Jacket and jeans: vintage cashmere from Eduardo de Simone

Wednesday, September 26th 2018
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One of the most useful things in this day and age is a jacket that can be worn equally well with jeans and with formal, tailored trousers.  

I’ve talked about this in the past, but in summary I find that for a jacket to work with jeans it needs to be:

  • Casual in style. Things like patch pockets, 3-roll-2 front, perhaps contrasting buttons
  • Casual in cut. Rounded edges, open fronts, often a tiny bit shorter
  • Casual in make. A soft construction with very natural shoulders. Often Neapolitan
  • Casual in cloth. Something with texture, primarily, like a tweed or fuzzy cashmere. Casual colours help too, like greens and browns

These are roughly in ascending order of importance. You can get away with normal flapped pockets, for example, but not with a square, structured cut.

This jacket from Eduardo de Simone in vintage W Bill cashmere ticks all those boxes.

It looks great here with jeans and a blue oxford, but could still be smart with a white shirt and charcoal trousers.

Eduardo made me both a bespoke and made-to-measure version of this jacket, as he wanted me to compare and contrast the two - I’ll do that, and comment more on the fit of this one, in a separate post.

The cloth is beautiful but, unfortunately, is a vintage piece that Eduardo had on hand from W Bill. He has enough for 2 or 3 other jackets. 

The closest thing I’ve found in current bunches is the Loro Piana herringbone cashmeres, but they tend to be lighter in weight. (This one is perhaps 13oz.)

The jacket is a tiny bit shorter than most of my formal ones, but not much, with a back length of 31 inches (neck point to bottom edge).

It has dark-brown horn buttons with some variegation. And pockets with nice curves to them.

The hip pockets, though, are actually a little straighter than most Neapolitan ones - it’s the tops with their forward, curving slope, that draw attention.

The jeans are the second pair I had made at Levi’s. (Bluer Cone Mills denim, with a slightly lower rise).

Interestingly, I find a slim jean like this works better with tailoring than a wider one that's closer to the cut of a formal trouser.

Wider jeans tend to lose their shape, and not have the clean, straight line of a slim leg. The ones from Anglo-Italian also have that approach, while the Armoury ones I have are wider.

The shoes are unlined Edward Green Dovers, in dark brown ('mink') suede and thin rubber soles.

Going back to our post a couple of weeks ago on Gaziano & Girling’s Fresco range, I do find that these unlined Dovers lose their shape a little and look more casual as a result.

But they're also fantastically comfortable, and are one of the few styles I have that can bridge smart and very casual outfits.

This is an area for shoes that I find interesting at the moment, both because I'm wearing them more and because it's a small gap in my collection. (If you look hard enough and long enough, you’ll find one...)

Shoes that fall into this category perhaps include split-toe derbys, loafers and boots, often in casual materials like suede or cordovan, and usually on slightly more casual, rounded lasts.

One way I define this category of shoe is that it has to be casual enough to work with non-tailored jackets - like the Sapayol leather jacket I reviewed recently.

The shirt was made bespoke by Luca Avitabile in our exclusive PS Oxford fabric

There about 12 lengths of that fabric left to make bespoke, and a ready-made shirt in the same style should be available next week.

Oh, and I didn’t wear a pocket handkerchief. I find it feels out of place these days with such a casual outfit.

Photography: James Holborow

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Simon – what kind of shoulders does this jacket have?


Hi Simon,

Are the shoulders pleated?


Thank you. Does the jacket feature a notch lapel or concave?


Is the lapel slightly wider than standard and have curvature to it or is it a straight standard notch?


What are the costs of these jackets (MTM and bespoke?) Thanks


I can’t see any prices in this article.
Also, where would you access the MTM product ?


If you want to sell one of the jackets (as you have two!!!) I am a very similar build!!! Email in comment submission!!!


Hi Simon
Looks spot on!
Would a darker brown work better or not be so casual?

