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Jeff Hilliard is Director of Limited Editions at Hodinkee, the watch magazine/empire in New York. But he used to work at The Armoury, until 2017, and then did two years at Mr Porter. So while not strictly working in menswear today, he is certainly menswear adjacent. 

This makes him different to the kinds of readers we normally feature, but I think in an interesting way. How do people in an industry like watches - which is driven by many similar ideas of aesthetics and craft - tend to dress? I’ve been thinking about this as I bump up against industries like interiors and architecture recently too. 

Jeff is also just a great guy, very laid back, and I’ve always liked his perspective on clothing. So it was fun chewing over things like maturing style, or how we consciously play with the effect clothes have on people around us. 


Outfit 1:

  • Jacket: Made to measure by Ring Jacket
  • Trousers: Bespoke by Ambrosi 
  • Rollneck: William Lockie
  • Loafers: Made to order by Spigola
  • Sunglasses: Celine
  • Watch: Merci LMM-01 ‘Nationale’

Hey Jeff. So what’s the dress code like for you now, at Hodinkee? Is it anything like Mr Porter, or your days at The Armoury?

Well I still wear a lot of tailoring, just because it’s what I like. I wore ties less when I was at Mr Porter, but I was still in tailoring 90% of the time. I was one of the few people that was - in an office of 130 people - but the dress code was just, look nice, look good. You were in a place that’s about clothes, so everyone dressed well but had their own style. 

And you weren’t customer facing right?

No. We’d have events a few times a year that we hosted, but even then there was no dress code - the events were for VIP clients, and they’d just expect us to have a view on clothes, to have a style, rather than dress a particular way. In fact, the majority of staff at Mr Porter were personal shoppers in some way, so having style but also a broad awareness was essential. 

And at Hodinkee?

There are more people in tailoring definitely, maybe 10% or 20%, but my boss or I will be the only ones wearing a suit or tie - it’s mostly separates. I think the fact that I still wear tailoring so much shows how much of my personality is rooted in it. 

You were working in the office full time at this point?

Yes this was before Covid. During lockdown I got more into a sweater-and-jeans routine - I couldn’t wear sweats, that would make me feel like I hadn’t got up. But actually, the thing I realised after lockdown, when I started dressing up again, was how slim I used to have everything cut. 

And I hate skinny suits, mine were never that close-fitting. But everyone just got used to being more relaxed, and I’ve started wearing fuller fits as a result. I think that was a positive to come out of lockdown - in tailoring you get so used to thinking this is the one way, the only way to wear something, but clothing isn’t like that.

When does this suit date from? 

This is an old Ring Jacket, with trousers from Ambrosi. But even though it’s a fairly bold pattern, I think it reflects how I wear tailoring mostly these days: there’s no pocket square, no suspenders, no extraneous detail; everything’s a lot simpler. 

Is that preference for simplicity related to lockdown, or does it pre-date that?

I think it’s a general trend over time: dressing more simply, taking pleasure in things like textures or silhouettes. People say this happens with most people that collect things, clothes or watches or anything. Over time they become simpler, maybe more refined.

But the sunglasses are fairly punchy?

Yes, I guess maybe sunglasses are different because they’re practical, everyone has them. These are actually women’s ones from Celine - I tried a pair that my girlfriend had and really liked them. They’re slightly ‘cat eye’ in shape, but it’s subtle. They just look like a fairly big, chunky frame. 

If you look back at the guys we admire, from the 30s to the 50s, they often expressed themselves with accessories rather than the rest of their clothes. The suits would be plain, but they’d have interesting gloves maybe; Cary Grant sometimes wore these big sunglasses.


Outfit 2:

  • Jacket: Bespoke by Sartoria Corcos
  • Trousers: Bespoke by Ambrosi
  • Knit: Rubato
  • Shoes: Michael model from Paraboot
  • Watch: Merci LMM-01 ‘Nationale’

Do you have many things by Corcos?

No, this is my first, but I’m having anything new made by him now. I was so impressed by his technique. I particularly appreciate a good fit on the back of the neck, and I think only him and Liverano have got that right - and Corcos first time. 

I wouldn’t get rid of many of my other things though. Those from Liverano, from Panico. I have some pretty wild things from Panico, just big everywhere - one DB has lapels that shoot off the shoulders. It’s for when you just want to say ‘screw you’.

