The first time I ever walked into a thrift store with the intent to actually buy something, I was twenty-two and broke as hell. My first “real” job interview was the next morning, and I needed a suit that wouldn’t make me look like I was wearing a borrowed costume. My budget was somewhere between laughable and nonexistent, which is how I found myself in a Goodwill on Chicago’s North Side at 6:45 PM on a Tuesday, digging through racks of discarded formal wear that smelled vaguely of mothballs and old cologne.
I must have tried on fifteen different jackets before I found it—a charcoal gray Brooks Brothers in what appeared to be nearly perfect condition. The pants were nowhere to be found, but the jacket fit like it had been made for me. Twenty-two bucks. I paired it with some dark navy trousers I already owned (a rookie mistake, but better than the alternative), polished my one pair of decent shoes, and somehow landed the job despite my mixed-up suit. The interviewer—a guy named Richard with immaculately tailored everything—actually complimented the jacket. “Brooks Brothers, right? Older model, maybe ’90s? Good find.”
I nearly choked on my water. That was the day I realized two things: people notice quality even if they can’t articulate why, and thrift stores are gold mines if you know what you’re doing.
Fast forward about a decade, and my apartment now contains more secondhand designer pieces than I’d care to admit to my financial advisor. That twenty-two dollar blazer kicked off what my ex-girlfriend called “an unhealthy obsession” and what I prefer to think of as “strategic wardrobe building.” I’ve since discovered that thrift store shopping isn’t just about saving money—though god knows I’ve done plenty of that—it’s about finding pieces with character, quality, and history that you literally cannot buy new anymore.
Last month, I found a Polo Ralph Lauren tweed sportcoat from the early ’90s when they were still making them with full canvassing and natural shoulders in the USA. The price? Thirty-five bucks. The same jacket new today would run you $900 and wouldn’t be half the quality. My best friend Trevor refuses to go thrifting with me anymore because, according to him, “watching you fondle old jackets and mutter about stitching for three hours isn’t my idea of a Saturday well spent.” His loss.
Look, I get it. Thrift shopping isn’t for everyone. There’s a certain… let’s call it an aroma that permeates most secondhand stores. The lighting is usually terrible. You’ll have to sort through endless racks of truly hideous clothing. And yeah, occasionally you’ll run into someone who’s having an animated conversation with an invisible friend by the housewares section. But for me, the hunt is half the fun. It’s like a treasure hunt where X marks the spot of a perfectly broken-in Alden loafer or a Brioni tie for less than you’d pay for lunch.
So, for those of you brave enough to dive into the world of high-end thrifting, here’s what I’ve learned from years of hunting down designer pieces that rich guys got tired of:
First—and this is non-negotiable—you need to know your labels. Not just the obvious ones like Ralph Lauren and Brooks Brothers, but the niche players too. Spend some time educating yourself about what the inside of a Zegna tag looks like versus a Zara knockoff. Learn to spot the difference between Alden and Aldo shoes at a glance. This research will save you from bringing home expensive-looking garbage.
One rainy Thursday, I found what I thought was a Burberry trench coat for $40. I was so excited I didn’t bother with my usual inspection ritual. Got it home, went to clean out the pockets and found a tag I’d missed—”Burberri” with an “i.” Couldn’t return it because I’d already removed the thrift store tags. My roommate Marcus still calls it my “Burberri adventure” and no, it wasn’t funny the first fifty times either.
Second, develop a circuit and hit it regularly. My personal rotation includes three Goodwills, two church thrift shops, a consignment store that doesn’t understand how to price menswear, and a Salvation Army near a wealthy suburb where finance guys dump last season’s impulse purchases. I visit at least one spot per week, usually on weekday evenings when they’re less crowded. Timing matters—ask the staff when they put out new merchandise and plan accordingly.
It was during one of these regular sweeps that I found my white whale: a perfectly preserved 1960s Oxxford suit in a charcoal sharkskin wool that makes modern suits look like they’re made from paper towels. The full story involves me sprinting across a parking lot to beat another shopper to the rack, but some details are better left untold. Just know I regret nothing.
