Anderson & Sheppard bespoke check jacket cream trousers

A couple of readers commented on the collar of my Anderson & Sheppard suit in our recent video, ‘How to look after your suit’. A&S have always cut a particularly thick collar (1.75 inches at the back for me), and John Hitchcock (who cut all of them for me, but is now sadly retired) particularly so. 

The thickness of the collar means less shirt shows above it on the neck, but it does have the advantage of keeping that collar more firmly attached. It becomes harder to stick to the neck, generally, the lower it is on the body. 

In the side-on shots above and below, you can see how thick that collar is – particularly in relation to the lapel. The point of the lapel only extends 5/8 of an inch beyond it. Combine that with the belly (roundness) that the lapel itself is cut with, and the effect is almost that of a shawl collar. 

check jacket cream trousers thick collar Anderson Sheppard

This sounds quite technical, but it is these small things that make a difference to the style of a bespoke tailor. The Anderson & Sheppard double-breasted style is one I have always found particularly flattering. I put it on and I feel bigger, stronger. Yet this is achieved without much padding or structure. 

You can see the ‘drape’ in the jacket in the picture in the top of this post. That slight excess of cloth, sweeping down into a close waist, gives me the full chest I lack. The thick collar and rounded lapel emphasise this effect – without having to resort to the big, high lapels of some double-breasteds. 

check jacket cream trousers anderson sheppard

The outfit was worn for the launch party for my book, The Finest Menswear in the World. As it was hosted by Anderson & Sheppard and Cleverley, I wanted to wear them head to toe – so this A&S check jacket, trousers, and my brown bespoke Cleverleys. 

I’ve always loved the pattern of the jacket (Loro Piana) but made the mistake of only ordering it as a jacket. By the time I thought it would be nice to wear as a suit as well, the cloth had gone. Lesson learned.

  • Grey shirt by Luca Avitabile. 
  • Brown tie (with textured stripes) by Drake’s – also displayed on the evening
  • Cream gabardine trousers from A&S. Better shown off during the day, but hey I love them and they don’t get many outings

Photography: Jamie Ferguson @jkf_man


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And did you buy any Ormonde Jayne perfume?


Surely you’re not wearing black shoes with cream trousers (top photo)?


Hi Simon,
Whenever I read this kind of reply of yours, litteraly, I feel a great relief! Indeed, somehow I feel liberated from the psychological effect of the after-6PM-black-shoes dictum!
Frankly, what would have been the point to be less chic and even less elegant by wearing black shoes on such an occasion with this DB and this pair of trousers?


Simon, I’m curious about the width of the trousers cuff; 2 inches?


Simon, this is one of the best jackets you have.

Wes wp

Simon – I see the sleeves on the jacket end in a kind of slant. I’ve noticed this on a lot of my handmade Italian suits. Is this “slant” a hallmark of good cutting, or is it an optical illusion?



Lovely jacket. It does seem to me, given that you are fortunate enough to have a long jacket, that you should Luca make you shirts with a taller collar to wear with your A&S jackets. Unfortunate to have to have separate “shirt designs” for coats by different tailors, but I guess that’s part of seeking bespoke perfection (alternatively just stick with one tailor).



That makes sense. And to be clear I meant “fortunate to have a long NECK”.

I have a fairly short neck with very square shoulders, so I couldn’t compensate with a taller shirt collar. I’ve had T&A (and Luca) make my collars taller in the back (so that they show more above the jacket), while not being so tall in the front (as that would make it appear as I do not have a neck). That has been one of the main reasons I have to stick to bespoke shirts as MTM does not offer this kind of “collar manipulation”.


David Craggs

A great Jacket – A&S are just the best and yes, it would have made a fabulous suit,

nick inkster

I am not sure I agree about the height of the collar having anything to do with keeping it up on the neck. That has more to do with collar size around the neck, and the relative fit of the shoulders and armholes. Horses for courses, but I would not be happy with this look.


I realise, Simon, that I have never thanked you for the launch party. I was in clothes geek heaven. Thank you!

