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