most memorable fashion moment is Maggie’s dreamy prom dress. The gown features a simple slip silhouette that feels elegant rather than overdone—a perfect example of minimalist Y2K formalwear.
Ashley’s Light Blue Prom Look
Ashley opts for a glamorous blue prom ensemble that’s quintessential 2000.
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Everyday Y2K School Outfits
The casual wardrobe throughout Whatever It Takes is filled with pieces that have made a huge comeback.
You’ll want to recreate the look with:
- Baby tees
- Ribbed tank tops
- Low-rise jeans
- Cargo pants
- Denim mini skirts
- Platform sandals
- Chunky sneakers
- Tiny shoulder bags
Read More: John Tucker Must Die: How to Get the Y2K Style From the Cast
Cheerleader Style
Ashley and the cheer squad embody classic late-’90s and early-2000s high school fashion.
Look for:
- Pleated mini skirts
- Camis
- Tube tops
- Hair clips and butterfly accessories
Date Night Looks
The film also features plenty of simple, feminine outfits perfect for casual dates.
Ideas include:
- Floral slip dresses
- Cardigans
- Satin camis
- Platform sandals
- Mini handbags
Y2K Accessories That Complete the Look
No early 2000s outfit is complete without the accessories.
Shop for:
- Butterfly clips
- Stretch chokers
- Rhinestone jewelry
- Colored sunglasses
- Mini shoulder bags
- Platform flip-flops
- Jelly bracelets
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