10 of the Best Clothing Items to Buy Used

A Discussion Around Smarter Secondhand Shopping

The opening of our new retail boutique sparked a conversation about secondhand shopping. In this little chat, John Bramaan and I touch on the various advantages of buying secondhand clothing instead of new.

We decided to make a list of best buys. As it turned out, the task proved more difficult than expected. While we did manage to settle on a definitive list of items, we didn’t always agree on what should be included and why. Read the discussion below and feel free to add your opinion in the comments.

JB – Clearly one of the main advantages of buying clothing used rather than new is always going to be the price. However, maybe we can start by discussing items that are not only cheaper, but also just better when secondhand. For example, I personally find most leather jackets quite ugly when they are too new and shiny. Instead a well broken-in leather jacket is a thing of real beauty.

RS – Absolutely. I feel that way about many leather goods really. Furniture, especially. A brand new Chesterfield sofa for example, has no personality compared to a well used version. That’s why so many brands apply treatments to give the leather a distressed or worn-in look.

JB  – Yeah, that’s a good example, perfection doesn’t suit leather. It needs to be lived in, develop character.

RS – Aside from that, here price really is a major consideration, as you can save a ton of money when buying a used leather jacket.

JB  – Right. In fact it really makes little sense to me why anyone would buy a leather jacket new. It’s one of the rare cases where you’re guaranteed to pay more for what is effectively an inferior product, in the sense that it won’t really look good until it’s broken in anyway. So why not just buy it secondhand in the first place: cheaper price and better looking product right from the off.

RS – Well, part of the problem is that they’re not so easy to find. The stylish ones must sell really fast in vintage stores and flea markets, so you’re often left with a lot of generic leather junk to browse. When something good turns up and it fits, you jump on it.

JB  – Yeah, that’s very true unfortunately. In fact maybe most people just don’t part with the really good ones in the first place.

RS – I think that denim, too, can be a better buy secondhand than new – especially the raw variety. It takes such a long time to break-in. So if you’re impatient and need a genuinely distressed pair, buying used is a good idea.

JB  – I’m less sure about denim: just from a hygiene point of view. I wouldn’t hesitate to buy a used denim jacket, but without wishing to dwell on this point for too long, jeans are worn pretty close to the body and, for many guys…well…rarely washed.

RS –  You’d definitely want to dry clean them or launder them in some way: that goes without saying. But if they’ve been properly cleaned, I see no problem.

JB – OK, then I think we can also add heavy cotton canvas workwear to the list. Particularly chore jackets. Like raw denim, heavy canvas can be really stiff when new, and it takes a while to adjust to the wearer’s body. But once it does, it’s a truly beautiful fabric. So whether we’re talking about genuine vintage workwear, or workwear-inspired pieces from contemporary brands such as Visvim, APC, or Undercover, these always look better to me when worn-in.

I have something of a fetish for the way that pockets on heavily used chore jackets and military-wear start to take on a much looser, more curved form over time. I’ve saved a photo somewhere of a shirt once owned by North Vietnamese leader Ho Chi Minh. Not because I have a secret passion for military history, but purely because the shirt has such nice saggy pockets. I wish you could get pockets looking like that on new items, but I don’t think any amount of clever cutting and stitching could replicate it.

RS – Maybe you can replicate the look if you keep a cigarette pack in your front pocket for several years. I wonder what Ho Chi Minh kept in these pockets?

JB – At a guess, his hands: it was like a workwear shirt with low front pockets.

RS – That makes sense. As long as the pocket corners are in good shape: they can start to fray over time. That look works well on jeans, but on canvas pieces it’s a deal breaker for me.

JB – I guess it depends on just how close the garment in question is to genuine workwear. On the real thing, I think that worn corners can look great. But I agree that fraying is less attractive on a garment that is more obviously just a fashion item, particularly one otherwise suited to more formal situations. Worse still if it’s at the collar tips.

That makes me think of military-wear vs military-inspired pieces. Buying militaria new makes little sense. And by this I mean things like reproductions of combat jackets produced by luxury fashion brands. Unless the design has been radically overhauled in some way, I’d rather just have the original – assuming you can find it. Given that it was essentially designed for crawling though the jungle on your face, rather than sipping cocktails in Paris, it will likely be much better made anyway.

RS – Maybe I’m more the type who would buy the designer reproduction. Yes, it’s not made for combat, but then it also fits better and the construction is a more practical everyday weight. I’ve heard that navy pea coats are a good secondhand buy, but can’t imagine finding a vintage peacoat that I’d really like to wear.

Also, we should note with the luxury remake that it’s not always a designer label borrowing looks from military designs. Some of these companies, like Schott and Burberry, were the original makers who produced military supplies. It only makes sense to modernize their classic pieces and continue selling them to us civilians.

