A vintage shopping day in New York

Friday, May 3rd 2024
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Recently myself, photographer Alex Natt and Carl and Oliver from Rubato (above) spent a day vintage shopping in New York. It was a lot of fun, and also I think interesting for those that are fairly new to vintage, or can find the process frustrating. 

We all ended up buying something but not that much, and rarely what we set out for. Carl was not expecting to pick up a Ralph Lauren Purple Label jacket, for example, and would never have put it on a shopping list at the beginning of the day. But when he found one in beautiful wool and silk - at a good price and a perfect fit (below) - he still ended up getting it. 

To me this reflects the breadth of opportunity with vintage. For you’re not just shopping one season but dozens of them, from different eras, with different silhouettes and a greater range of materials. We hadn’t ever seen this cloth before and as RL materials are usually exclusive, it was always likely to be unusual. 

Serendipity like this is a big attraction of vintage shopping. You're more likely to be taken by surprise, and the clothes you're looking at won’t be ones you’ve already seen online, or in that season’s advertising and all over social media.  

My purchase was similarly unexpected. 

I’ve always had a weakness for suede jackets - bombers, overshirts and blazers. But I’ve never owned a western-style suede jacket, and instinctively thought it would be too unusual for me. 

When we visited Front General, Alex pointed out one in a roughout-suede hanging on the wall (always dangerous) and I tried it on. The cut really worked, and the heavy suede was beautiful - rugged and thick, with a shape that had been moulded by many years of wear. 

Of course, other brands sell modern versions and I might have seen one there (eg RRL or Buck Mason). But I wouldn’t have had the same open-minded approach. For me at least, vintage engenders this receptive attitude, ready to try anything and be inspired. And accept you might walk away empty-handed as well.

We tried on a lot of things we didn't buy, and wouldn't necessarily have seen in a regular shop. Above, for example, Carl is trying on an old Polo polo coat and I'm wearing a scarlet duffle coat, also Ralph Lauren. 

That red rather overwhelmed me, particularly in the long length of those old Ralph ones - but it did mean I knew my size in case I ever saw one on eBay, and I now have a search set up. 

In fact, something else I tried worked out very well in that way. The tassel loafers I featured recently on PS were a model I originally saw at Crowley’s but were just a size too big. I looked on eBay, and luckily found a pair in the right size. 

For what it's worth, I would never do that with something that was available in a store. It will always be more expensive of course, but the owner deserves the margin for sorting through mountains of stuff, paying the rent to display the best things, and then being there for me to try on and buy. 

Perhaps that's a luxury of having the money do so, but I do think people should take responsibility for their actions in that way if they have the money. If they don’t, the shops will disappear.

Oliver's experience was a little different, in that he didn't find anything inspiring, but he had been looking for some US Army chinos for a long time, and found a decent pair at 10ft Single (above).

It’s easy to feel like this kind of military clothing is everywhere, and so vintage is actually not that variable. It’s always the same field jackets, varsity jackets and denim jackets. But often that means you just need to seek out a different kind of vintage shop - like Crowley, which has such a huge range of Ralph Lauren and similarly inspired clothing. The popularity of vintage means more of these shops or sites are springing up. 

Plus eBay has more variety than you could possibly hope for. Lucas has been on a deep dive into Giorgio Armani for the past couple of years, and now has a crazy knowledge of all the labels, periods and materials. Perhaps he'll open his own Armani-and-similar-eighties-tailoring shop some day. 

Alex, the fourth member of that group, is also a good example of different tastes. He's more into modern vintage and knows all the history of the outdoor brands like Eddie Bauer and North Face. 

It's great shopping with a friend like that, as they'll point out and tell you about pieces you'd never consider. He didn't buy anything the day we all went, but he had bought a US parka earlier in the week, and that was the budget blown.

Vintage is not for everyone. I’ve spoken to quite a few readers about this in recent years, and it's not suited to those that aren't into clothes enough to talk about them and research them. Perhaps like someone who enjoys cooking, but isn't going to spend the time talking to their local butcher or travelling to a farmers market. 

I'm still very much a novice, but in the past five years I've bought many of my favourite pieces of clothing vintage, and found it incredibly interesting and enjoyable. I hope this first-hand experience helps explain a little where the joy comes from. 

Rubato are in London for their next trunk show from May 23-25, being hosted by Taillour at their atelier.

For more on vintage, see:

Shops in New York visited:

  • Stock Vintage
  • Church Street Surplus
  • Stella Dallas
  • 10ft Single
  • Sean Crowley
  • Front General
  • Rugged Road

Also recommended: Raggedy Threads

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May I ask why some of you are wearing masks in some of the photos, and not in others?


