Why I’ve Spent Twenty Years Hunting Quality Menswear in the Most Unlikely Places

You know, there's something deeply satisfying about walking into a boardroom wearing <a href="https://sartorialhim.com/i-dressed-entirely-from-walmart-for-a-week-and-got-more-compliments-than-ever/">a $3,000 Brioni suit</a> that cost me forty-seven dollars. Not because I'm trying to fool anyone – honestly, half the attorneys I work with couldn't tell Brioni from Jos. A. Bank anyway – but because I understand what I'm wearing in ways they don't. That jacket has history, craftsmanship, and a story that goes beyond whatever factory churned out their off-the-rack navy blazers.

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My relationship with secondhand clothing started out of necessity, not hobby. This was back in the late '90s when I was a junior associate making decent money but hemorrhaging it on student loans and Margaret's engagement ring. I needed professional clothes that wouldn't make me look like I was playing dress-up, but my clothing budget was… well, let's just say it was inadequate for the wardrobe my career demanded. A senior partner had made some pointed comments about "investment dressing," and I got the message loud and clear.

That's how I found myself in a Salvation Army on South Street one Saturday morning, feeling like I was committing some sort of professional crime. The whole place smelled like dust and old fabric, and I kept looking over my shoulder like one of my law school classmates might walk in. But necessity is a powerful motivator, and I started actually examining what was hanging on those racks.

What I discovered <a href="https://sartorialhim.com/the-30-wears-test-a-sustainable-approach-to-mens-fashion-decisions/">changed everything I thought I knew</a> about building a quality wardrobe.

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The first real find was a Brooks Brothers suit – navy pinstripe, probably from the '80s when they still made everything in the US with proper construction. Fifteen dollars for the jacket, ten for the trousers. I took it to my dry cleaner, had it pressed properly, and wore it to court the following week. The fit wasn't perfect, but the quality was unmistakable. Good wool holds its shape differently than cheap fabric. Hand-sewn buttonholes don't look like machine work. Details matter, and this suit had them.

That's when I realized something most men never figure out: the best-dressed guys aren't necessarily spending the most money. They're just better at recognizing quality when they see it, wherever they find it.

Over the past twenty years, I've developed what you might call a systematic approach to <a href="https://sartorialhim.com/classic-menswear-vs-modern-reality-what-still-works-today/">hunting down exceptional menswear</a> at fraction-of-retail prices. It started as economic pragmatism but became something more like… well, Margaret calls it an obsession. I prefer to think of it as applied expertise.

See, once you understand construction, fabric quality, and proper fit, you can spot worthwhile pieces anywhere. That includes estate sales in Rittenhouse Square, consignment shops in suburban strip malls, and yes, the occasional Goodwill. The location doesn't matter – quality construction is quality construction, whether you find it at Barneys or buried in a rack of polyester disasters.

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My best find came three years ago at a church rummage sale in Gladwyne. I almost didn't go – Margaret had dragged me along while she hunted for vintage jewelry. But I wandered over to their pathetic men's section just to kill time, and there it was: an Oxxford suit in charcoal wool that someone had clearly never worn. The tags were long gone, but the construction was unmistakable. Full canvas, hand-padded lapels, genuine horn buttons. Someone's father had probably ordered it bespoke in the '70s and never had occasion to wear it.

Twenty-five dollars. I actually felt guilty paying so little.

Here's what I've learned about finding quality pieces in unlikely places: you need to know what you're looking for before you start looking. Most people see "old suit" and keep walking. I see construction details, fabric weight, and maker's marks that tell me whether something is worth my time. It's pattern recognition developed over decades of wearing proper clothing professionally.

The hunt requires patience and a certain tolerance for… let's call them suboptimal shopping conditions. You'll spend hours sorting through racks of clothing that should have been thrown away years ago. The lighting is usually terrible, the organization is nonexistent, and you'll develop an intimate familiarity with the particular mustiness that pervades most secondhand shops. But occasionally – maybe once every twenty visits – you'll find something extraordinary.

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Location matters enormously. The best hunting grounds are near wealthy neighborhoods where people clean out their closets regularly. I've had tremendous luck at shops near the Main Line suburbs, places where finance executives and corporate lawyers donate clothing they've barely worn. These aren't desperate people selling possessions – they're affluent folks making space for new purchases.