JB  – This brings us to another theme I thought we should discuss. More and more brands have cut production standards in recent years. So even if well worn, a vintage product may well be of far superior quality to a more modern item. I mean, it seems that even for those brands that do want to make good products today, many of them struggle to source high quality fabrics, as very few truly excellent mills are still in business.

RS – Yeah, in my experience, Flannel shirts were better in the past. I recently got a high end (>$200) shirt as a gift. Nice fit and fabric, but the buttonholes all frayed within 3 months. That’s something that would never happen with a thrift store Pendleton shirt. It seems like after a garment has been around a decade, it’s more likely to last even longer. Like it has passed the endurance test.

JB  – I have pieces in my closet that I bought new almost 20 years ago now, and that I still wear regularly. I recently had the elastic replaced on one lightweight cotton shirt/jacket – as it had lost all stretchiness and resilience – but otherwise the piece still looks almost like new. The fabric is in amazing condition. I wonder how many of the products I’ve bought new in the last year will still be going strong in another 20?

What about suits? Unlike denim or workwear, I’m not sure that we could convincingly argue that a suit gets better for having been heavily worn, but its price certainly does. I think I wrote about this when we did the guide to buying secondhand suits online some months back: a lot of people are wary of buying a suit without trying it on first.

Given that fit is so important with a suit, this is entirely understandable. However it means that there are a lot of very nice suits out there, with many shoppers just too scared to buy them, thus pushing down the price. So if you know what you’re doing, you can pick up some amazing bargains in this department.

I’ve purchased several 1K+ suits online in near pristine condition for well under $200 – including a really nice Burberry wool flannel suit that was probably worn only once for a wedding.

RS – You’re right, when it comes to secondhand suits, it’s all about saving money. And you can save quite a lot of money. But we should really discuss which suits in particular are smart to buy used. Which style or brand or…fabric?

JB – Well, I’d say that if you’re looking for a heavier, traditional woolen suit, then this will almost certainly be better for being older. Whereas, for a suit in a really lightweight fabric – even if it’s wool –  I’d be more inclined to go new. In part this is because lighter fabrics will likely wear out much quicker, and therefore there might be less life left in a secondhand one, but also because it’s these kinds of fabrics that seem to have really evolved through technical innovation in recent years. For a more rustic, heavyweight winter number though, secondhand would be my preference.

How do you feel about footwear?

RS – I usually browse the shoes first in any secondhand store. Wingtip shoes, brogues – i.e. the classic gunboat – are always a great secondhand find. They don’t make these shoes like they used to. You buy a new pair today and they’re either ultra light by design, or mass produced with cheap materials. They’re becoming less common in vintage stores, but you can still track down a sturdy pair of Florsheim wingtips with a double leather sole.

JB – This kind of formal footwear is likely to have been well looked after too. Which makes me think of neckties as well: probably the single item I buy most often secondhand. There are just so many of them out there, and often in near-perfect condition. Many going for an absolute steal.

As long as you read the measurements and don’t end up with an enormous  ‘70s kipper tie, there’s actually minimal risk involved in buying used ties online. On top of which, you can often pay less for a hand-rolled silk tie from an artisanal manufacturer than for a factory-produced one from a mediocre brand – purely because the former is lightly used. At that point it makes very little sense to me to buy new.

RS – I agree it’s easy to find nice used ties online, but shopping isn’t as simple as reading measurements. I like to see and touch the silk, and feel the overall weight of the tie. Some people ruin their ties with dry cleaning and pressing, and you can’t see that in a photo.

Regardless, the secondhand market is ripe with deals because of the general necktie surplus. The world could stop manufacturing ties for a year or three and we – the tie wearing types – would be just fine. People just tend to buy ties, hang them in the closet and then forget about them.

JB – But that seems like a good thing to me, rather than negative. Or are you saying that even secondhand ties aren’t such a great buy because, as with new ties, inevitably most of them will never get worn either?  Thus making them a bad deal.

RS – Exactly.

JB – OK, but I don’t think that makes ties an inherently bad buy. But rather just underlines the fact that we shouldn’t buy things we don’t need, or won’t have opportunity to wear. Ties or otherwise.

If you genuinely make use of ties, then it makes little economic sense to purchase them new when there’s so much choice secondhand. But of course, getting a bargain on something you’ll never wear is pointless.

RS – I’m guilty of over-buying myself. Then I always end up reaching for the black knit Brooks tie instead of the other more eccentric or hard-to-match ties.

JB – My fail-safe ties are just as likely to be eccentric secondhand purchases. In fact, if I had to choose just one single tie to take with me, I would go for an extrovertly-patterned, dark green, 1970s number from an obscure, and now defunct, Italian brand that I bought on eBay. Counterintuitively, it looks great with almost everything I own.

