Welcome to winter

I’m so excited the weather in London has finally turned cold. Summer clothing is great, but there’s just so much more of it in winter: hats, scarves, gloves, overcoats, plus heavy-gauge knitwear and serious boots.

The key to dressing well in winter is investing in 1-3 quality items in most of these categories. A great overcoat, for example, can be one of the most rewarding investments you’ll ever make. You’ll wear it every day, and appreciate it every day. You can make do with one this year, and invest in another the year after next – perhaps a raincoat, or a top coat rather than an overcoat.

I should be receiving my pea coat from Davide at Gieves next week, and I’m very excited about it. The key, for me, is that its versatility: formal enough for a suit, but also short and casual enough to wear with jeans and knitwear. I don’t personally like rugged coats with tailoring (eg Barbour jackets), but I can see the appeal: when casual and formal wear are coming closer together, why have an especially formal overcoat?

So consider your actual needs and buy accordingly. A pea coat, for example, is also practical for commuting – you don’t have to tuck it under your legs when you sit down, and it can even be worn on a (Boris or Brompton) bike. I’ve tried and like the Harry Stedman and E Tautz versions.

Below are some more quick tips on dressing for winter – as requested by readers over the past few weeks (apologies for the delay, I must get better at writing for the seasons…). But as always, please ask any questions in the comment section and I’ll try to help.

1  Invest in an overcoat

As above. Worth stretching the budget for. Also worth having it altered in the same way as a suit, if you can. You don’t want it as slim as a suit, but a well-fitted overcoat is a beautiful thing and no one else will bother.

2  Raincoats are RTW

I know about a dozen tailors that have tried making bespoke raincoats. It’s not easy, it’s expensive, and importantly the end result doesn’t justify the effort. Buy them ready-to-wear and try to find one with a belt, to cinch some shape. Classic Burberrys are fine, but overpriced and usually not long enough. Look for a similar style elsewhere. For the rubberised alternative, try Mackintosh or the Seal-Up ones at Anderson & Sheppard (nice quilted linings – always get a lining if you can).

3  Wear a hat

Nothing is more striking while actually being quite conservative. Stylish and incredibly practical. Wear with an overcoat or raincoat, and always tilt slightly to one side.

4  More than one pair of gloves

Gloves are probably the most attractive way to add variety to a winter outfit. More interesting and unusual than a scarf. Buy one versatile colour (brown leather/suede most likely), one more interesting (peccary perhaps) and one outright pop (yellow is my favourite). When not in use, stuff into the overcoat’s outbreast pocket. 

5  Layering

Layer knitwear – a thin crewneck under a chunky shawl-collar, for example. Layer outfits –T-shirt/shirt/V-neck/scarf/jacket/overcoat. Layer anything, in fact, and have fun with the playing of colour and texture. It’s like figuring out shirt/tie/jacket/handkerchief combinations, but more fun. 

And as ever, that’s the most important thing – have fun.

Photo: Luke Carby

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John Lewis

I travel a lot and my best buy was a classic loden with a zip-in cashmere lining. It can cope with mittel european winters and the UK. I bought a long Burberry trenchcoat in 1977 which is now a tight fit (I am 6’4″ – 50″ chest) but a recent attempt to replace it failed – Burberry only produce small sizes (48″ max). Overcoats and raincoats need to be long and I do not cycle!


whats the difference between a top coat and an overcoat simon?


Four years ago you yourself gave a more detailed answer to this question; many would see a topcoat as a coat for cool rather than cold weather, i.e. a spring or autumn coat. Such coats are indeed often shorter – a covert coat is a topcoat rather than an overcoat.


Dear Simon,

Rather off-topic, but I plan to take my first Non-Asia bespoke leap next week with A&S. Fairly excited. I have a good idea of what I want (a navy SB and a pale-gray DB) but have a few directed questions:

-I would like for both suits to be a) hard-wearing through all seasons (I plan to get as much use out of them as I possibly can) and b) separable into odd jackets and trousers. What specific “navy” and “gray” cloths would you recommend? They obviously will not be worsted. I also do not mind slightly heavier cloths. In addition, I might end up having both of them made in navy (I have many gray suits). So a couple of cloth suggestions with some variation would be nice.

-From a value and longevity perspective, if I had to choose between adding a waistcoat or an extra pair of trousers, which should it be? I do wear and like waistcoats.

-I find myself preferring A&S’s DBs more than their SBs. Would you agree? For a proper SB with good finish, do you suggest other makers (the one I am considering is C&M. Yes I realize the polarity in style)?

Many thanks,


Hi Simon,

Good timing with the topic as I’ve got a question related to coats:) I’m planning to order a bespoke unconstructed light short double-breasted peacoat / sport coat. I tend to layer heavily in the autumn / winter and so would prefer something med-range cloth-wise, thinking in the range of 400-450g/m. Can you recommend something which would be suitable? Navy plain is what I’m aiming for, I’ve already ruled out flannel as it’s not strong enough.