Oh lord

How does one figure out the correct shirt collar height?

nick inkster

when you get the shirt height that suits you, put on your coat, then get your tailor to stick a pin horizontally across the point where coat and shirt meet. Half way up the shirt collar is what to aim for.


This is all futile, Simon. The Rake would surely disapprove of you not wearing jogging bottoms and Nike trainers. I didn’t buy it this month.


Simon, very nice jacket indeed. Brings me to a question though, slightly off topic and probably answered elsewhere already, but still … The thing is that I also have some casual jackets I like very much, but oftentimes find myself obliged, for wind & weather reasons, to put something on top of that while I am outside (the obvious solution to just wear an additional sweater underneath sometimes does work, but it’s a bit inconvenient later when I have to take off jacket and sweater first, and then put the jacket back on … not a very strong argument I figure …). An overcoat would be another option, but with more casual pants I am also a bit reluctant, even more so as I much buy into the flamyboyant-slightly-longer-double-breasted-thing … so long story short, is there a kind of “outerwear over tailored jacket” thing you could recommend? Any thoughts?

Thanks as always and best regards


Hi Simon, just picking up on ‘S’s point re. Shirts matching to jackets have you considered Robert Whittaker of Dege & Skinner (the Row’s only in-house shirt maker).


I see the sleeve is roped. I did not believe Anderson and Sheppard would ever do a roped sleeve.
Did you have to twist their arm?


I just had my first fitting for my first A&S sportcoat and it was incredible. I did ask for a roped shoulder and they were happy to oblige.


A and S never offers me that type shoulder when they made me a jacket. But my experience was not as good as expected although the jacket is pretty good


This issue of the collar is very interesting (at least to me..). When you say the collar is thick do you mean wide? I would have thought that a factor in how high a jacket collar sits is how the collar and lapels close at the front, for a DB they would typically close higher than your average SB? I may be missing something but you could reduce the width of the collar (where it meets the lapel) & it would still sit as high… It is a beautiful jacket in any case.


Tom, you could also try Mackintosh – although they’re most commonly associated with rainwear, they make a number of lovely coats that are slightly smarter than a Barbour, but will still look great with jeans or chinos.

(The added benefit of this over a Barbour is you don’t look like everybody else – New York currently feels like we’ve reached “peak Barbour”)


Simon, I’m interested in your comment re. Italian v English shirts. For those used to the English pattern (including myself) would it be possible for you to outline the differences between the two and why you consider the Italian method superior?


Hi Simon, just curious as to what collar style that is on your Luca available shirt? Thanks


Sorry to add salt to your wound. I think the pattern looks even better in suit ;P


So…..on (Italian v British) mainly hand finished v machine, wider seams (thus flatter) v narrow, more fitted cut v fuller, shaped collar band (widens around neck) v straight, finer (lighter) materials v heavier, collar band stiffer (gives better shape under jackets) v collar band of similar to collar, more fashionable v more classic, thin v heavier fusing; it’s clear about your preference…my question is why are British shirtmakers not adapting to some of these better and improved aspects of design (machine v hand finishing aside)?


That’s a lovely jacket Simon. It makes me want something similar.

I usually avoid DB because I am slight and only medium height (5’8″ and 135 lbs). I think I would be “lost” in a DB but the pictures in this post make me wonder if that is not true. Do you have any thoughts on the type of build a DB looks best on? Is there a particular style of DB that would suit a smaller man best?

I live in Canada, in a city where there are no real bespoke tailors. Do you know of a RTW maker that produces a nice DB jacket?


Would you wear black shoes with these trousers? I have seen some italians/japanese pull them off quite well although with more contrast at the top.

Dan G

Hi Simon,

I recently saw a picture of you in Florence wearing a light weight double breasted blue suit with patch pockets that I quite admired. Do you have any details on it you could share? Thanks!


Simon, kindly advise me what’s the difference between cotton twill and cotton drill trousers? Many thanks in advance


Thank you, most helpful