Y2K Fashion Trends You'll Actually Want to Wear in 2026

Let me start by saying that I have never really let go of a lot of my pieces from the aughts. I’ve been a perpetual fan of combat boots, beanies, cardigans, statement jewelry, and oversized hoodies since high school. I fully embrace the preppy Y2K vibes that are on the Mui Mui runway, Tory Burch 2026 Spring/Summer runway and Paul Smith. I’m going to focus on a few trends that I think are versatile and will be wearable for a long time.

Sporty & Preppy Polos

J. Crew, Tory Burch, Mui Mui, and KBB by Kahlana (for Target) polo shirts

These shirts have been a staple in my closet for decades. A stripped or two tone knit jersey polo is easy to style with a cargo skirt, shorts, or jeans. I love the oversized stripes and remember rocking Johnny collar polo shirts with oversized men’s pants. At the time most of my clothes were thrifted from the men’s section. These tops come in every color variety you can imagine, so you can go bold or stay monochromatic.

  • Mui Mui Long Sleeve Polo, $ 1,550 on MuiMui.com

  • J. Crew Boatneck Rugby Shirt, $52 on J.Crew.com

  • Mui Mui White Johnny Collar Polo, $ 1,690 on MuiMui.com

  • Tory Burch Lavender and Brown Johnny Collar Polo, $280 on Toryburch.com

  • Tory Burch Little Grumps Cotton Polo, $180 on Toryburch.com

  • KBB by KAHLANA for Target Polo Shirt, $45 at Target (Sold out) It may still be available at some Targets but it is no longer available on their website.

Cargo Skirts

I used to wear the full length cargo skirts that had a million zippers, pockets big enough you could fit a small dog in, and drawstrings to add ruching on the sides. I’m now opting for “less is more” with a shorter type of cargo skirt that may not have any pockets or only a few, but have fun accents like metal loops, built-in belts, or an asymmetrical hem. These are a few that I could imagine being worn with a polo, tank top, or a baby tee.

Crochet Hats & Small Purses

When I saw that these colorful and fun crochet bucket hats and bags were making a comeback, I was so excited. These statement pieces scream beach vibes and just need some oversized sunnies to complete the look. I love all the variety of materials too – the raffia with crochet details on these cute summer bags is perfect for a weekend trip. I’m still a fan of the original Kangol Bermuda bucket hats too, of course!

Ties & Scarves

Collecting vintage ties and scarfs at thrift stores and resale shops is definitely what I recommend to create your one-of-a-kind looks. A favorites of mine is a vintage John Galliano scarf with a bold floral pattern and the Gothic magenta lettering with his name. These types of prints are personal depending on your tastes, but here are a few with Americana vibes, tweed and silk ties for a menswear inspired look, and a scarf top in a beautiful watercolor pattern.

Juanita FralinY2K Fashion, Preppy rugby shirts, checked shorts, beanie hats, cardigans, combat boots, hoodies, lace tank tops, braided belts