Richard T

Great looking jacket, Simon, and it’ll be good to read your view on its fit, along with your observations on the MtM jacket too.
I agree with your view on the suitability of more structured British jackets for wearing with very casual shirts and trousers, particularly with denim, although it’s a view that has only recently crystallised in my mind. It’s a look that I’ve tried to pull off with traditional British jackets in the past, but gave up on because it never looked right somehow. It’s been very helpful to read your comments on relevant jacket styles and, having successfully tried two more softly styled, casual jackets in the summer (one RTW, the other MTM), I get it and am about to commission a bespoke autumn/winter jacket (or two!).
I’m an independently minded person, quite happy to form my own views (that philosophy degree left its legacy!), but one of the great strengths of this blog is that many of your posts (and those of fellow readers) often help to crystallise unresolved feelings that one may feel intuitively, but struggle to articulate and resolve. In this case, it’s been helpful because my entire experience of “casual jackets” has been of relatively traditional British ones and the many posts on Italian tailoring have pointed me in a direction which has prompted me to explore an unfamiliar aspect of tailoring and has introduced me to a new (for me) with very satisfactory results.
Still a fan of good structured British suits though….


Well they say style timeless.

Tweed jacket, Oxford button down, denims and suede dessert boots was my daily uniform at university.

35 years ago.


And mine today ?


Nice jacket and cloth. The LP équivalent looks like a blazer fabric.
Does a low buttoning point make a jacket more casual?


Looks very well! Congratulations!


Simon I love your taste. I only want to make a gentle observation which is this open shirt flapping about with chest hair visible is just not the way to go. You have been doing this repeatedly and you should perhaps button the button. I agree with not wearing a tie with jeans which we Yanks do and it is a ridiculous look. I do not mean to offend.


From the pics (and I know pictures aren’t very representative) it looks almost identical to the Joshua Ellis cashmere on your Richard James jacket – or is that just me?

By the way I like the jeans. As much as I love the superior make of BLA, these fit and look better – maybe a little mini lesson in that!


There’s still a clash between the tactility of the jacket – its softness, its pattern reminding one of a suit – and the rough denim & very open shirt. Also, the quality and details of the lovely jacket will always stand out from the plain and unsofisticated trousers/shirt and attract one’s eyes. It is cocktails, jazz and fine evenings against workwear, blues, daytime. Nothing against the jeans & shirt at all, though. With this combination your dark brown suede jacket will always work much better. Just my 2 cents. Still an interesting exercise, thank you 🙂


Old but interesting comment. I’m wondering about a very dark brown cashmere jacket- I’d like something to work with flannels but also jeans. Is this comment by Burt true Simon? Or can the fineness/softness of brown cashmere straddle both jeans and flannels, day and night use?


Wow, those pockets. They do curve quite a bit. I didn’t notice their full effect until the last picture. How do you feel about them, a few days in?

Have you come across the Fox limited edition “Mayfair Flannel” in person yet? It’s 50% super fine merino and 50% cashmere at 20oz. Sounds great, but on the heavy side. Curious for your thoughts on how it would perform in a setting like the above. Thank you

Dan Ippolito

I agree with Oskar; it’s an overall gorgeous jacket and I think it works pretty well with jeans, but the pockets are a bit idiosyncratic – difference for difference’s sake.

Richard Jones

Hi Simon, interesting mention about a slim jean looking better than a wider one with tailoring, I agree. Looking into this further, what outfits would you say a wider jean closer to a formal trouser cut looks better than slim (not skinny)? Personally, I find the only thing that does are my CP’s due to their length – which have a close silhouette to a formal shoe. But a formal shoe (rounded or elongated) looks odd with a wider jean. Very interested to know your thoughts.

Lovely outfit Simon.


Hello Simon, You said the Loro Piana cloth is lighter in weight, is it still appropriate for tailoring purposes? And will you be able to provide the number of the cloth. Thank you.


Given that the color is brown would the shade need to change depending on skin tone in order to avoid the ‘washed out’ look (particularly thinking of Asian/ South Asian complexions )?


The jacket hits all the right points except for the weird patch pockets. In that last pic, the backwards sloping line, seen with the front darts, suggests that the pocket rises exponentially into the armpit.

With dark denims a traditional brown leather jacket still works best.


