Double breasted flannel suit anderson sheppard

Everyone gets dressed in the morning. Most put no thought into it; a few put too much into it. 

My approach, formed through nothing more than hazard and habit, is to do one of two things: 

  • Pick out one piece that I really want to wear (usually something new, often something unusual) or
  • Pick out an outfit I already know I like, and fiddle around the margins

With the outfit shown here in Milan, for example, I wanted to wear my royal-blue flannel DB suit from Anderson & Sheppard. Because it’s still one of the most beautiful things I own, and it’s not really office attire. 

Only dark-brown shoes really go with it: black or tan create too much contrast, when it needs the opposite. So I picked by Edward Green Top Drawer monk-straps.

Equally, a white shirt can work, but blue is much better for reducing that contrast, so a plain spread-collar shirt from Luca Avitabile.
   royal blue flannel and orange tie

Now the tricky bits – the tie and the handkerchief.

Soft, autumnal colours achieve something similar to the softening of the brown shoes and blue shirt, so I considered browns, oranges and greens, before selecting this seven-fold untipped tie from EG Cappelli in a burnt orange. 

Helpfully the tie has a blue geometric device in the print, which makes it a little easier to sit with the blue of the suit. 

For the pocket square, again I considered several muted colours – including muted variations on white linen – before selecting a Drake’s silk/wool handkerchief in green and navy. 

Given the cold, wet day in Milan, a scarf was also a very useful thing to have in my briefcase, and grey is a very versatile option. Other colours as mentioned above, such as browns, would also have worked, though might have risked a clash of too much colour.

Double breasted flannel suit

The alternative dressing approach is to pick out an outfit I already know and like, and then give it a touch of originality.

It’s hard to keep all these outfits in my head. Most of them are scattered over the past nine years of this website, but I do have a folder with them all in to scan through when I’m drawing a blank.

So for example, I like the monotone simplicity of this outfit I wore to photograph my new Ferdinando Caraceni jacket and Simone Abbarchi shirt. I know not everyone agreed, but for me it looks smart, subtle, young and contemporary, which is not an easy combination to achieve.

In order to retain the same approach, but avoid wearing exactly the same thing, I have worn it recently with a navy Friday Polo and my Solito navy-cashmere jacket. And I have worn a paler grey shirt and chalky navy tie. 

Or as another example, I really like my tan-corduroy suit from Anderson & Sheppard, but nearly always wear it with a blue shirt and grey cashmere tie. (As with all hyperlinks here, you can see a photo of it at that link.) 

So to change things up, I have paired it with a brown-and-navy grenadine striped tie on occasion, or a deep green woollen tie. 

Little things, but they make a difference. And if they’re good enough, they get added to the file for future reference. 

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Great post! I assume it varies massively, but what is your normal progression in terms of elements in an outfit? E.g. Suit, shirt, tie, shoes, socks, pocket squares. Interesting for someone who wants to avoid repetition of outfits.

Adam Jones

A folder of outfits…..there is your next book ready to go. The permanent style lookbook!


Love these posts! As with Adam a look book of outfits (i.e. a curated re-visitation of the archive) would be a great, and helpful, book. FYI the website Looktastic, under How to Wear/brown jackets, has the Pitti shot of you. A couple of related questions. I have a similar cord suit (SB) but find it difficult to make it come to life due to the shade and older cut, how might this be achieved? Also, re. wardrobe management, you’ve mentioned you store out non-season wear. Facing a similar problem can I ask how you store; storage bags, garment rail etc.?

Oh lord

Dear Simon,

I work in a law firm, where most of the people wear suits without tie. I only wear suits with a tie, so I also wear grey pants and sports coats. The sports coats I have are dark green tweed, dark blue cashmere, dark brown hopsack and double breasted unstructured blue light weight wool. What would you recommend to buy next that I could wear 3-4 seasons? It has to be fairly formal… If you have more than one tip, I appreciate that too!! Keep up the good work.