OK, so what does our list contain so far?

RS – We’ve got Military stuff, Wingtips, Flannel Shirts, Leather Jackets, Workwear, Winter Suits…and maybe Neckties. What else? Anything missing?

JB – What about pieces from retired or deceased designers? It can often be worth going out of your way to track down certain specific labels from a few years ago. The quality or look of clothes from a brand can change quite suddenly. Either because they switched manufacturer, or – perhaps more commonly – because the designer or creative director left, or even died.

Faconnable is an excellent example of this: although they are getting on a little now, Albert Goldberg-era Facconable items are well worth hunting out. And clearly anyone who’s a genuine fan of Martin Margiela or Alexander McQueen would want to go for pieces that these two designers actually had a hand in creating – rather than merely something with their names sewn in by an investment company with rights to the moniker. Miyashita-designed Number (N)ine would be another good example of this.

RS – Yeah, suppose you found the fashion designer that perfectly matched your sense of style, and then she died. It’s odd to watch another designer step into their shoes and attempt to continue under the house name. The aesthetic you love may or may not be reflected in future collections. So you might consider buying up more of the past season’s collections.

But of course, if your designer of choice was a big star like Versace, McQueen or Kate Spade, then some of those signature pieces are going to increase in value. So I’m not sure this qualifies as a smart secondhand score. It depends on where you shop, and when – relative to the designers passing. Sales of Kate Spade bags for example, were trending after the designer’s death. So in my opinion you might wait a few months to shop rather than competing with other fans reacting to news.

JB – True, but my point about buying pieces by deceased or departed designers wasn’t so much that it offers an economic advantage over buying new, but rather that if you really want, say, a Martin Margiela-designed product, buying secondhand is simply the only way you will be able to do so now. In this case, cost is irrelevant. Despite the label, the new product is not actually designed by Margiela. And if that’s important to you, then buying secondhand is the only option.

RS – OK, yeah, it doesn’t make economic sense anyway, so pay more if you must. I mentioned Kate Spade because of the recent news that resale sites reported huge search traffic spikes for Kate Spade items after the designer’s passing. But the designer herself wasn’t involved with the brand anymore, she sold it years ago. So when a designer dies and becomes the subject of massive publicity, you have to compete with people who may in fact be learning about the brand for the first time.

Like when David Bowie died, suddenly there were all these hip people interested in David Bowie and hosting Bowie themed art openings, cover shows etc. As fans mourn or celebrate a life, they generate awareness and thereby new fans.

JB – Yeah, the Bowie example is a good one. As you say, a big part of it’s simply the fact that this musician – or designer – perhaps just hadn’t really come up on your radar all that much prior to their death. Then all the critical acclaim on their passing makes you curious.

Going off on a different topic, how about trench coats? They don’t change in style much; they tend not to wear out; they are widely available and fairly priced; and they were well made before, and aren’t likely to be any better made now.

RS – Yes, secondhand trench coats tend to be of really high quality. The fit has changed though, with the older coats being slightly longer with a more relaxed cut. Previously it was expected for a man to wear a suit under his trench, but now that’s not necessarily the norm.

JB – A trench coat is now more likely to be worn over a t-shirt than a suit.

RS – Right, but if you size down, or perhaps do some alterations, you could add a great trench coat to your wardrobe for less than 200 bucks. Compare that to 1-2k for a new trench from Aquascutum or Burberry.

JB – This highlights the fact that, when you start to go a little further back in time with vintage items, in order to get a truly wearable item, some dedication and involvement is often necessary on the part of the buyer.

With older secondhand suits for example, you’re unlikely to get a very fashionable fit unless you have access to a reliable alterations tailor. You also need sufficient knowledge and confidence to know what alterations to request in the first place.

From this point of view, buying more recent models of secondhand designer-wear is a much safer bet, as the cut and fit will already be contemporary. As it happens though, the last few seasons have really seen the length of coats descend, and the oversized look is really big right now, so all those formerly old-fashioned vintage Burberry trenches are suddenly back on trend again as things come full circle.

For me, a lot of the fun and creativity in dressing well lies in mixing up items from a variety of different sources: lightly used designer menswear from consignment stores; dirt cheap flea market finds; new pieces from contemporary labels; even adapting modern workwear and military items. Basically whatever works.

Well, I guess some items are here by more popular consensus than others, but what follows is our final list of the 10 best men’s clothing items to buy used.

01. Military Gear

02. Wingtips

03. Flannel Shirts

04. Leather Jackets

05. Workwear

06. Winter Suits

07. Neckties

08. Denim

09. Pieces from retired or lost designers

10. Trenchcoats

What do you think? Have we missed any bargains? What would be your secondhand menswear shopping tips? We would love to hear some recommendations from readers.