My regular circuit includes half a dozen spots I visit monthly. There's a consignment shop in Wayne that gets excellent men's clothing but doesn't know how to price it properly. A Goodwill near King of Prussia that seems to receive donations from several high-end closets. An estate sale company that specializes in Main Line properties and occasionally has remarkable menswear.

I've gotten to know the people who run these places. Dorothy at the consignment shop calls me when something exceptional comes in. The estate sale folks know I'm interested in quality menswear and save me trips on sales that won't have anything worthwhile. These relationships matter – good pieces get snapped up quickly by people who know what they're looking at.

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The key is knowing what can be fixed and what can't. I'll buy a beautiful Hickey Freeman suit that needs sleeve shortening or waist suppression – those are straightforward alterations that any competent tailor can handle. But shoulder fit? That's nearly impossible to alter properly. Heavy wear on expensive shoes? Probably not worth the cost of resoling. Stains on silk ties? Forget about it.

My tailor, Roberto, has saved countless finds over the years. He understands that I'm not buying these pieces to flip them – I'm building a wardrobe of quality clothing that I'll wear for decades. He charges me fairly for alterations, and I bring him steady business. The cost of a thrift store suit plus <a href="https://sartorialhim.com/the-truth-about-custom-clothing-when-its-worth-it-and-when-its-not/">proper tailoring</a> is still usually less than 20% of retail, and the result fits better than anything off the rack.

Not everything works out. I've made my share of expensive mistakes over the years. A beautiful cashmere overcoat that turned out to have moth damage I hadn't spotted. A pair of Alden shoes with sole wear that made resoling impractical. A "Burberry" trench coat that turned out to be an obvious knockoff – embarrassing mistake that I should have caught immediately.

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But the successes far outweigh the failures. My closet now contains pieces I never could have afforded at retail: Huntsman sport coats, Charvet dress shirts, Church's shoes that have been resoled twice and still look exceptional. These aren't impulse purchases – they're <a href="https://sartorialhim.com/the-vintage-pieces-worth-hunting-for-and-the-ones-to-skip/">carefully chosen additions to a wardrobe</a> built around quality and longevity.

There's something appealing about wearing clothing with history. That Turnbull & Asser evening shirt I found at an estate sale? Someone wore it to important occasions, special dinners, memorable evenings. The previous owner clearly took care of it – proper cleaning, careful storage, quality collar stays still in place. Now it serves the same purpose in my wardrobe, carrying forward a tradition of proper formal dress.

Young attorneys sometimes ask where I find such well-made clothing. When I mention estate sales and consignment shops, they look at me like I suggested shopping in dumpsters. They'd rather buy mediocre new clothing than exceptional used pieces. Their loss, honestly. They'll spend $800 on a modern Brooks Brothers suit with fused construction when they could find a vintage canvassed version for $75 and have it tailored properly for another $100.

<a href="https://sartorialhim.com/the-fast-fashion-alternatives-that-dont-cost-much-more/" data-wpil-monitor-id="3">The economics alone should be compelling</a> – building a wardrobe of exceptional pieces at a fraction of retail cost. But there's more to it than saving money. There's the satisfaction of recognizing quality that others miss, of preserving well-made clothing that deserves continued wear, of understanding craftsmanship in ways that casual shoppers never will.

Margaret still thinks I spend too much time hunting through secondhand shops, but she's never complained about how I look in court or at firm events. The suits fit properly, the fabrics drape well, and the construction details communicate professional competence in ways that most men's clothing simply doesn't. That's worth a few hours monthly sorting through racks of discarded clothing.

Not everyone needs to build their wardrobe this way – if you can afford quality retail clothing and don't mind paying full price, more power to you. But for those willing to invest time instead of money, willing to learn about construction and quality, willing to hunt through imperfect retail environments for exceptional pieces, the rewards are substantial. You'll dress better than men spending ten times what you spend, and you'll understand your clothing in ways they never will.

Just don't tell too many people about your best sources. Good hunting grounds are scarce enough without additional competition from people who finally figured out where the quality clothing ends up.