Oh lord

Great, will do. I am in a bit of a hurry though, so may you disclose what type of fabric, weight and pattern?


Love the suit. I have a couple of bespoke suits from GB. Both are single breasted. I’m thinking of a navy db for my next one but am concerned it might be too formal. Would you recommend getting another single breasted for versatility?


Hi Simon,
I think most PS readers if not all share your taste. I find this one very chic. Strangely enough, in my case before going to bed, I already have my outfit in my head, so to speak. And usually in the morning I help instead my girlfriend choose hers.


Hi Simon,

Michael at C&M is making me a navy and a cream suit for summer in lovely LP seersucker.

Keen to hear your combination ideas on: 1) navy jacket (DB) with the cream trousers, 2) cream suit as a whole, 3) just the cream jacket, with your trouser ideas. Any other permutations please suggest.
Greatly appreciated.


Also very much looking forward to the publication of the Permanent Style Lookbook…!


What a great suit – the Royal Blue A&S DB – but why do you say it’s not office attire? If I couldn’t wear this for work, I’d change my job!
On the scarf front – is that a Begg & Co silver grey?


And the scarf?


when you get dressed do you put your left sock on first, or your right?


Hi Simon, it’s the unwashed Kishorn, right? Did yours also fluff initially, fairly visible on a darker background like that blue flannel? Does it get less with time? I much love the fabric and just wonder what to expect from here.. thanks.

Christopher Martin

To organize my clothing I use the Stylebook app for men on my iPhone. I took photos of every piece of clothing, and organized them into outfits inside the app. I can then assign them to a day in the calendar. It’s especially helpful when planning what to pack for a trip.


GM Simon, I live in the US, Washington DC, I’ve always worn bespoke or MTM suits; given the fact that I live in the US, how can I go about having an Anderson & Shepperd suit made?


The royal-blue DB is a beautiful suit. Could you please provide the full details as I am thinking of getting a similar one ordered.


Hi Simon.
Although I think white shirts can look great with light coloured suits I am beginning to develop a phobia of wearing them with dark coloured suits. I see that you tend to wear more blue shirts than any other colour. Do you find blue to be the most harmonious of shirt colours?
Many thanks


With regards to the Begg & Co scarf, do you recall which specific scarf it is? Based on the other comment I thought perhaps one of their silver grey but the fringe does not match that of the photograph.


would there be anything currently available that comes close to material, weight & colour? Something like this perhaps?


Do you think this jacket would work as a separate, perhaps with mid or pale grey trousers?

I’ve wanted to commission a royal blue flannel DB ever since I saw one dressed beautifully in the window of Hackett a couple of years ago, but have never quite been able to justify it on grounds of versatility. Not quite business attire, not quite smart-casual. Kind of suitable formality for a summer wedding, without actually being suitable for summer (being flannel). Wearing part of the suit as a jacket might help me justify it a little more to myself….


Hi Simon,

What’s your go to outfit when you’re suddenly caught in a rush when there is no time to consider what to wear?

I struggle picturing you grab a pair of jeans and a T-shirt.


I think I recall that you mentioned this is one garment where you actually both enjoy and dread wearing because you fear every time you do so, you’re chipping away at its lifespan. Could you disclose some info on the fabric?


Hi Simon,
Thanks for the response. I can’t find the exact article, but I think it was where you were taking questions from your readers; some of the questions asked were: “what garment gives you the most pleasure wearing?”, “what’ your most versatile piece in your wardrobe?”, “what do you regret making in bespoke?” etc.


Hi Simon,

Yes, my apologies, I think my faulty memory directed you to the wrong article. Unfortunately I can’t seem to recall the source, but I’m fairly confident you were referring to this exact garment being lovely to wear but simultaneously a bit fragile. Anyways, I thought this cloth really manifested the drape cut to a tee, so I was wondering if you still remember which bunch it originated from.