Have you always had your trousers made by Ambrosi?

Yes ever since the Armoury days. I always have the same model, the same cuffs, same waistband. And the fit is always perfect. These days I just send Salva the cloths I want and wait to receive them, no fitting or anything required. 

I’m pretty unusual with my suits also, like that first outfit, in that I’d have the trousers made by Ambrosi, even if the jacket was by someone like Ring Jacket. I’d get Salva to buy the cloth and make the trousers, then I’d give the extra cloth personally to Ring. One of the advantages of working in a menswear store.

I guess this is all pretty classic menswear except the shoes. 

Yeah the Michael has become pretty fashionable lately, though I’ve had mine for five years or more. I think they reflect my urge to always play around with things, not just to do the normal and expected. Maybe that’s a result of being exposed to so much clothing over the years as well - it can make you a little restless. 

And the sweater over the shoulders has its own associations - I guess it’s seen the same way in New York as it would be in London?

You’re still going to look like a rich asshole if that’s what you mean! The knit is from Rubato and I like how those guys wear them, but I’m aware there will always be connotations. When we were changing for this shoot I came out of the shop and a bunch of workmen on the street started jeering!

I like playing with that kind of thing though - again when you’ve been around clothes a long time, you’re very aware of the effect different things have, but just because something stands out, or has negative associations, it doesn’t mean you stop wearing it. Sometimes you enjoy playing with those effects; other days you don’t. 


Outfit 3:

  • Coat: Bespoke by Tailor Caid
  • Knitted shirt: Stoffa
  • Knitted cardigan: Stoffa
  • Trousers: Carhartt
  • Cap: Smithsonian
  • Shoes: Paraboot
  • Watch: Rolex 124060 Submariner
  • Sunglasses: Nackymade

So my eye immediately goes to the layered knits here - are they both Stoffa?

Yes I got them both recently from Nick [Ragosta, Stoffa], and for a bit I wasn’t sure how to wear the walnut one underneath. I think you’ve written about this - that the weight makes it a little light for a knit, but it’s also quite soft and thick for a shirt. 

I decided to wear it just like I would a regular polo, so under a cardigan like this, and if it were tucked in I don’t think you’d notice much difference from a regular polo until you got close. It’s too layers of cashmere though, so it is pretty warm.

I like the Tailor Caid coat, is that typical of his designs?

It’s pretty much what he does, like you can see the multiple seams on the bottom hem and he does a lot of herringbones. But some of the design was actually modeled after an image I had, - not that old, maybe the 2000s. 

The coat had this great, quite pointed peak, and a separation between the lapel and notch, almost like a fish mouth. He’s a great designer, so it’s easy to work with him on ideas like that. And it’s one of those things no one else will probably notice. The half-cuff is like that too. 

This outfit is most similar to how I dress day to day. It’s casual but there’s always a bit of tailoring. 

Are you a Yankees fan?

No, I’m from Chicago so this is kind of sacrilegious! I was at the Smithsonian a few years ago and saw this wool cap, and it was so nice, it’s worn in really well too, bent and beaten up in a different way to how a cotton one would be.Something about it works better with tailoring than a regular baseball cap as well.

The shoes are a little weird, like the other Paraboots in a way; it’s their take on a camp moc. I got them at CHCM - Sweetu [Patel] has such a great range, he’s my go-to when I want to step a little outside my comfort, find something different. 

They came with two sets of laces - leather laces by default, but also this set that I swapped them for, with the little cinch on the top. I regularly get asked what’s going on there. Though if I’m completely honest I like them because I hate tying shoes as well. You’ll see most of the shoes I wear don’t have laces because I’m just lazy. 

Cheers Jeff, and nice to see at the New York pop-up. Hopefully see you again later this year. 

Thanks Simon, you too. 

Photography: Christopher Fenimore

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The Corcos is amazing. Great style. Elegant but yet modern/young!

Jeff H

This is actually exactly how I would describe him and the reason that I started using him. Seeing him tonight actually for a few fittings in New York!


Hi, a follow-up question, if I may – what is it in the cut that makes the jacket elegant yet modern? Would appreciate your thoughts as the sweater obscures most of the jacket . Many thanks in advance!

Jeff H

It’s true, my sweater covers a bit of the core parts of the jacket, but you can go to the Corcos instagram where there are plenty of photos.