It essentially echoes, with some variation, the classical Preppy style of sports coat, stylish casual trousers and button down with Bass Weejuns or suede loafers. Question: you now look to slim Italianate lines for ‘casual’ jackets. These shapes mesh with modern slim line fashion (the key menswear silhouette 2005-2015). The classical more structured look in UK tailoring is, in a fashion sense, older. As the fashion wheel turns to fuller, larger silhouettes (as it has in Milan – Armani, Versace, Lanvin etc. – larger, looser, more fluid lines – wider width trousers) and the slim silhouette will move out of fashion do you think your sensibilities will then alter leaving behind slim moving to accepting a larger, more fluid silhouette as a casual go to?


The fashion wheel turning to fuller silhouettes? That’s highly unlikely. The signs are all around us. Versace has been bought by Michael Kors (remember that business decisions DO affect design choices). Only this week, Hedi Slimane gave an interview to some French paper and it was like God condescending to descend from Mount Olympus, with the journalist bowing and scraping. New and Lingwood pin back the jackets on their display models to achieve 20-inch waists. Male models, even in the sartorial industry (vide the ubiquitous bloke who does Drake’s, New & Lingwood, and others) are built like stick insects. And so on.

Slim fit is here to stay.


The fashion industry is going to need something new to sell. Wider silhouette like Armani in the 80s are not at all unlikely.


“Slim fit is here to stay.”

Beg very much to differ: Y/Project, Balenciaga, Oliver Spencer,
Calvin Klein 205W39NYC, Maison Margiela, Casley Hayford, Yeezy, Raf Simmons, Gucci, Berluti, Dries Van Noten, Off-White, Alyx, Rhude, Vetements


Hi Simon,

You mentioned that cordovan is ‘casual’ here. Could you explain why this is so?

Is it because that cordovan is usually brown, or is it something to do with its texture?

I have a pair of cordovan shoes and they seem to shine in the same way as calf leather, so they have always seemed as formal as a similar pair of leather shoes in a similar colour.

Thank you.


Great look for sure. I’m thinking of having a jacket made up by Saman Amel in a similar fabric, I believe the swatches I’ve seen are from their Loro Piana books.
I was thinking of a heavier “real” tweed by Abram Moon, but I’m not sure if that will actually be too heavy and warm since most days one is still indoors. Dag had made similar observations on one of his jackets, but I do love the thought of a hearty tweed…
What’s your view here Simon, better to go with a 12-13 oz rather than 14-16 oz?

Peter K

If I understood comments elsewhere on PS this is your full time occupation now Simon. Now that you don’t work in an office do you find your style and approach to everyday dress changing?


I usually wear Jacob Cohën jeans (model 688). Unfortunately they are getting more expensive each year, prices above 350 euro are very normal. That’s why I am looking for a good alternative.

I am looking for slim fitting jeans with a narrow foot width. What do you recommend?


Mike, How about Seven for all Mankind? Ideally the European not the US ones. About €250.


Simon, a lot has been said in the past about the buttoning point you have on your jackets but there is a clear shot here about how wring you have them.

Your jeans are about your natural waist, but the button seems about three inches above that, suggesting by any normal measure that its about 1.5” too high.
Next time you commission something, ask your tailor to guide you. It will elongate the torso, and look much better on you.



I thought the lower button was generally at the level of the pants, not the buttoning point. Otherwise it would look odd.


Try Hiut slim fit. Lovely jeans and reasonably priced.


Hi Bobby, I mention wider fit from seeing , over the last 3 years or so, on the premium luxe brands Milan, Paris, London catwalk shows a definitive move to these silhouettes. Laver’s law suggests long term fashion trends repeat in 20 year cycles. Mainstream silhouettes tend to move, usually, in 8-10 year cycles, taking 3-5 years to ‘safely’ catch up with leading fashion brands (cycling through introduction, rise, peak, decline, rejection). Messing with all of these cycles is social media; bringing forth new trends overnight, extending out of date trends and ending trends not yet developed. As evidence of new silhouettes developing – extra width women’s trousers were on Italian catwalks 3 years ago, on the streets of Milan last year and in UK stores this year. In 8 years time slim cut trou. will be viewed with the same regard as the bootcut style, prevalent in 2010, is viewed now (familiar but now out of fashion). As for Kors – media reports confirm he will focus more on accessories and footwear – tailoring may take a backseat. For those interested it’s worth reading Anders Christian Madsen on who is shaping fashion in the luxe brands (Vogue 25 Jul 2018).


