Dressed-up New Yorkers: The view from the pop-up

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Our New York pop-up (now in its second year) brings in an interesting range of people - more, perhaps, than London. 

There’s Guy, who came last time too, an old-school New Yorker in bespoke, red socks and Warren Edwards loafers; Duncan, the knitwear designer at RRL, in a tweed coat and workwear; and James, wearing a hoodie, big jeans and high-tops, but who was keen to try the Donegal coat.

It’s a real mix, and to an extent that reflects New York as a whole. There are more people in more unusual clothing - or just more clothing full stop - more of the time. Western gear goes unnoticed, as does hyper fashion. You see groups going out on the Lower East Side with everyone dressed to the nines: guys with long hair, vests, pearls; girls around Dimes Square parade in both big gowns and skinny leather. 

At the other end of the spectrum, I was taken for a lovely dinner by Paolo Martorano and Tom Mastronardi on the Friday night at Porter House, up on Columbus Circle. It reminded me how much New Yorkers dress up for dining like this. Everyone in that restaurant had made an effort, and the vast majority of men were in tailoring. It may have been mostly sports jackets, most without ties, but all were dressed up and tailoring was the obvious conduit to do it. 

It was heartening, as were the conversations we had every day in the shop. 

The space was split across two levels - Rubato and Seiji McCarthy downstairs, myself and Fred upstairs. Fred and I had lots of conversations with readers about how they wear tailoring today, and there was a real interest in casual textures, in big silhouettes, mixing genres. 

Downstairs, Rubato was going down a storm - their smart/casual mix perfect for all the men that said no one wears a suit at the office anymore, but they still want to look good. Equally, among the PS products the most popular were pieces like the Rider’s Raincoat and Cashmere Rugby, specifically because they could bring smart and formal. 

Two readers came in wearing the Rugby during the pop-up, and one was doing so with sweatpants and trainers, the other with suit trousers and loafers; both looked great. 

There was really only one day off during the week, what with setting up the shop and then packing up. But we used that to good affect, touring the vintage shops as a group, seeing the new expanded Front General space that had just opened, and visiting Rugged Road for the first time. 

I’ll do a separate piece on that later, as I thought it was interesting what all of us set out to find that day, and what we actually came back with. 

I’ll also do an updated New York shopping guide: I’m gradually trying to update those when I’ve revisited somewhere, and New York is next along with London. There’s also a new one on Berlin coming soon. 

Meanwhile, the photos in this piece are from the opening party, on the Wednesday night. Jake Mueser got a keg, which worked well: I reckon we’re more of a keg brand than a whisky-and-cigars outfit anyway. And lots of friends came by. 

Thank you to Jake, Chase, Matt and Jonas for helping us throughout the trip, with support and recommendations and many heavy boxes. Thank you to David and Emilie for their support, to Michael and John, and the lovely staff at the National Arts Club. 

Thank you mostly, precious PS readers, for coming and talking and sharing. I have to say my favourite time was the Saturday afternoon, when there were always several kids running around the top floor (families on the Saturday are the best) and I spent a good while entertaining them while their fathers tried on clothes and their mothers gave advice. There’s nothing like playing with other people’s kids when you miss your own. 

See you all next year. 

The London pop-up is being held at 19 Savile Row from November 8th to 11th. Details here

I am wearing my Taillour brown chalkstripe suit with a black Anthology T-shirt. Still in two minds about this with a crewneck - post on that little quandary sometime soon.

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Lindsay McKee

Oh Simon, you say you’re in a quandary about a crewneck worn under your lovely suit.
Look at Smedleys crewneck offerings. They have a very dark Orion Green or charcoal if that works with dark brown. I’ll leave that with you.

Lindsay McKee

I understand.
I will be interested to see your updated city guides when they come out and the new one on Berlin.
The corduroy suit in the B&W photo above looks very nice.
Would needle cord look smarter still, albeit in a casual way?


Really not a fan of the collarless look on you, especially with that outfit.

Your slim build and longer neck is exaggerated by that look, to the point where it doesn’t look very flattering. It also seems a bit off with a t-shirt with a fairly dressed up suit in (i think) flanell. It looks incoherent – if you wore a t-shirt with a spring/summer material it might make practical sense.

It’s still doesn’t look terrible – being tall and slim and wearing a well-cut suit pretty much ensures that you’re one of the better dressed people in the room regardless. It’s just that I don’t think the crew neck contributes anything to the look: it will always look better with a collar.

Completely unrelated, I have thought the Stockholm guide is way due for an update. Would you accept a collaborator on it? 🙂


This is sooo much fun event! Congratulations Simon and PS Team! I don’t spot Manish though. Surprisingly!


Haha! Thanks Amit!

I was there in spirit for sure 😊


Looks like a very nice week! The chalk stripe suit also does seem much more brown in this lighting than in the original article.


Hello Simon,
Have you ever considered doing a pop-up in Paris ? I would love the opportunity to try on PS items and brands such as Rubato, which are hard to find in France.
Congratulations on the pop-up and best regards,

Tim G

Hi Simon,

Long time listener, first time caller, as they say on US talk radio. I missed the NY pop up last year, but was doubly lucky this year in that I was not traveling and that the event was a reasonable walk from my office. I came during the opening night cocktail hour and it was buzzing. I spent a fair bit of time with the guys from Rubato who were generous with their advice and kind enough to let me try on multiple pairs of jeans and trousers (I ended up with the ecru denim you’ve written about). I was also able try on the PS Overcoat, which was great, once finding my right size. I actually had a couple randomly come over to say how great the coat looked on me. So, a nice complement on your work.

I did stop by to give you a quick hello and thanks, not wanting to really interrupt a long conversation you were having with another gentleman. You were very kind, though, in thanking me for coming.

