David, hey. This question is a lot of fun. Comin to you live... it's the class of 2005. I know your reunion isn’t ‘til next month, but it feels like the perfect time of year to be talking about reunions — no matter how old you get, there’s always a “back to school” feeling in the air in the fall. It’s invigorating. And it’s invigorating me… to help you find something to wear to this thing.
I’ve been to a Brandon High School reunion (we are mighty, we are fine, we’re the class of ’79) although Ann and I went back and forth about which one. She thought it was the 10-year, but I think it may have been 20. Anyway, I think I wore a pair of printed pants and a navy blazer, which doesn’t narrow it down much. Sounds like me in 1989, sounds like me in 1999, sounds like me in 2029, probably. But let’s kick it over to you and what you’re gonna wear.
So. You’re definitely going with a sport coat. No question. Especially if you’re going for sprezzatura. Y’all are adults now — even if you were all kids together — and you’re going to dress like adults to celebrate the occasion. A woven shirt, since it’s fall, but in the spring or summertime you could probably do a polo under your jacket. And then the jacket gives you some leeway on your bottom half: you can go as casual as jeans or 5-pockets, or as formal as dress trousers. On your feet: either boots or loafers… for some reason, lace-ups feel like they’re trying a little too hard at an event like this. A touch too formale. And then I could go either way on the tie. I'd wear one, personally, but I think it’s one of those things you gotta feel out when you get there. So that’s another role the sport coat plays… gives you a pocket to stash your tie in.
So that’s the rough formula. I pulled together some specific looks using what we’ve got on the floor right now, and kind of organized them by level of sprezz. On one end of the spectrum you’ve got a low-key, super quiet (but super elegant) look with a monk’s cloth jacket and grey trousers. The fun part is the shoes, which are made from wild boar skin (cinghiale.) Kind of an interesting fact if someone compliments you on them, but they’re not calling too much attention to themselves. And then on the other end of the spectrum is a look that really just goes for it: big-time color on the pants and big-time pattern on the jacket, but in a way that has some harmony to it. I think it's fantastic. And then a couple of in-between options: green pants and a soft glen plaid jacket to turn it up a notch, a larger-scale plaid coat and off-white corduroys to turn it up two notches.
If you’re having trouble figuring out which one speaks to you, maybe ask yourself this: Who am I excited to reconnect with at this thing? Will I be proud to talk to them in what I’m wearing? Will they remember who I am in what I’m wearing? And am I gonna feel like myself in what I’m wearing? Ideally the answer to those last three is YES. You want to look familiar, just subtly better… not like you’ve gone and totally made yourself over. For example, I’ll say this: no one at the BHS reunion blinked twice at my bandana pants. I may have been on the football team, but I wore some kooky stuff in high school. It’s great to get more stylish over the years, but a total 180 could weird people out... you know your audience. So, yeah, only you can decide if the 2025 you is wearing a windowpane jacket with purple cords... or if he’s going for something quieter. If in doubt, you can always keep it super simple and classic with a navy Ghost blazer and your favorite pants in your closet. That thing goes with nearly everything — a navy blazer is always right — but the unusual buttons give it a bit of interest. Second-look-type sprezz.
Anyway, I hope this was helpful. Thanks again for throwing this question into the ring. And have a great time. These things can be fun if you make them that way. And everything’s more fun when you like what you’re wearing. Cheers to the class of 2005.
