I've Returned to My High School Obsession—Vests—After a Decade

I went through a major vest period in high school. In a Y2K, so-bad-it's-good way, not in a nice, minimal, Kendall Jenner–inspired way. At the time, many of the It ladies (such as Nicole Richie and Lindsay Lohan) were wearing suit vests with graphic shirts, and I wanted to get in on the trend. I recall going to our local mall and immediately going to Le Château, a now-defunct Canadian shop that specialized in prom outfitting for teenagers. A black button-up waistcoat and a cream button-up waistcoat with a white satin back were among the suit vests I purchased. I felt like a genuine star when I showed up at school in my new vests—paired with my favorite band tees, emo hair, and skinny jeans, of course.

Looking back, the vest-styling strategy was completely incorrect. I just looked like an angsty adolescent who stole a piece of his father's suit and wore it over his Evanescence shirts. Any visual proof of me at this period has left me scarred, to the point where I've avoided vests like the plague ever since. Vests have started to make a comeback on the street-style scene a decade later. Suit vests have been worn as shirts by trendy celebs like Kendall Jenner and Bella and Gigi Hadid this season, and they've been paired with wide pants and fancy bags. The vest is suddenly chilly again. Do I dare to go back and look at them again?

Never one to dismiss a trend, I chose to take on the challenge of wearing vests again this autumn. With ten years of design expertise dating back to high school, I was certain that I could make vest ensembles that were grown-up, elegant, and not trying too hard (meaning, not just with a graphic tee). Fortunately for me, there are plenty of wonderful men's vests on the market right now, in a variety of designs and materials, including comfortable knits, elegant leathers, and cool, techy textiles.

I put three vests to the test and provide my recommendations for how to wear them in the video below.