Cindy Crawford in the '90s Is the Blueprint—Here's How to Dress Like It's 1995

I don't know if it's the resurgence of slip dresses, the fact that everyone's wearing vintage Levi's again, or just pure nostalgia kicking in, but lately, every time I open my closet, I find myself wanting to dress like it's 1995—specifically Cindy Crawford in 1995. Her street style was the definition of laid-back glam, the kind of effortless, slightly sexy, and polished look that basically invented off-duty energy before it was a thing.
The best part? You don't have to spend hours digging through vintage shops (unless you want to) to re-create it. Ahead, I'm breaking down the key pieces you need to channel peak Cindy Crawford vibes this summer, from the perfect straight-leg jeans to the simple tanks and leather jackets that still feel just as fresh now as they did back then. Time travel isn't possible (yet), but dressing like it is very much within reach.
Blazer + Belt + Jeans
Style Notes: The most noteworthy Cindy Crawford looks from the '90s involve spotting her dodging cameras to get through airport security. This is one of the most timeless outfit combinations of all time. It never fails.
Tennis Necklace + Lace Dress
Style Notes: If this archival '90s dress was still available for purchase, I'd go try it on right now. Lace has had a major moment on the runways the past few seasons, and this dress is proof that it's timeless.
Bandage Dress + Matching Heels
Style Notes: Bandage dresses are having a moment right now with Hervé Léger and House of CB highlighting classic styles. It's a look that will never not be sleek.
Pendant Necklace + Black Maxi Dress
Style Notes: Oh, how I love a good pendant. It's yet another piece that is having a comeback, and it's so effortlessly and well styled on Crawford. Add this statement jewelry item to any LBD and you'll win best dressed.
Burgundy Dress
Style Notes: Some might think you need supermodel proportions to pull this look off, but actually, a knit maxi or midi dress will appear flattering and elongating on all different figures.
Blue Jeans + Leather Blazer
Style Notes: If this image wasn't time-stamped to the '90s, I would have sworn this was Kaia Gerber. Straight-leg blue jeans and a leather blazer are a foolproof outfit combination Crawford's daughter also relies upon regularly.
Cream Miniskirt + Black Tee
Style Notes: If this isn't the definition of "effortlessly chic," I'm not sure what is. Here, Crawford pairs a casual mini with a plain tee for the ultimate easy event ensemble.
Floral Skirt + Sweater
Style Notes: I'm pretty sure I wore this exact outfit over the weekend. That is how timeless it is. A floral slip skirt and crewneck sweater will never go out of style.
Silk Skirt + Jeans
Style Notes: You can never go wrong with an all-black ensemble. Crawford adds interest to the look here by playing with texture, opting to pair a silky shirt with jeans.
White T-Shirt + Sunglasses
Style Notes: Here's yet another airport outfit that proves all you need is the really good basics. You likely already own almost all the items you need to wear this outfit and look incredibly chic in it. If there's one thing I've learned from Crawford, it's not to overcomplicate things.
Orange Dress + Crewneck Sweater
Style Notes: An extra layer always brings something fresh to a classic look. Tying a sweater around your shoulders is so Crawford coded.
Hat + Corset
Style Notes: Try combining preppy and edgy pieces to tell an interesting story with your look. I love how the preppy cotton poplin top and pillbox hat look with a sharp corset.

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.
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