He’s got bad allergy I recall


Just curious How does someone else wearing a mask help his allergy?


Perhaps he’s allergic to uncovered faces.


Agree. It’s weird.

Lindsay McKee

I can’t bring myself to embrace vintage, be it clothing , watches or whatever.
For me, in buying something new, the thrill comes from being the original person to own the garment, watch or whatever.
However ROV, if I may call it as such, “Reproductions Of Vintage” would possibly be more up my alley.
Did you, for instance, not cover examples of this in various articles. I’ve forgotten who but I think that an article on those who provide Reproduction Vintage would make a very interesting article.
Who are the best people in London or Europe for ROV, if I may?

Lindsay McKee

Many thanks


&Sons and Co is another. They have a shop in Cheltenham and online.


Most of my outerwear, sweaters, jackets, etc., are vintage and the driving impulse is that I see it as a rescue mission. It’s a pity to see some beautiful item from the past just sit there on a rack, unworn, unappreciated… where would it end up if I didn’t grab it, take it home and care for it?


I agree with you about the reasons to buy new as opposed to used. I never understood why someone would want to buy someone else’s used items regardless the price. I think that I would feel like a poseur if I bought used items.


The idea of wearing a garment Steve McQueen Paul Newman prince of Wales opened would have a certain thrill even if no one else knew .maybe that’s part of it,the secret…


Just to have an idea: the price of the Purple Label jacket was under or above USD1,000 ?

Charlie P

Where should I visit in London for a similar experience?

Simon S

Do people still wear masks in New York? Seems so long ago I saw someone with a mask in Sweden outside of hospitals…


Hey Simon, I feel buying vintage especially online can be very tricky. I bought 3 pairs of wide khaki chinos which the measurements check out but they all had their quirks that made them all less than ideal (e.g. one tapered in an unexpected manner, another too tight around the sit, another looks too wide etc.).


Hi Simon. Just about to spend the morning at Portabello Market. Not quite the same, but you never know? As you say, go with an open mind, be prepared to walk away with nothing, but most of all have fun. If nothing else it broadens your knowledge and shopping in person enables you to connect with people.


Hi Simon – which stands are you referring to in Portobello? Also would you visit the shops?

Ronnie Pickering

I had a flat on Portobello for a while. 280 so up by the flyover. It was a bit ago – just as Golbourne Rd was starting to get exciting. I spent many a happy afternoon wandering around the antique market, the vintage stalls, the shops, the cafes, the pubs and the bars. There is some interesting stuff but I’m not sure there’s much to compare to the really world class shops in your sartorial guides. But I also think there’s a different kind of retail experience – one that’s more about a gentle wander with no real destinations in mind. I’d be interested in hearing more about those kinds of locales – interesting neighbourhoods with a good mix of menswear (vintage, new), other shops., cafes, bars, restaurants where a permanent style reader could spend a happy afternoon and evening.


Re. the Rubato trunk show – will the prices be the same as those UK customers have to pay on the website, which were recently increased substantially with the justification that the sale price now includes import duties, or will those additional costs be removed to reflect the fact that the goods are being sold to UK customers in the UK? Thanks.


Thanks for checking that Simon.

Lawrence S.

For comparison: Rubato’s prices appear to remain unchanged here in Germany. The only change I can discern is that shipping is now free of charge, regardless of how much you spend. So from my perspective, their new e-commerce partnership makes their garments (slightly) more affordable.


Having seen your write about tailoring for many years and recently a lot about vintage I’d love to know whether you buy from ‘high street’ retail ?

By ‘high street’ I don’t mean Rubato, Brycelands , Trunk Clothiers , Drakes etc.
(These being what I would then high-end high St retail .)

If so what do you buy ?

I’m just wondering because I don’t think you’ve written anything about that .


Thank you .
Please do write more when you come across quality high street retail .

And also independents on the high street or web .
It’s one of the ways my purchasing habits have changed learning about them in this blog .


Hi Simon,
Regardless of any other comments and my preferences, this looked a lovely day out. Browsing clothes, in knowledgeable interesting company. Very enjoyable I’m sure. You must love your job, in fact it may not even feel like job sometimes. Hope you had a pleasant New York lunch.




Hi Simon. That’s a great list of vintage stores in NYC (some of which I still need to visit). Two others I can suggest which have both B&M locations and online sales. The first is Wooden Sleepers, which I believe you wrote about a few years ago? It was originally located in Brooklyn but has since moved about 30 mins by train outside the city to a town called Crestwood. It’s a little more difficult to get to and visits are by appointment only, but the owner has a great eye for curation. Lots of military, workwear and outdoor pieces, most in excellent condition.

