I had just gotten back from a preliminary injunction hearing and was finishing my follow up notes to the client when Jordan waltzed into my office. A sense of deja vu overcame me.

“Jordan”, I asked, “didn’t you wear that suit yesterday?”

“Of course! I only have three suits, and the other two are at the dry cleaners. So this was my only option.” He seemed confused why I’d even ask such a silly question.

“You have three suits? You should be wearing a suit only once a week. You’re an attorney, have to wear a suit at least 5 days a week to the office, and you have only three suits?”

“Yeah. Why, how many do you have?” he asked, defensively crossing his arms.

“Well, I have 14 in my wardrobe right now. But that’s just my summer rotation. I’ve been too busy here at the office to switch out to fall rotation.”

I might as well have punched him in the gut. “14 suits? I have three suits and some ties my uncle gave me, and you have 14 suits in just your summer rotation? What a schmuck. Small wonder I hate you so much. You have some magic clothing expense account you failed to tell me about?”

“Well, Jordan, I actually have a secret to tell you about how I get my suits…”

 Here’s a secret: Much of my professional clothing is secondhand.

It’s true — I am a schmuck. Also true — as of today, I have 14 suits hanging in my wardrobe, including everything from Brooks Brothers, to Southwick, to Oxxford. I don’t remember exactly how many. How do I afford it? No, I don’t have either a trust fund or offshore accounts.

Answer: I shop smart. Many of my suits are like-new secondhand buys, picked up for pennies on the dollar.

There’s no shame in wearing secondhand clothing

So you’ve just graduated and are looking for that first job while trying to dodge Sallie Mae’s phone calls. Money might be a little tight. Or maybe you’re loaded, but are just not the type to pay $5,000.00 for a handmade bespoke suit. Come on!

Whether you’re a pauper or a miser, you can still afford to buy quality and look like a million bucks — you might just have to look outside the four walls of a traditional brick and mortar menswear store.

I’m a big fan of the theory that one should buy things that are made to last. Who cares whether someone else bought them first? Kind of like a used car, clothing loses a substantial amount of its initial value as soon as it’s off the lot — so you can save a lot when you buy used. But whether you use eBay & Etsy, troll thrift stores, or frequent higher-end consignment stores, you can often pick up some top-quality garments for a fraction of the original price.

Here are a few of my tips to scoring a great deal.

Know what brands are worth buying

Like most things, menswear varies in quality. Brands are an oft-used shortcut to help you gauge quality versus crap. But just because you’re heard of a brand before doesn’t mean they’re any good. If you’re at a thrift store and you see the following brands for a bargain, you’re on a roll:

  • Brooks Brothers
  • Polo Ralph Lauren
  • Corneliani
  • Oxxford
  • Southwick
  • Boss
  • Zegna
  • Alden (shoes)
  • Allen Edmonds (shoes)

These are fashion brands and generally not worth your time:

  • Kenneth Cole
  • DKNY
  • Calvin Klein
  • Joseph & Feiss
  • BCBG

Know Your Measurements

One thing that plagues many men is a real understanding of their size. (Here’s a hint: there’s more to it than just S/M/L/XL).

I’ve seen many guys who seem to subscribe to the idea that larger sizes are more manly, and as a result wear shirts, suits, and shoes that are way too big. (See. e.g., Paul Ryan, though he won’t do what I tell him).

Here’s a hint: wearing an oversized suit doesn’t make you look manly, it makes you look like Tom Hank’s character at the end of Big. You going to play chopsticks for your clients?

What complicates matters even further is that each brand seems to have its own idea as to how sizing works, so what might be a 44R in one brand might be a 46R in another. You can’t really trust labels.

If you can try clothes on in person, well, problem solved! You know right away whether it fits.

But if you’re buying online, you should know what your measurements are. Take the time to go to a local tailor (not a dry-cleaner), pony up a few bucks, and ask them to measure you properly.

If you’re so much of a cheapskate that you won’t even pay your local tailor a few bucks, here’s a comprehensive article from my pals at Art of Manliness that explains how to do it.

Once you’re all measured, and you find something you think might fit you, compare your actual measurements to any listed measurements online. If you don’t see measurements, ask!

Easy & Cheap Alterations

If the measurements on garment you’re looking at are different than your own, consider whether alterations are work worth it. For example, altering pants is generally cheap and easy — whether waist or length — so long as there’s sufficient material to do so. Shortening or lengthening a jacket’s sleeves is pretty easy too.

Tough & Expensive Alterations

Altering the shoulders, chest, or length of a suit jacket is major clothing surgery that will make buying used a useless endeavor if you’re trying to save money. There’s also a big chance that even after the alterations, the jacket won’t look quite right. You’re better off buying something that fits.

Know When to Stay Away

There’s a big allure to snagging a big-name item for cheap. Heck, the brag factor alone sometimes is tempting — “Yeah, I got this $5,000.00 suit for $100.00 off of eBay.” But if it fits for crap and looks like it’s straight out of the 80s, what’s the point?