This morning, I was surprised to see that I ended up appearing in this post! That’s me in the 2nd photo, with my back to the camera… blue/white jacket & filson bag.

Cheers on a successful event. I hope to see you again next year.


That jacket actually caught my eye. Where is it from?


Great to hear you were impressed by the sartorial offering in NYC. It’s fun to live vicariously through your observations. I must be wrong, but I thought that space above J Mueser is where FE Castleberry was? Maybe he’s floor above. I haven’t been for a couple of years.


New Yorker here. IMO a solid crewneck under that striped suit is still not quite enough. Besides the turtleneck or polo neck options in solids, another option might be a patterned woven or knit shirt. I’ve seen more Italians do this, but you, as an Englishman, have a lot of Liberty print heritage to explore, for example. The trick as always is finding the right balance of pattern style, colorway, and format size. What helps me is thinking of what patterns might have migrated from neck ties.


Simon- was the double breasted herringbone coat that was featured in some of the photos of the pop-up earlier in the week an example is the PS coat that’s coming this winter? Sorry if that’s spoiling a surprise, I’m looking for a new coat! Thanks.


Hi Simon,
Congratulations, the pop-up looks like it was a great time, hope to make it out for the next one. I have a slightly unserious question: can you expand on why you feel PS is more of a keg brand than a whisky and cigars one?
I can definitely see how the whisky and cigar associations might feel a little elitist and #menswear but was curious about the keg aspect. Either way it’s refreshing to see people in style who appear to be so down to earth and normal.


Always been fascinated by why sartorial culture as you put it pulls in those old ‘gentlemen’ hobbies like the cigars, & whiskey, sometimes eating steaks & other such activities Lol How did that happen Simon?

Paul H

Congrats, sounds and looks like a great event. I hope to be able to join one in the future.

I vote collar with the brown chalk stripe if taking suggestions Simon!


Do a pop up in Los Angeles!




Thank you, a nice Friday read. Can you give some hints on what to expect from the Berlin shopping guide? Really looking forward to it!


Looking forward to that, as well! It’s going to be interesting to see what you come up with – with Berlin being so obesssed with street style. I lived there for a few years and tayloring has never been much on display. But maybe that has changed.


Ups, “tayloring”. Too much Taylor Swift all around 😀

Tim J

Hey Simon,
Looks like a great venue and event. Do you happen to have dates in mind for London 2024 pop-up events as I’m likely to be visiting in mid-May?
That aside, I know you’re a little self-conscious about not wearing a collar under your tailoring (we all have our things), but I happen to think the t-shirt or crewneck knit under tailoring looks great and think you more than get away with it. In fact, it’s probably a great way of extending the life of tailoring beyond the office or formal occasion given the increasing casualisation of our daily lives.
I like the combination of black under the brown jacket too. Just go for it Simon!


Hi Simon,
These pop ups will remain as a great idea! I also think that the kind of ethnographic observation you made about new yorkers should be kept in your mind all along the next ones.
As to your outfit, a fine black roll neck could perfectly work too. You would then have to take into account – as already premissed in your choice – the occasion, the level of formality of the actual social envionment while being stylish!
For sure, it is not easy to find a good compromise when one is really aware that there would be a need to make the right one!


A very nice article that shows some very good thoughts about how men dress so totaly different. Which sweatpants do go well with the polo ? That sounds an interesting style.


I think you need to get over to the West Coast next time. Not that far after NYC. Remember, you have a loyal readership in SF/LA! And we have better weather…:)

Thomas Mastronardi

Might be too obvious an option, but I’ll often tuck a discrete scarf — discretely — into a crewneck. Having something that extends over the collar of my jacket seems to add a bit of visual balance as well as elevate the whole business for me.


Scarves (silk) also provide a layer of warmth in winter. I love them, I collect them. Now need to learn to tie them properly.

Thomas Mastronardi

Might be of some use, BB (but for me, more so with a crewneck rather than a shirt)…


I really like it when a man takes care of himself. He can dress nicely and attract women’s attention with his style


That’s the main objective Jack!


Time for a Sydney pop up; take advantage of our lovely summer here =P


Hello Simon. You mention RRL. As I sit here wearing an RRL cardigan, I’d really appreciate it if one day you found space for a piece on some of the more subtle (but not bland) clothing from RRL and how you would incorporate them into your workwear attire. I know you have covered RRL previously but it’s always good to hear more 👍


Nice to see the PS-meister having a ball in NY. Well deserved.


Hi Simon,

It was great meeting you at the pop up store and was really happy to get to try on the items in person! I went there with my wife with me wearing a supple brown suede jacket.
I was looking specifically for the Indulgent Shawl Cardigan and thankfully you let me try on that grey in small that fit beautifully. When are you going to have them again back in stock? Specifically the navy one. They are such wonderful pieces and would love to get one for this season.



Wish I could have made it, looks really cool, guess next year


Disappointing experience with Rubato. They have poor customer service and don’t appear to adhere to their returns policy – I have found it impossible to return any items ordered online as they don’t reply to you reply email despite emailing them numerous times. You’ve all been warned!


Dear Teddy,
Our apologies for your experience. Please email [email protected] with your inquiries and put “Permanent Style” in the headline and I will deal with it personally.
Kind regards,
Oliver – Rubato


Dear Teddy,
We’re still waiting on your email and would like to help you with any questions you may have.
Please get in touch with me and i’ll help you asap.
Kind regards,
Oliver – Rubato


Such a pleasure meeting you and the other menswear professionals. Clientele were very open and pleasant sharing thoughts. Wonderful atmosphere and cozy Manhattan neighborhood. My day trip on this occasion was a track meet with errands in Brooklyn, Midtown, Soho, etc. But wow, visiting your Pop-Up was the best part of the trip.