The 2nd one is a new discovery for me (it was actually my 13 year old son that led me there) called Vintage Planet. It has 5 stores mainly in suburban shopping malls of all places. The inventory is pretty expansive and not nearly as curated as some of the other shops, with a mix of sportswear, military, workwear and outdoor pieces from a broader range of brands and eras. But when I visited one of their stores I came across a few nice finds at very good prices. For example, a vintage Woolrich Mackinaw is around $250 to $300 at Wooden Sleepers while Vintage Planet has a very similar one for $75.00. Definitely requires more digging around online but there are good deals to be found.

And just in case anyone is wondering: I am not in any way affiliated with either of those stores. Just a lover of great vintage pieces. Cheers and have a nice weekend! John

Jamie Ward

The green jacket you’re wearing on the penultimate shot looks great on your Simon

J Crewless

Yeah, it’s hard to walk away from outerwear that’s caught one’s eye. I can’t do it either.

Nice article.


Be ready for the tipping point in your life, Simon, when clothes you find in “vintage” stores are clothes that were sold new when you were in your teens or twenties.


Ah… I wonder if the new-to-vintage process for clothes happens at a faster pace than in the past.
In the late eighties when I first began frequenting vintage stores, they sold stuff heavily from the ’30s, ’40s and ’50s. Some stores had a few rare pieces that were much earlier, a coat or varsity sweater from around 1900-1910. I guess when it was that old, clothing was still considered “vintage” while its furniture counterpart was “antique”.
Items from the ’60s looked too new still in the eighties, the stuff of yard sales or the back corners of home closets… or simply the stuff on the backs of passersby older than we were.


Say it ain’t so, Simon.

Tempus fugit.

J Crewless

Forgot to say that the suede jacket doesn’t even look broken in. Looks like a fine purchase.

Here in the US, clothes, even good quality ones are seen as disposable and discarded after a couple of wears with years or decades of life still left in them.

Haven’t bought anything new except for the usual stuff in decades, and enjoy wearing all of the pieces until no longer serviceable; which for some items could mean decades even they’re already 50-60 years old.


Hi Simon,
Great article! Did you happen to notice if any of these NYC stores had sections devoted to larger sizes? I love shopping vintage in person, but hard to find my size. Online is usually where I go, but I definitely enjoy the thrill of going in person. Thanks!


I wanted to visit Crowley so badly when I went to New York and then noticed, on a Monday three days before parting, that he only opens on Saturdays for a few hours. What a bummer!


Hi simon. An off topic question maybe you can help with. I commissioned my first bespoke suit a few months ago (largely because I was inspired by this site). When I had my first appointment I was a bit overwhelmed with the choices and didn’t reallly describe what I wanted very well. I fumbled through it using pictures on my phone but eventually trusted the tailor.
On the second fitting I realised that maybe the garment wasn’t going to be what I wanted exactly. But when I brought it up he sort of convinced me to stick with the ‘house’ silhouette.
I am about to go into to my third fitting and feeling like I have some buyers remorse because it seems to late now to be more assertive.
Mainly, after doing a lot more research on the terminology etc I want something with more drape and movement and I feel like the silhouette the cut is quite slim.
The commission is with a well know tailor that you have reviewed and was very expensive. I accept that I should have been clearer from the start and done more research but my question is, at the third fitting is it futile to try to get them to loosen up the garment a bit. And is that expected etc that a client can still ask for changes at every stage of the process within reason?
I read that bespoke tailors leave more fabric available in the cut for future amendments. Anyhow, hoping it’s not a totally lost cause as I want to be proud of my first tailored garment and wear it often. I just doing think I would with that slimmed down style they’ve created thus far.
Thanks for the advice.


Oh great. That’s a relief. I will communicate this to the tailor when I go for my next appointment. Thank you.


The RLPL blazer would have been made by Chester Barrie some time between 1998-2002…..the glory years of RLPL.

john kalell

Love your attitude regarding the honoring of the sweat, effort, and cost of maintaining retail space; and making the choice to purchase from a shop rather than tapping through eBay . Bravo!


Most vintage is shabby. You need to kiss a LOT of frogs and I don’t have the patience. I did find an amazing shearling coat in Brussels once for 35 euros. I buy a certain defunct brand on Ebay ( which I won’t even mention here as I don’t want to attract competition 🙂 ).

Christopher P.

Great post Simon! So glad you found something at Front General Store. I lived less than a 5 min walk from there for a decade and would go all the time. Since moving to Suburbia I don’t get there as often as I’d like but still try to 4-5x a year. It’s one of the better curated stores in NYC and while their vintage selection is fantastic and among the best in the city, I love that their stock is not exclusively vintage. Their accessories and jewelry are fantastic as well.