Hi Simon

Great article (as usual). I have been thinking of getting a jacket which I could wear with jeans too. As you pointed out it is important that the jacket present enough casual features – in that sense, I was thinking of getting an unlined or half-lined jacket with no canvas. What time of fabric would you recommend I consider? I’d like it to be a three season jacket. Are there any particular types or weight of fabrics that I should prefer given the absence of canvas? I would not want the jacket to lose its shape over time (cashmere is notorious for that).


Hi Simon – Very nice ensemble. You mention the suede Dovers tends to lose their shape after a while. Does that mean they become loose and so would you tend to size down in those types of unlined shoes? Thank you


How can they be bigger, if they are made on the same last as the lined versions? The last defines the space inside the shoe, irrespective of whether there is a lining or not. Not sure if it is clear what I mean here….


My experience with tight fitting lined and unlined rock climbing shoes is that the lining preserves the manufactured shape of the shoe.
A lined shoe will mould to the foot where there is pressure but an unlined shoe will reshape around the whole foot.

Perhaps that gives the sense of roominess and comfort in these without really growing in size.


A very stupid question perhaps:
What is the advantage of Italian tailoring in regards to the Savile Row or shall I say English tailoring.? t is a fantastic jacket make no mistake about that. But could the same tailoring be done at Savile Row? with same or similar fabrics? Or can this particular jacket only be made in Italy?


It seems like I will have to take a trip.
I also wonder if you can make a sort of priority list for when it is a clear advantage to choose bespoke tailoring? Myself I see a clear advantage in jackets, suits and shirts. Very uncertain about shoes. Knitwear is not on my bespoke list unless it is homemade. I hope I manage to explain.


Lovely look, Simon! I’d prefer jeans with a slightly higher rise, I think it works better with a jacket.

And I think that it’s a bit funny that we consider these jeans “slim”. Definitely compared to the wider fitting jeans out there, but not compared to the slim fitting jeans most brands sell. These look to be rather straight from the knee down and you seem to have some room left around the thighs. So while slim, definitely not slim fit compared to fashion brands.

The straight fitting jeans from brands like Blackhorse lane or COF are pretty much the perfect fit for with and without jackets in my opinion.


I like the curved patch pockets. They mirror the curve of the chest pocket and are gracefully cool – refined yet relaxed.

Consider some grey jeans, solid or textured. A touch smarter than standard blue denim, so they close the formality gap between jacket and jean a bit, making it possible to wear slightly smarter jackets. I wear grey jeans where dark blue jeans would be too casual and grey trousers too formal. Comfy too, in stretchy fabric.


Definitely agree re lack of pocket square.

Casual + pocket square = “look at me everyone, I’m wearing a pocket square”

Juan Huertas

Hi Simon, I´m curious as to what Dover would you recommend between the Dark Oak and the Redwood for a second pair? I have a pair in espresso suede which I love, but want something in smooth leather. I can get the Redwood at a significant mark-down, versus full price for the Dark Oak (which is the one I would really want… hence the doubts). As always your thoughts will be much appreciated!

Juan Huertas

Thank you Simon! A quick follow up: would you wear the dark oak with denim/chinos, or only tailored trousers? Enjoy Florence!


Could navy Incotex chinos replace the jeans in an outfit like this?


