A Decade Later, I’ve Returned 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, so-bad-it’s-good way. 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 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 at 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 over the top of 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 on to 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 too, there are tons of great men’s vests on the market right now, 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 share my tips on how to wear them.

The Minimal Vest

To start off, I decided to test out a clean, minimalist vest like all the top models are wearing. I was instantly drawn to the muted color and elongated silhouette of this Peter Do vest. I leaned into a neutral color palette, and paired it with a white tank and jeans, a black Bottega Veneta Cassette bag, and black Christian Louboutin boots. As someone who rarely does minimalism, this new outfit felt fresh and exciting to me—like it’s a more elegant version of myself. I’d definitely wear this to the office. Is baring one’s arms in a professional setting weird? Whatever, I work in fashion!

The Cozy Sweater Vest

For my second vest, I wanted to experiment with a more seasonally-appropriate vest. It’s cold out, after all! I love the red color of this knit Bode cardigan vest, and how it subtly ties in the front—not to mention it’s super cozy too. Once again, I found myself drawn to pairing it with a white tank top (might as well really go for showing off my muscle-less arms!), and then I finished it off with classic blue jeans, Gucci loafers, and my favorite Éliou charm necklace. For a more covered look, this could also be layered with a black turtleneck, or underneath a coat on the weekends.

The Going-Out Vest

Last but not least, I wanted to push myself to see if I could put together a vest look for the evening. When you’re grabbing drinks with friends, you may not think about reaching for a suit vest—but I was pleasantly surprised to see that it can be both cool and dressy. I love the subtle logo flex on this black Prada vest. I paired it with my favorite groovy Raf Simons turtleneck, Wrangler dress pants, a black By Far patent bag, and my trusty Louboutin heeled boots. I have to say, this was my favorite look of the bunch. My high school self would be proud of how far we’ve come. I’ve officially redeemed myself!