So, this is just how I feel, but the Florentine style of jacket I always found quite rustic and old school. The large and extended shoulders, the overall roundness, the square collar, the lack of extraneous detailing. At a glance, they can look a little bit like a work jacket or the casual sportcoats worn in the country at the turn of the century. This is always why I was drawn to them. Liverano felt different than everything out there, same with Seminara (who Kotaro studied under) and Marinaro. It’s always just resonated with me. But if I had one gripe with them, it’s that sometimes, they felt a little too old school.

This is where I think Kotaro makes his mark. His jackets retains that overall feeling (the roundness, the broad shoulders, the simplicity, the hallmark Florentine collar and no dart) but with slight tweaks. The lapels are a bit longer and the buttoning point is lower. He often recommends no vents. There is a slight curve to the breast pocket. Everything is just a tiny bit…sexier? Maybe sleeker is the better word. These are all small details but when you add them up they result in a house style that I think just looks so incredibly polished. Not to mention, Kotaro is such an incredibly skilled fitter, cutter, and tailor/maker.


Thanks, Jeff, very insightful answer!

Lindsay McKee

Nice to hear Sartoria Corcos mentioned in this article.
What I find striking are the style of the lapels and it would be nice to hear more about this guy, better still a commission and style breakdown report in the future Simon.


What is the colour of Rubato (fawn or ecru)?


Perhaps worth an article on Rubato’s colour palette and how you can choose between the subtle differences? That would be great!


I love Carhartt trousers. Together with Vans Authentic are the two items from mass market which should be considered a must in a perfect wardrobe.


Completely with you on Carhartt trousers. I have so many pairs.


I had a hard time believing those were Carhart – any idea what style they are?

Jeff H

They are the Ruck – no longer made unfortunately.


Funny how one of the looks included a “sweater over tailoring”, considering the previous articles. Was it planned? I can’t help but consider that the Rubato sweater would be too thick to actually wear under a jacket?

I don’t care much for the unusual shoe choices (or the cap) but otherwise I think look 2 and 3 are very well put together. Double knitwear like that works surprisingly well, and that coat is exquisite!

Jeff H

Thank you!


Great article Simon – would you be able to please ask Jeff which fabric he chose for the Corcos? Been looking for one just like it for the while! Love the light blue windowpane!

Jeff H

Hmmm, this was some vintage stuff that Corcos had. It’s silk and linen, my favorite mix. Sorry I don’t have more info for you


Thanks Jeff! It is fantastic.

Eric Michel

Great style, my only comment is that I am not a big fan of knitwear into the trousers, this is why I like Rubato knitwear which is short enough to provide a similar effect without having to put it in the trousers. And if I wanted to do it, I would select a lighter and more adjusted knitwear…

Jeff H

Really enjoying my rubato stuff!

Peter Hall

Nice and coherent outfits.My favourite is three which integrates smart knitwear with the carhartt pants ,less formal boots and cap. Neither top nor bottom too far apart in terms of formality and with classic proportions.

Jeff H

Thanks Peter, very kind


One of the best so far – a real awareness of both himself and the inflections of dress. Sophisticated but loose. I love that Merci watch, have come close to buying the black field watch and may yet succumb.

I also deeply sympathise with the aversion to shoelaces.

Jeff H

Thanks Maurice. Laces really are the worst


Jeff has superb taste. The Corcos jacket and Tailor Caid coat are outstanding! This article deserves to be carefully studied.

Jeff H

Thank you Scott!


The tailoring is excellent but rest of the outfits shout Pitti and #menswear to me. It’s hard to understand why anyone would wear a dark grey polo neck and scuffed brown suede loafers with that tasteful suit. I have a similar plaid jacket but wear it with an Oxford or brushed cotton shirt rather than the ubiquitous denim. The equally predictable baseball cap and sneakers just cheapen the herringbone coat which I absolutely adore. I’d wear it with a Tremelo cap from Lock’s and Boston loafers from Crockett & Jones.

If sartorial elegance are to return to our post-lockdown towns and cities, we all need to set an example by dressing up rather than down.

Jeff H

I hear you there. I picked these outfits based on how I’m really dressing at the moment and the truth is I’m not wearing ties nearly as often as I used to. It doesn’t mean I’ll never wear them again, and I still love being in a suit and tie in the right scenario, but I’m enjoying subverting the suit a little bit. It keeps things interesting for me. Ties will always be there ?. And I do often wear Boston’s with that coat, so it’s funny you mentioned that!