I like peacoats but they all tend to be too short these days. I tried one from Drakes but didn’t like the way the lapels and collar worked when buttoned. I may have to consider bespoke but reasonably priced.


Simon, I’m very interested in your comment about bespoke raincoats never working. I’m about to commission a wax cotton driving coat (bit like a Barbour) for cold days in an open car. Since there are some obvious similarities with a raincoat, I was wondering if you might expand and share any known pitfalls and what to avoid?

Thank you.


Hi Simon,

Regarding peacoats, how is the quality of Gloverall? Do they manufacture them or the make them made by others?



RE: gloves stuffed in the outbreast pocket, I’ve seen a lot of pics of guys in Pitti doing this. I’ll admit it can look pretty cool (if rather affected) but I can’t figure out a way to make the gloves comfortably fit in such a small pocket. Even one glove causes a big unsightly bulge in the overcoat chest (not to mention the fact keeping just one glove there seems a bit ridiculous.)


That’s true. I bought mine in one of the Burlington Arcade’s shop few years ago because I had read Gloverall was the authentic duffle. Anyway, I am very happy with the construction, the material (80%wool and 20% polyamide) and the fit, though the buttons and lining are not that good.


What is it with the wave of unlined overcoats etc recently. I tried on a lovely looking Billy Reid Pea coat in New York on holiday. Look great on me but the huge thick seams were uncomftable and everything in suitsupply. Some really nice coats with great looking material but again, unlined and in my opinion, not as comftable.


Hi Simon,
About Burberry’s RAIN-coats: I still struggle to understand how their designers have come about with the idea of shortening them, and by doing so somehow become oblivious of the real purpose of these items. Unfortunately, Burberry’s is not alone on this trend. Why esthetic should trump function – what I guess to be the rationale behind it – is really beyond my grasp!


PS: on hats. The single item in my wardrobe that combines function, style and a touch of political – yes! – statement is my … navy blue beret basque (made by Fléchet)!

Marco Zanchi

Dear Simon

May I ask you the details for the hat pictured above? The colour is great, the proportions, too.

Kind regards, Marco


Socks – the move to a heaver winter sock is the sign of season change. I am not at it yet, so still nice cotton ones. BUT last week I was reading about vicuna socks at £450 a pair – I snorted with contempt until I had a look at them. Now I want a pair, please be the voice of reason and tell me how stupid I am. They do look amazing though ….


Hello Simon,

Where does casentino wool fall on the spectrum of winter permanent style? The coats seem to be everywhere these days, at least in the iGent community.


If you are looking for raincoats that look and feel good. I highly recommend you take a look at this link. http://norwegianrain.com/collections/all
I’ve only seen the Anderson & Sheppard coats in pictures, and obviously real life could be very different. But at least in the pictures A&S products look as dull as every other standard raincoat. The ones from norwegianrain look and feel great. The detailing is impressive. Just to mention a few things from the website : Cashmere lined front w/magnet closure, horn buttons, heat-sealed seams, recycled, hi-tech Japanese fabrics, waterproof membrane, extreme breathable, detachable hood. No I do not work for them but I am a very satisfied customer. When you have to resort to a raincoat they really are a good blend of high-tech and style. But take a quick look and decide for your self.


Dear Simon,

this is a very nice post and the timing is perfect! For me there is only one unsolved question. It is about winter boots.
I own a fine pair of welted rugged boots, which are working perfect with jeans and peacoat. But they are not suitable with a formal dress. Do you have a suggestion for a more formal boot, which can be worn with a suit or flannel trousers?


hats are ok but wear a trilby not a fedora with wide brim unless you are arty or an actor, some good hats are oput there, the bogart from melegarri is a very unusual one but akin to the trilby look. I personally wouldnt put v neck jumpers under a tweed jacket , I think it spoils the look but an original fair isle looks good. as for overcoats well its hard to beat a classical crombie with top pocket for handkerchief.


Hi Simon, I would like to add the riding Mac (available from Cordings) as a departure for occassions where a more robust wear is required. Boots are also a consideration for more inclement weather, from a sturdy chelsea to a brogue boot from, say, Trickers. On another subject I occassionally enjoyed following the advertising links but cannot see them in the new format, where are they now to be found?


Riding macs are excellent in wet weather – they combine style with practicality in a way that few other garments do, and should, I think, be worn with a flat cap. They have two disadvantages – they are not warm (though they are windproof) and are ASTRONOMICALLY expensive.


Hi Simon

I really enjoy reading your blog, thanks!

I’ve recently invested in a Drake’s cashmere crew neck, light grey, a comfortable fit. But, I’m struggling a bit with the neck line: it seems quite wide, which I was told in the shop was a more traditional feature of crew necks. Is it, and should I wear it with a shirt/polo? Grateful for your thoughts.


Hi Simon. Many thanks for all the great tips you’ve been giving us all. The one thing that I feel escapes me when it comes to winter is caring for clothes. I am faced with quite a lot of snow and it is often the case that my trousers get soaked through. As constant dry cleaning for suit trousers (and suits for that matter) is out of the question, is there anything you would recommend in order to be able to properly care for garments in the winter? Thanks for your advice.


