In high school, I went through a serious vest phase. Not in a cute, minimal, Kendall Jenner-inspired way—in a Y2K, so-bad-it’s-good way. At the time, all the It girls (say, Nicole Richie or Lindsay Lohan) were wearing suiting vests with graphic tees, and I wanted to replicate the à la mode look. I remember going to our local mall and heading straight to Le Château, a now-defunct Canadian retailer that essentially specialized in outfitting teens for their proms. I bought two suit vests: a black button-up waistcoat, and a cream button-up waistcoat with a white satin back. I later showed up to school in my new vests—paired with my favorite band tees, emo hair, and skinny jeans, of course—and I felt like a true celebrity.
Looking back, the vest styling approach was all wrong. I simply looked like an angsty teen who stole part of his dad’s suit and threw it overtop his Evanescence tees. I’m scarred by any photographic evidence of me during this time period—so much so that I’ve avoided vests like the plague ever since. However, a decade later, I’ve begun seeing vests come back onto the street style scene. This season, stylish stars like Kendall Jenner and Bella and Gigi Hadid have been wearing suit vests as tops, and pairing them with baggy trousers and designer bags. Suddenly, the vest feels cool again. The question is: Do I dare to revisit them myself?
Never being one to discount a trend, I decided to challenge myself to make a return to vests this fall season. Call it a redemptive styling moment, but with 10 years of fashion experience since high school, I was convinced I could create vest outfits that were grown-up, sophisticated, and not trying too hard (meaning, not just with a graphic tee). Lucky for me, there are tons of great men’s vests on the market right now, too, and the new crop of vests come in a range of silhouettes and materials including cozy knits, sleek leathers, or cool, techy fabrics.
Below, I put three vests to the test, and shared my tips for how to wear them.