Third—and this separates the amateurs from the pros—always, always check wealthy neighborhoods. The donation drop-offs near Gold Coast or Lincoln Park in Chicago, Upper East Side in New York, or Beverly Hills in LA? Absolute gold mines. Rich people clean out their closets too, and they’re a hell of a lot less likely to wear things until they fall apart. Some of my best finds have come from stores where bored housewives drop off their husbands’ barely-worn clothing because they “needed closet space for the new collection.”
My buddy Eric once found three Charvet dress shirts with the dry cleaning tags still attached at a Goodwill in Winnetka. Retail price would’ve been around $400 each. He paid $7.99 per shirt and looked liked he’d won the lottery the entire rest of the day.
Fourth, make friends with the staff. I’m on a first-name basis with Diane who runs the men’s section at my favorite Goodwill. She knows what I like and sometimes sets things aside. In exchange, I bring her coffee and don’t haggle on prices that are already ridiculous. This relationship has paid dividends—like the time she called me about a donation that had just come in: three pairs of Allen Edmonds, barely worn, in my exact size. The previous owner had died (a bit morbid, I know), and his son had dropped off his entire closet. I still wear those shoes at least weekly and silently thank both Diane and the unknown original owner.
Fifth, know when to splurge and when to walk away. That cashmere Loro Piana sweater with a tiny moth hole? Probably worth the $25 if you know a good tailor who can repair it invisibly. That Gucci shirt from 2003 with the massive logos all over it? Leave it for some fashion student’s ironic project. Buy quality, not labels, and certainly not trends that were questionable even when they were new.
I once left behind a genuine Versace silk shirt because it was a ’90s print so loud it would’ve made Elton John ask if I was feeling okay. My friend Marcus still hasn’t forgiven me—he’s convinced it would’ve been worth hundreds to the right vintage collector. Maybe he’s right, but I couldn’t in good conscience add it to my wardrobe, and I’m not in the business of reselling.
Sixth, learn basic alterations or make friends with a good tailor. Most of my thrifted pieces have been adjusted in some way. Sleeves shortened, waists taken in, buttons replaced. My tailor, Jun, has saved countless finds that were almost perfect. He charges me a bit less because I bring him regular business, and I occasionally bring him bottles of the Japanese whisky he likes. The cost of the item plus alterations is still usually about 10-20% of retail, and the result is clothing that fits better than anything you’d buy off the rack.
Case in point: I found a Cucinelli sport coat last year for $45. It needed the sleeves shortened and the waist taken in slightly—another $65 in alterations. So $110 all-in for a jacket that would have cost north of $3,000 new. And because the previous owner had already broken it in, it has a comfortable, lived-in quality that new clothing lacks.
Finally—and this is crucial—know what can’t be fixed. Shoulders on a suit jacket? Nearly impossible to alter well. Stains on silk? Forget about it. Heavy wear on shoe soles? Probably not worth resoling. Learn to spot these deal-breakers quickly so you don’t waste time falling in love with something that’s fundamentally flawed.
I made this mistake early on with a gorgeous pair of Crockett & Jones oxfords that had clearly been worn in the rain repeatedly without shoe trees. The leather was cracked in ways that no conditioner could resurrect. Sixty bucks wasted on shoes I couldn’t save. A painful lesson, but an effective one.
The real joy of thrift shopping isn’t just saving money—though finding a $2,000 blazer for less than the cost of two movie tickets never gets old. It’s about the stories. Every item has lived a life before it came to you. I have a Turnbull & Asser tuxedo shirt that still had the previous owner’s collar stays in it, monogrammed “ASW.” I sometimes wonder who ASW was, where he wore this shirt, what occasions it witnessed. There’s something almost poetic about giving these pieces a second life.
Not that I’m getting all sentimental about used clothing. But there’s a satisfaction in building a wardrobe of exceptional pieces that most people couldn’t afford at retail—not because you’re trying to front like you’re richer than you are, but because you’ve put in the time to learn what quality looks and feels like.
So next time you pass a thrift store and think “not for me,” maybe reconsider. That Goodwill in an unassuming strip mall might just have a piece of fashion history hanging on its racks, priced somewhere between a fancy coffee and a cheap dinner. And even if you walk out empty-handed, the education is free. Just don’t tell too many people about your favorite spots. I’m still mad at whoever wrote that viral TikTok about my church thrift store. Some treasures are better kept secret.
Leave a Reply