As people are fond of saying: winter is coming. The mercury is dropping already and it’s almost time to layer up. I’m an advocate for dressing seasonally but not many other guys are. I see most of my work colleagues wear the same shirts and chinos all year round. But autumn and winter is a time when clothes are the most interesting and you can take the opportunity to explore some different looks.
In winter, I like to layer up. Layering plays things up a bit and makes your outfit more interesting. It is also more practical as you can take layers off as the temperature changes or you go from outdoor to indoor. Now this is no new concept and some fashion trends recently have gone a bit extreme. I usually stick to 3 layers:
1) inside layer, usually a button-up shirt of some sort or t-shirt or polo/rugby shirt.
2) middle layer – I like to call this one my “indoor layer” for when I walk into air-conditioning. You can do a “shirt-jacket” type look, or a jumper (sweater), or cardigan. Thin-ish denim or workwear type clothes also work here.
3) out layer – or the “outdoors layer” – usually a coat, military jacket, heavier sportcoat like a tweed jacket, or even a heavy knit cardigan.
Winter is the time to explore some different materials. When it comes to pants, rather than the same old chinos, I like to wear flannel, corduroys, moleskins and tweeds. I also find matching more textured materials in pants to a heavier top more harmonious than say, if I wore a heavy pea coat and a pair of lightweight chinos. Plus the denser materials keep your legs warmer.
Australians are pretty boring when it comes to shirt materials. Practically every guy is wearing some sort of starchy broadcloth shirt, but there really is a huge range of fabrics out there. My interest in clothing started with the ivy/trad look so my shirt staple is an oxford-cloth button-down shirt, usually in light blue or white. I buy my shirts from Kamakura shirts, which is a japanese company doing better ivy details than most American companies. The materials are nice and substantial, and the shirts have great collar roll. I like button-down shirts if I am going tie-less because it stops the collar from going all flaccid during the day (unless you like that saturday night fever look). My second favourite material category is denim/chambray. You all know what denim looks like, and chambray is the more lightweight cousin. The heavier denims can work well with heavier coats and jackets (like tweed or corduroy). I also enjoy my flannels and I always get complements on my “dressier” flannels which are just uniform in colour but still have an interesting texture.
For knitwear, I enjoy my cardigans. You don’t see as many guys wear cardigans these days – some of them seem to think it is effeminate. In actual fact the cardigan was originally designed for a military general who didn’t want to mess up his hair every time he took his jumper off. So the cardigan is actually practical and badarse. My preference is for heavier gauge knits with a more rugged look. Lately I also really dig some of the patterned stuff like those from RRL. If you think you will be too hot in a heavy knit cardigan, you can always go for a cooler material like cotton or a cotton/linen mix instead of wool or its more insulating relatives.
If I’m wearing a tie, I also like to go for some interesting or unusual choices. In my rotation I have a wool knit with a square end (apparently they are in at the moment but mine are old as hell and starting to unravel on the lining), wool challis, tweed, and some ancient madders.
I’m pretty conservative with my colours and rely more on interesting silhouette and textures. The menswear staples are navy, greys and whites, but in winter I like to wear browns, oranges, and greens in a subdued, heather hue. Green is my favourite colour and quite under-utilized in menswear. While a lighter olive works well in summer and spring, a darker green (eg. in corduroy/moleskin, or as one element of colour in wool knit or tweed) is better suited to cooler weather. Green can also be nice in accessories like ties or scarves. An orange tie or pocket square can be a nice pop of colour in an otherwise subdued outfit. Likewise a brighter yellow mixed into, say, a wool navy/grey tie can make your outfit more interesting. I like to use some sort of neck accessory in winter – I just find it odd looking to have my pasty chicken neck sticking out of a heavy-gauge cardigan with no adornment. Plus it’s warm.
I like my footwear thick and heavy in winter to complete the outfit. Thick-soled boots are my go-to but a nice suede chukka in a darker brown can work nicely with grey flannel pants. Most dress shoes can work as well but I tend to stick to double-soled or lugged soles.
So that’s a bit about what I do. For most guys starting to dress stylishly, winter is the easiest time to experiment and try some new things, so take the opportunity!
For some inspiration, check out lookbooks from Drake’s.