How to Wear a Vest in 2025 (Plus One Look That’s Best Left in 2007)

The biggest difference between the 2025 version of vests as shirts and the 2007 version is that now we’re opting for much looser silhouettes. They don’t need to be totally oversized or super long, but you should feel like you’ve got enough room to maybe layer a cotton tee underneath and that you’ve got full range of motion in the hips. P.S. This applies to the pieces you wear with your vest too—leave the skinny jeans behind and opt instead for wide-leg trousers, A-line skirts or casual track pants.

Speaking of skirts, a midi skirt is a wonderfully chic and modern way to dress up a vest in 2025. It doesn’t much matter if you prefer a ‘90s straight up-and-down silhouette, boho tiers or a classic A line, all strike a feminine balance to the more masculine tailoring of the vest to create a gorgeous combination.

Typically suit vests have a V neckline to show off the button-up underneath, but if you instead choose a vest that has a higher crew neckline it instantly feels more like a shirt and less like an additional jacket-type layer. The best versions of this that I’ve seen tend to go past the hips and flare out a bit from the waist to help balance that high neck, rather than going straight down. This makes them incredibly easy to pair with high-waist trousers or skirts, but you could also opt for a lower rise for a peek of midriff that’s not quite as bold as a full crop top.

Don’t overthink it. Take whatever vest you’ve got and layer it over a pair of modern jeans (i.e. something with a slightly looser leg) to build a simple base that can stand on its own. Then you can use accessories to zhuzh things up in whatever way you like. Maybe you want to go more preppy with some ballet flats, a top handle bag and a Blair Waldorf-approved headband. Or you could go for a boho vibe with some colorful espadrilles, a slouchy tote and some floral earrings. Once you have a solid base down, the options truly are endless.

Whether you’re replacing your trousers with a pair of matching tailored shorts or denim Bermudas, the swap instantly helps to tone down the overt “office ready” vibes of a button-up vest. This is especially true if you add in some casual accessories like flip flops or a boho leather bag instead of opting for more polished pieces. As for the length of your shorts, longer silhouettes will ultimately serve you better here. Micro mini shorts run the risk of looking like you work as a cocktail waitress at a gentleman’s club, which is perfectly fine it that is indeed your day job, but not really the look most of us are going for when meeting with friends for brunch.

I love a good comeback as much as the next fashionista, but wearing all the resurging Y2K trends at once is almost guaranteed to leave you looking like you’re headed to a costume party. If you’re going to bring back the slim-fitting suit vest, swap those cropped skinny jeans for a wide-leg or barrel-leg style and replace those rosette brooches with a colorful statement earring instead.