Stay away if:

  • Fabric is damaged. This includes moth holes, stains, tears, repairs, etc. You’re not going to be able to fix it worth a damn.
  • Fabric is stained. I feel like this should go without saying, but sometimes it helps to state the obvious. Leave those shirts with mustard stains or ring around the collar on the hanger. Shout doesn’t always do it.
  • Fit isn’t right. It doesn’t matter if you picked up a top of the line suit made of rainbows and unicorn hair for only 10 bucks. If it’s too big or small, that’s all anyone will see. Fit is paramount.
  • You see the clothing item is polyester. Suits, shirts, ties — polyester is almost universally a bad idea.
  • It’s obviously dated. This rules out leisure-suits, 4×1 double-breasted suits, polyester anything.
  • It’s worn out. Shoes can be resoled. A loose seam can be repaired. Ties can be recrafted. But sometimes, even the highest quality items have seen betters days and are beyond feasible repair. Remember, the whole point of buying secondhand is to save money. If you buy a nice tie for $1.00, but have to spend another $40.00 cleaning and re-crafting it, it is worth it? Oe if you pick up shoes for $10, but have to resole them for $80.00, are you maybe better off just buying new?

Keep it Simple and Sedate


The rule I’ve been invoking throughout this entire series? Yeah, it still applies here. Leave that wacky-patterned suit on the shelf. Though if you find yourself a nice navy, charcoal, or sedate pinstripe suit, go for it.


Ties are often readily available at most thrift stores, often for as cheap as $0.50. Look for regimental stripes, solids, pin-dots, and other classic designs. Stick to better known brands. I’ve picked up Brooks Brothers, Ralph Lauren, Paul Stuart, and other quality makers’ ties — which look brand new and would have cost $50-100 each in a retail store — at my local thrift outlet for a pittance.

I know I’m not the only one who’s picked up a great second-hand deal. What’s the best thing you’ve found secondhand?

(photo: A photo of a gag one million dollar bill from Shutterstock)


  1. Stephen says:

    Interesting article (minus the infusion of politics).

  2. shg says:

    Two issues. First, polyester is never appropriate. You seem to offer just a tiny bit of wiggle room on that (“polyester is almost universally a bad idea”). No. No. No. Polyester is universally unacceptable. There is no wiggle room.

    Second, shoes. Shoes mold to a man’s feet from body heat and movement. Once they’ve been worn by one person, they are uniquely his. The internal molding will never be undone.

    Feet are personal. Each person’s is slightly different. And they form the basis for our ability to stand and move (the whole hip bone’s connected to the knee bone thing). Wear ill-fitting shoes, or shoes that have molded to another man’s feet, and expect terrible things to happen to your knees, hips and back. It may taken years before the mistake is realized, but it will happen.

    Buy new shoes. Makes they fit correctly (or better still, buy bespoke shoes). Never walk a mile in another man’s shoes, except metaphorically.

    • Sam Glover says:

      I bought a polyester blazer at one point, because I am sensitive to wool. It sucks. But cotton wrinkles too easily and wears out quickly, and nothing says Jersey Shore like silk. So I suffer with wool.

      • shg says:

        Cotton is fine for a summer suit, as is seersucker and linen, but it will wrinkle and it’s supposed to. Being able to pull off wrinkly isn’t for everyone. Some do better with irony.

        No one does better with poly.

  3. Hey Leo: Really interesting post with some good tips. A little funny too.
    Best to you.

  4. Dave S says:

    Leo, funniest post on Lawyerist yet. And, some useful info. Thanks.

  5. Andrew says:

    What is your opinion of tie bars/clips? Pocket squares?

    • Leo says:

      Tie bars are just fine. The simpler the better.

      Pocket squares are tough to do right. A white linen tv fold is generally ok for everything. But never wear a matchy-matchy tie/ps set.

  6. Molly says:

    Thank you, thank you, thank you for this article! I know nothing about men’s clothing, but I know plenty about women’s clothing (because I am one) and I’m sick to death of my husband’s cheap looking “sateen” poly shirts. Now I can point him to this article and say, “See? SEE? Real lawyers don’t wear polyester.” Great advice about Goodwill/eBay, too.

  7. Melanie Callender says:

    Best Finds Yet! Burberry Trench new, tags on-$25. Louie Vuitton “Belair” bag $20 no sign of use. How? Right place at the right time.

  8. I found it hard to believe when one of my friends told me that he had 18 suits in his wardrobe! I genuinely thought that he was exaggerating. And besides why would anyone need so many suits? But yeah, I don’t think there’s any harm in buying secondhand suits, especially when you’ve to buy so many of them!

    • Leo says:

      Ideally, you should wear a suit only once every 2-3 days. Assuming you have to wear one suit every work say, that’s at least 5 suits.

      And if you’re a fan of variety at all, or live in climates with both hot and cold seasons, it’s helpful to have different fabric colors, textures, and weights.

  9. Kevin says:

    I haven’t tried the used suits, but I have purchased Allen Edmonds dress shoes off of Ebay for years. Knowing the retail cost and patience are the keys to success. Also, make sure to view photos of the shoes without the shoe tree inserted in them, and look at the heels and soles for uneven wear. I have purchased several pair of both Grayson and Park Avenue that were like new for less than half the cost of new, and had many complements from people on those shoes.

    I agree about the comments on buying things that are too big. Regardless of what you think about him, take a look at the way Scott Pelly’s suits fit him. (CBS evening news)
    Absolute perfection!

  10. D. Macklin says:

    Liked your post. Things are a little different for women, but affordability and looking good is a matter of taking your time.

  11. LT says:

    What are your thoughts on the quality of Tommy Hilfiger, Perry Ellis, Bar III, and Alfani brands? Thanks

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