I live in Canada where temperatures in the winter are routinely around -10 Celsius, and with wind chill it feels about -20. I been wearing my parkas such as Canada Goose and the like when the temperature dips below negative, I’m wondering if there actually wool topcoats that can keep you just as warm at that temperature?

I do have a few RTW wool coats are that decently heavy, but when the temperature dips below -5 it just not do the job.



I am trying to find a trench coat, and really like two of the longer ones from Burberry, they fit very well (may have to get sleeves adjusted)… But I can’t decide on colour.
This will be to wear when it it quite wet out, with more formal wear, I have my barbours for casual wear. I just can’t decide on colour: navy (ink), or khaki (honey). It will be for city wear, and I have a dark english complexion… Most of my suits are dark, as are my top/over coats… Should I contrast with khaki, or stay somber with navy?

I need help!



Thanks for saying Honey that’s my sentiments entirely! The British summer is so brief and often rainy and I can’t walk around in dark clothes all of the time or I might as well sit in my bedroom listening to the Smiths!


If you are going to wear a hat buy a trilby not a fedora, the fedora says “Look at Me” while the trilby is a proper mans hat . AS regards riding macs, dont get one if you havent got a nag , most are open at the front where the thighs are . They are not expensive, go brick lane


Offering my humble opinion I wouldnt buy a loden for style I would only buy one for warmth or if you are the mountains and are doing heidi’s uncle


I’m glad to say I will be in London the second week of October, and I couldn’t think of anyone better to ask regarding what type of coat bring? Some I have in mind…

Double breasted overcoat?
Flannel navy jacket?
All of the above, ha 🙂

Thanks Simon, any advice helps!


Dear Simon,

the summer is over and autumn has started and the winter will come. I want to invest in new jacket(s) and thought about some flannel with gray herringbone pattern as well as a navy corduroy suit or jacket (maybe with peak lapel).
What would be your suggestion for the autumn/winter and what seems to be most versatile?

I would appreciate your comment!



Thank you! I am excited for your post


What about a quilted jacket?


Hi Simon,
Can you do a post on Aran and Fair Isle knitwear?


Simon can I put a winter dressing scenario to you? It is a typical London winter’s day, quite cold, very wet under foot. The kids want you to take them to Hyde Park which you know is inevitably going to involve a lot of mud… what shoes/boots do you wear?!


Would love to see a “How to Dress For Spring” feature in the same spirit. I don’t see enough space given to lightweight coats which aren’t as heavy and fortified for winter as the overcoat and topcoat. Raincoats and trenches? Was just in Japan (March-April) and the usual coat for the suited man was a sort of “spring coat” which resembled a shorter trench, which would stave off rain and wind and help when the nights and mornings are cold. I had my pea coat with me and most days, that was too heavy. I think this area might be underserved here on PS.


(RE: my earlier comment about “How To Dress In Spring”)—I do mean with regard to staying warm and dry!


Hey Simon can I get your opinion on what kind of shoes to wear in harsh winter with lots of snow? Suede chukkas looks good but looks like it can be ruined by water and snow. Leather can seem to be equally damaged by the snow as well. Does that leave sneakers?


Simon – I wondered if you had any thoughts on the styling of the Billy Reid peacoats: https://www.billyreid.com/bond-peacoat-2032156?1425=13386 These were used in one of the Bond films so experienced a surge of popularity a while back. The lapels and collar in particular are not “traditional” but being someone who likes to pop a collar, I wonder if this design might actually suit.


Simon – putting truly luxury options aside for the moment, do you have any recommendations for warm socks? By “truly luxury” I’m think in the £50 and up for a pair.


Thanks – not so concerned about “smart” but more focused on warm at the moment. I will check out both options you’ve mentioned though.

Alex N.

Dear Simon,
I have been playing around with an idea for a winter suit for very cold climate (lower than -15 C) . Do you think that a shirting weight flannel could work as a good lining to a suit? Similarly to the Pommella overshirt which is quarter lined with Albini shirting flannel. I think it makes a good combo there and perhaps it may work as extra insulation. I wear my 14 oz fox flannel Pommella overshirt on summer evenings even in July in Europe as it gets chilly at the seaside and am not sure why people are so afraid of high weight of a fabric. I couldn’t wear 14oz flannel in the winter, I would freeze.
So, could shirting flannel work as a lining?
Alex N.

Daniel Zilli

Hi Simon,

What would you recommend as an alternative to a sports coat underneath an overcoat, other than just knitwear? Do you think a woolen safari jacket could work?

I am trying to think of casual layering options for a planned trip to Milan in January. For example, I was thinking roll neck, safari jacket and the PS donegal overcoat

your assistance would be greatly appreciated.


What do you think about crewneck sweaters being worn without shirt underneath?
Does it look awkward?
I really like the look of crewneck sweater by itself