How to Kill It at Your Class Reunion

I graduated from Berkeley High School (Go Stags!) way back in 2004. That’s right, 10 years ago. Back when Janet Jackson and Justin Timberlake got nasty during the Super Bowl and nobody knew what an iPhone was. All that means is that my 10-year reunion is coming up soon, like in a few weeks. While I’m pretty confident and excited about my accomplishments over the past 10 years, no one at the reunion really cares about that stuff. They’ll be more interested in asking the important questions: Who shrunk miraculously like Jonah Hill? Who ballooned to sumo wrestler–like proportions? Which ugly duckling turned into Kate Moss?

I’d say as much as 80 percent of the interest in these things is how well has everyone aged. How does everyone look? And what you wear can really tell that story in a good way or a bad way. So, here’s a few tips on how to put the best version of you on display and make that old flame or crush rethink their adolescent decisions.

A navy suit is really the safest option. It requires very little commitment because it can be reused for just about any occasion. It would certainly be the most versatile use of your money. To help spice things up a bit, nix the white shirt and go for something a little less “business office-y,” like a patterned shirt. I like this one from Gant Rugger. It has a cool wave motif in the of-the-moment shade of indigo. Also, feel free to have some fun with the shoes and opt for the just-released Adidas x Pharrell Williams collaboration on the iconic Stan Smith sneakers. Done in all black and with the three stripes stripped, they’re very understated and sure to help bring things together seamlessly.

• JCrew Glen Plaid Wool Suit
• Clarks Leather Desert Boot

If you’re looking to spice things up a bit more, go for this glen-plaid number by J.Crew. Constructed from English wool, it’s sure to keep those fall winds at bay. With so much eye candy going on with the suit, it's best to keep the shirt and tie solid. For the shoes, go the unpredictable route and forgo the oxfords for a leather desert boot. It has the ruggedness of being a boot to go along with the English countryside origins of the suiting fabric, but exudes elegance due to the supple leather.

• Suit Supply Lazio Grey Stripe Suit

Last (but surely not least), even if the waistline hasn’t been kind to you over the years, there’s still something for you, too. Suit Supply is a fairly new brand (started in 2000, alhtough they didn’t begin to make real noise until recently), so they don’t offer separates yet. But their sizing goes up to a 50-inch chest and 44-inch waist. Your best bet is to go for a striped option. The vertical lines will help create the illusion of height, which will in turn help you appear slimmer. It has a notch lapel as opposed to the peak, which would only draw more attention to your broad chest. Speaking of which, skip the pocket square, which draws attention to your chest, too. And lastly, the fit is highly important. You want there to be zero break from the pant hem to the shoe to help maintain that vertical line, which—let’s say it together now—makes you look taller and slimmer. 

So, I've just given you three different ways to absolutely break necks at your high school reunion. Take your pick, keep your head held high, and knock 'em dead.

Edited by Felicity Rhode