Very nice jacket and beautiful fabric and cut! It is maybe one of the most interesting posts, given how many guys dress up or down in that combination of jeans and blazer. Sure Simon is aware and maybe has posted on this already, but maybe the higher waisted jeans, slim or not are definitely of help with a blazer. Chadprom via bntailor used to produce a high-waisted slim model not so while ago and maybe still do and from images, I imagine Resolute 710 might also be high enough to elongate the look and hide the shirt when jacket is buttoned. I am quite ignorant on jeans, but recall images from the Italian 80’s where 501 red/orange label was very popular and the look of Milanese cut (navy or tweed) blazer with button down shirts and loafers or buckles was THE way to get dressed on a weekend. The higher the waist of the jeans the fuller or structured the jacket can be perhaps. This could be some food for thought on Simon’s great post on his F. Caraceni grey cashmere blazer, that might be harder to wear it in a sporty way. Maybe it just calls for a more classic pair of jeans and to bring out its beautiful classic cut in a sportier way. Higher waisted jeans are also practical on keeping the shirt tucked in and allow more comfort around the hip area. Tapering it (usually from inside only) could get a good slimmer look and make one enjoy the view of his beautiful shoes. Just an idea…


A question about color/fabric if I may. The brown of this jacket seems similar to your donegal Rubinacci. 1) Do you tend to gravitate more or less to one (based on the fabric) herringbone v. donegal? 2) Taking a look at this shoot with jeans and your tweed Caliendo with jeans. Same query, do you gravitate more or less to one of the jackets? (Is the muted brown easier to wear compared to the tweed?)


Hi Simon, do you usually wear a belt with jeans? In the pictures, you seemingly did not wear any belt. If you do not wear a belt with jeans, how would you tailor your jeans’ waistband (loops/side-tabs)?



Would you have worn the same shoes with this outfit if they were on the soft chiselled (606?) last?


Interesting. I’d have thought that being suede and a Norwegian split toe, would have trumped the last. Would your view change if the jeans were swapped out for incotex chinos with no crease?


Hi Simon,
I recently commented on your Oatmeal bespoke jacket by Elia, but have since found this article and have decided it is “the one” — as I’m trying to create a largely casual chic wardrobe (emphasis on denim (dark, mid-blue, white) and a couple of odd trousers with the ability to smarten any of them up with a suitable jacket as you’ve done above)
I understand this was a vintage fabric that I’m sure now 5 years later is long gone from Eduardo’s inventory, so I’ve been looking for a suitable alternative.
Two possible options are:
Loro Piana #708031 which fits the herringbone pattern most closely, but is 100% cashmere and only 300g.
Loro Piana #685009 which is seemingly a slightly smaller herringbone pattern, but is a 93/7 wool/cashmere blend and slightly heavier at 315g. Though the pattern is slightly off, this seems to most closely resemble what you have above in terms of composition and weight. https://textile.loropiana.com/digital_bunch/jackets_and_trousers/?lang=en
As for questions..
1) Can you opine on possible pro/cons of a 100% cashmere jacket vs the 93/7 blend with respect to a wardrobe geared towards what you’ve put forward in this article?
2) Do you have any other fabric manufacturers in mind to suggest where I might locate other alternatives that closely resemble this vintage W Bill? I’m not asking you to scour individual batches, as I love the hunt, but I just need a larger knowledge of fabric makers. Google has been surprisingly unfriendly in this area.


So, I had an opportunity to visit my local shop here and see the Loro fabrics we discussed above. The 100% cashmere is far too lux and won’t fit the bill. Regrettably, the 93/7 blend isn’t textured enough, I’m afraid. The pattern is wonderful and feels nice. It very little “hairiness” to it, but only upon very close inspection — far closer than anyone not wearing it would be. I’m fairly disappointed, as I had more or less put hope in that fabric after looking for hours and hours.

Not sure where to turn at this point shy of traveling abroad. I did email Eduardo days ago as a “why not” contingency, but I haven’t heard back. Seems unlikely that I will, ha.


Lovely tweed jacket. The side vents remind me I can’t recall seeing single-vent casual jackets in the wild for quite a while. Do you think they’re passe these days?
Also, snagged this jacket on a recent trip to Edinburgh and am eager to wear it when the weather turns. Any immediate thoughts about accompanying headwear? I’m not much of a flat-cap/newsboy fan and brimmed hats are foreign territory.
Thanks – new subscriber, and I’m loving digging into older posts.