A decade later, I’m back to my high school obsession: vests

In high school, I went through a serious vest phase. Not in a cute, minimal, Kendall Jenner-inspired way, in a Y2K way, so bad it’s good. At the time, all the It girls (say, Nicole Richie or Lindsay Lohan) were wearing suit vests with graphic tees, and I wanted to replicate the style à la mode. I remember going to our local mall and headed straight for Le Château, a now-defunct Canadian retailer that essentially specialized in outfitting teenagers for their proms. I bought two suit vests: a buttoned black vest and a cream vest with a white satin back. Later I showed up at school in my new vests, paired with my favorite band t-shirts, emo hair, and skinny jeans of course, and I felt like a true celebrity.

Looking back, the vest style approach was completely wrong. I just looked like a distraught teenager who stole part of his father’s suit and threw it over his Evanescence shirts. I am scarred by any photographic evidence of me during this time period, so much so that I have avoided vests like the plague ever since. However, a decade later, I started to see vests making a comeback on 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 pants and designer bags. Suddenly the vest feels cool again. The question is: Do I dare to visit them again myself?

Never one of those to dismiss a trend, I decided to challenge myself to return to vests this fall season. Call it a redemptive style moment, but with 10 years of fashion experience since high school, I was convinced that I could create vest sets that were grown-up, sophisticated, and didn’t try too hard (that is, not just with a graphic tee. ). Luckily for me too, there are tons of great men’s vests on the market right now, and the new crop of vests comes in a variety of silhouettes and materials, including comfortable fabrics, stylish leathers, or modern, tech fabrics.

Below, I put three vests to the test and share my tips on how to wear them.

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