The Second Button – Exploring Men’s Vintage and Style

“I never really paid much attention to my style until after law school, and even then, I just wanted to learn the basics so I didn’t make a fool of myself. I looked online but didn’t find any easy answers. So I kept digging, until, one day, I found myself in love.

I started secondhand shopping out of necessity. After law school I had a mountain of student debt. So I would watch and lowball luxeswap auctions, which definitely helped me learn and explore a variety of aesthetics. And inevitably, while you learn to thrift better, you learn what the good vintage is.

And learning in person has helped me thrift better online. And so has writing about it all.

wool flannel suit

Ralph Lauren suit

wool flannel suit

My favorite vintage find is definitely this wool flannel suit from Ralph Lauren. It’s transformable; it can be buttoned at the lowest button or the middle button, and it looks good both ways. I didn’t realize that when I ordered it, I thought it was just a 6x2, but I think it looks better at the 1. Naturally, in my excitement, I wrote a whole article about it.

Online vintage from brands like Ralph Lauren, Levis, or milsurp. There’s enough of it out there that, even though everybody knows what the good pieces are, a lot of it is still very cheap. Now, there are exceptions. Ralph Lauren Polo Coats and 1950s Levis are not cheap. But Ralph Lauren Andrews and older Levis 517s are. Start with a great pair of pants or a few. Good pants hold up and are not too tricky to size.

camelhair coat

Brooks Brothers coat

pink men's cashmere sweater

camelhair coat

I learned much faster about secondhand once I found Alfargo’s Marketplace, usually my favorite place to thrift in person. Curated enough that I can almost always find a treasure, but most sellers there are very reasonable with pricing. It’s a great place to get a deal without having to go back at the right time every week, and I’ve made a lot of great friends there. I still meet new people there and have great, deep conversations about clothing.

My camelhair polo coat is definitely a highlight and bought at Alfargo’s. Brooks Brothers Golden Fleece, pure camelhair, a true luxury to wear. And my friend Shane at Alfargo’s gave me quite a deal on it. Maybe a tenth of what you’d pay for a Polo Ralph Lauren polo coat on eBay these days.

cashmere overcoat

Loro Piana cashmere

gray men’s cardigan

cashmere overcoat

Shane also sold me this cashmere overcoat at my first Alfargo’s (the second one ever), and I love it. It’s long and has a dramatic drape, and it’s incredibly soft, pure Loro Piana cashmere. The best way to get a great overcoat is to be friends with Shane.

Luciano Barbera

men’s navy blazer

Luciano Barbera

For the longest time, I didn’t have a great navy blazer. A friend showed me this one on eBay, from Luciano Barbera. The measurements seemed about right, the cut looked pretty nice, and it had patch pockets, which are rare for a DB. It was only $100 shipped, which is a fantastic price for the brand. So I bought it. And it didn’t need any tailoring. Now, obviously, I don’t mind tailoring my clothes, but there’s a certain serendipity in thrifting and finding a piece that fits you just right as is. It feels right.

vintage denim western shir

brown corduroy trousers

Dickies western shirt

vintage denim western shir

I spent more on this vintage denim western shirt than I care to admit, but I don’t regret it. It’s from Dickies’ Vaquero label, and it’s been worn to the point of being impossibly soft. That’s the charm of good denim, but I usually don’t wear denim hard enough to get there. But this shirt is there. It has a huge collar and fantastic details, too.

Guayabera

pink men’s shorts

men’s embroidered shirt

Guayabera

This is a weird one, but this gigantic, polyester-blend Guayabera just hits. I never would have thought to buy it online. It’s way “too big” for me, and the polyester content would usually turn me away very fast. But in person, I just needed it. I didn’t even realize it was a guayabera when I bought it. Instead of pleats, the front has a floral design in rows, exactly where the pleats should be. The buttons are in all the right places, And it just moves nicely. I love it.

I think of my style as eclectic. I like to experiment with different things. People describe my style relative to their own; they will say I’m formal, or casual, or modern, or old-fashioned.

grey flannel trousers

Oxxford

grey flannel trousers

I love these flannel trousers from Oxxford. They’re incredibly soft ’fawnskin’ flannel, and the perfect shade of gray. They keep a crease brilliantly–I’ve never had to iron them–and although they look like a straight cut, they’re actually cut with a very subtle flare. They’re slimmer than my average pair of pants, but they are just so clean.

I definitely get a fair bit of inspiration from Aime Leon Dore-type styling, but also from friends I’ve met at menswear events in the city, or friends I’ve found online. Most of them are into vintage or ivy aesthetics, so I might wear those a little more often, but I’m always trying to explore other aesthetics, I really just love clothes.

oxford button-down

Brooks Brothers Makers

oxford button-down

This oxford cloth button-down shirt once belonged to men’s style writer G. Bruce Boyer. It’s a dark red reverse stripe from Brooks Brothers Makers. He sold it through luxeswap on eBay, and it was sort of exciting when he listed a big chunk of his wardrobe through them. It’s light, it has a great collar roll, and it fits me perfectly. Very happy with it.

I really love golden era tailoring–the 30s and 40s–but then a sort of 50s-style casual aesthetic, and also some 70s styles when I’m feeling dramatic.

And I think there’s a lot to love in the modern day. I think Alessandro Michele, Dries Van Noten, and Steven Stokey Daley are fantastic. Still, I also have a list of bespoke tailoring houses that inspire me, including The Anthology, Maximillian Mogg, and Taillour.

men's linen pants

men’s short sleeve button up

Andrews pants men's

men's linen pants

Finally, and I’ll cheat a little bit here, my linen-blend Andrew pants. I bought both pairs on eBay, Like I mentioned, these are plentiful, they’re not expensive or hard to find. And they’re a wonderful cut. They come in linen, corduroy, chino... They have a wide variety of cuts, the Hammond is similar with reverse pleats instead of forward pleats. And... Yeah, I need another pair. Maybe black, maybe brown. We’ll see.”

The Second Button
@the.second.button