Guess ’90s-Inspired Festival Season Outfits

If there’s any time to stock up on ’90s basics, it’s during festival season . . . and if there’s any brand to satisfy customers looking for an affordable price point, it’s Guess. While there are plenty of over-the-top Coachella looks floating around TikTok — consisting of strappy bikini tops, voluminous hair extensions, and several pounds of body chains — some celebrities are making the case for a minimalist wardrobe this year.

From Hailey Bieber in her little slip dress and jet-black sunglasses to Kendall Jenner in rolled denim cutoffs, a white ribbed tank, and baseball cap, it’s clear that sometimes less is more in the desert (or anywhere there’s a music festival).

Chalk it up to renewed interest in Carolyn Bessette Kennedy’s style, or perhaps we were all on the same wavelength, but senior style director Jessica Andrews and I felt that same influence. We selected pieces from Guess’s Festival edit not just for the weekend, but for the long term. Our shoulder bags, embellished with Guess’s iconic hardware, scream summer in their own ways, be it the dopamine hit of marigold or the raffia texture. And Jess’s suede cowboy boots are clearly appropriate for all seasons.

Another detail we both appreciated from our selections? The functionality. My jeans were incredibly comfortable without feeling stiff — the type you’re totally OK to walk miles in — and Jess’s bomber jacket kept her warm during the inevitable temperature dip at night.

Ahead, see how we styled our festival outfits using Guess essentials that feel both luxe and classic enough to be relevant next year, too.

Guess Festival Season Essentials