While I agree with the baseball cap (and to some extent, the sneakers), I think tailoring and well worn shoes is pretty common. If you look at the images from Andreas Ws article about italian industrialists, they frequently wear suede shoes with very nice tailoring – and a little patina is part of the parcel. King Charles is also well known for wearing repaired clothing and patched up shoes. In fact, I find the WORST way to wear tailoring is when everything is too neat, too new and too well polished – that’s the kind of look you see from finance bros who maxed out their credit card to wear the office uniform. The people who look comfortable in their tailoring seem to wear clothes and shoes that are well fitting, well made, well loved, well maintained and well worn. Clothes that have been with them, and grown to be part of them.

As for sartorial elegance, I don’t think you’ll set many examples wearing a suit, tie and polished oxfords (as much as I love that style myself). That look is too far away from what most people identify themselves with. I do find that when I wear casual tailoring; a PS donegal with cavalry twillt rousers, rubato knits and chukkas, or a tobacco hopsack jacket with ecru jeans and suede loafers, people do respond positively.

The trend that clothing becomes more casual has been going on for over 100 years. I don’t think it’s going to change on our account. But we can aim for more elegant casual clothes, that incorporate traditional craftsmanship.


“he’s knowledgeable, has a cosmopolitan taste level, and knows how to wear cloths with an elegant insouciance.”-Bruce Boyer.
This sums it up well, he’s a modern man of his time and generation, but not a true gentleman. The type of gentlemanly elegance you speak of Gary has all but died out. Only dandies and eccentrics would dress as you suggest (not a bad thing, but uncommon for Millennials). Still he should be praised for wearing tailoring in the first place. Better then seeing a pair of jeans with a muffin top stomach and a bum crack showing, or some toilet paper stuck to the bottom of some old scuffed trainers with yellowy brown mid soles.

Jeff H

This made me laugh

G. Bruce Boyer

Jeff is one of the guys I would point to as having a true sense of style: he’s knowledgeable, has a cosmopolitan taste level, and knows how to wear cloths with an elegant insouciance. Of course, that he’s a great guy and good-looking too is just another reason to hate him.

Jeff H

Bruce, that’s so kind! I might need to frame this. Miss you!


Paraboot michaels were my go to during the early nineties (brown leather, dusty suedes, etc.). They sold along with stone island, cp company, all inside the flatiron building on 5th and broadway! Not my cuppa tea anymore yet see they are out and about again.
Gotta agree, salva is THE trouser maker of distinction though pomella seems to be a more reasonable alternative.
Btw were any of those watches vintage?

Jeff H

Nope, both of them are pretty recent releases, I’ve just worn them a lot ?


Hello Jeff, would you be able to share the fabric codes for both the Corcos sport coat and the Tailor Caid coat? Thanks!

Jeff H

Hi there – the jacket is a vintage bunch from Kotaro’s archive, I don’t recall who wove it. It’s a linen/silk blend. Sorry I don’t know more!

Jacket is Fox and linked below!



Jeff H

This guy is such a dork!

Always a pleasure chatting with you Simon, thanks for thinking of me!


Beautiful overcoat, I don’t suppose you remember the cloth details for that piece?

Jeff H

Can’t explain it, but I like Jeff’s jumper over jacket a lot more than the one from last article, with the corduroy suit. Maybe because it’s less contrasting, or maybe because he’s not wearing a suit… But people on the street jeering? I didn’t think there were such strong feelings about the issue, despite some discussions on PS.
Apart from that, I really enjoyed all three outfits, particularly the first one, quite understated despite the bold suit. And the colour combinations in the latter two are lovely!

Jeff H

Oh they were 100% laughing at me, it was pretty funny actually. And thanks!


Well, if people are going to think you look like an asshole, I guess a rich asshole is the kind to be?

I must admit, I find it interesting that while we’re living in a society where every broguy has a strategy for crypto trading, the stock market is open to the public without middle men, and successful serial entreprenours are our national heroes, dressing in a way that is associated with wealth is so provocative. Even among people who spend thousands on tailored clothing, it seems to worry a lot of us…


It reflects the broader “casualization” of Western society that’s been happening since the end of WW1. Interesting, though, that as the middle class evaporates, we are more and more worried about indicating wealth via our clothes.


Some great outfits. Love the polo coat and over the shoulder shetland (although sure to trigger your class conscious readers). Likely generational but baseball caps are a little overdone. More interesting options. Like a PS cashmere watch cap. I do enjoy this series and admire these guys for having the courage to put themselves out there for critique. Thanks Simon.

Jeff H

Yep, that’s the one.

Rowan Morrison

Hi Simon, just a thought but it would be helpful if you would give some more details of the items featured in these articles, when you list them, for example it would be useful to know the materials or the name of the pattern used on the sports coats.and trousers, as well as the maker. This would be helpful for people who are looking for ideas on developing their own sense of style as it would help us to understand different elements that work well together. This is particularly relevant when going for the kind of relaxed elegant look that you favour (and readers like me aspire to) where one miss-step can throw off the look of an outfit.


Which Carhartt trousers are theese ?

Jeff H

These are the WIP versions. I believe they were called the Ruck. Unfortunately, they no longer make this model. It’s a real bummer because they utilized the same super hard wearing fabric but they were slightly slimmer and didn’t have metal rivets. A bit easier to wear in my opinion. Maybe one day they’ll bring them back.


Hi Jeff – sorry to trouble, may I please ask where I can find the leather strap (color/ brand?) that you’ve paired with your LMM watch? Thanks much!

Jeff H

Of course – it’s a Reid strap from Hodinkee in Dove.



Superb overcoat.
The bother of having to tie shoelaces – I think falls into the category of a ‘first world’ problem though!

Jeff H

Yes it does


There is an awful lot to like here: I really like the color combinations in outfits 2 and 3, everything is of obvious high quality, and the outfits are put together in a very personal way. In my opinion, some details of Jeff’s style push him pretty far towards the showy end of the showy vs subtle spectrum, but when you’re as young and good looking as Jeff you can get away with it.

Jeff H

Too nice, Andrew, thanks man.


Hi Simon,
These profiles just have something really special about them in that there is not one that is aping a previous one but one can see oneself in some of them and their characters. Really liked Jeff’s laid-back style and relatable persona. Even with his bulging contacts book in menswear he can still appreciate that rough-around-the-edges baseball cap and that a ladies sunglasses could work for him. I wasn’t surprised that he came up with that immortal ‘screw you’ DB line too!

Jeff H

Thank you, very kind.

Michael Patrick Porkins

About time Jeff gets some love! Always crushing it. Would have loved to see him show off some of his Dan Flashes fits, but maybe next time. All the best, Jeff!!!

Jeff H

RIP Tiny Dinky Daffy (3 people will understand this)


Jeff, really like your style and appreciate your work with HODINKEE. What strap did you pair with the Merci watch?

Jeff H

Hey Paul, thanks so much for saying that. It’s a Reid strap from HODINKEE in dove grey. It should be linked above.


Do you happen to know the material of the brown trousers? They look really nice

Jeff H

Yes, it’s Holland & Sherry Cavalry Twill from the Seasonal Classics book, another favorite of mine. It’s the 13oz Wool whipcord. I believe this was 9522205.



Thank you!

Astemir Alma

Thank you for the answer. I wanted to ask this question as well after reading the article, but thankfully, Magnus already asked the question.


Jeff, what great outfits!
Not on display are jeans – is there a specific maker/cut you like?

Jeff H

Thank you, appreciate that.

Good question. I’m on the shorter side at 5’8”, so jeans and casual pants are a bit tough for me sometimes since most companies rarely make different lengths. That’s less of a problem for raw denim and I’ve liked Oni, Pure Blue, and 3-sixteen lately.

For washed denim, I’ve actually really gotten into Acne. They make different lengths so I don’t have to hem them and their washes are great.

Also, I’m digging slightly wider fits lately and the Rubato guys nailed their denim fit. It’s fitted in the hips, slightly more generous in the thigh, and straight below the knee. I’ve found, sometimes wider fits get really sloppy in the hips and upper thigh areas and I hate that. Rubato really focused on keeping that area clean while giving room everywhere else.

Carl L

is this watch really the Merci LMM-01 “Nationale”. I can’t find any other pictures or places to buy this watch. I mean specifically with the numerals at 3-6-9-12. Was it a limited edition, sold out, maybe?
comment image
Thankful for any help. Absolutely love the look of that watch!


Jeff H