Fall and winter are my favorite seasons for clothes. Few things feel better against the skin than wool flannel trousers and brushed cotton shirts; few things make you feel braced for the world like a tweed sport coat. Casualwear this time of year also tends to be more interesting – parkas, leather jackets, and chore coats, sometimes layered in unexpected ways. There are simply more ways to look good this time of year than in the spring and summer months.
One of the great things about style this time of year is how affordable everything can be if you’re a smart shopper. You can take the workwear route by pairing raw denim jeans with cotton sweatshirts, military liners, and army-surplus jackets – each of which can be had for under $75. For something slightly dressier, vintage pea coats and duffle coats can be bought at local thrifts for no more than $150.
Alternatively, you can invest in just a few pieces – a couple of good coats, a nice sweater, and some great shoes – and use those to carry you through the season. Whereas shirts and pants have to be cycled through daily in the summer, you can use one or two coats in the winter without anyone raising an eyebrow. If you get classic pieces, you can build a wardrobe slowly – a coat purchased one year, a pair of good shoes the next – which allows you to spread the cost.
Some suggestions on how to dress your best for winter, whether you like classic tailoring or something more casual:
1. Buy Good Outerwear: It’s worth stretching your wallet a little to get the best outerwear you can afford. If you splurge a little more, you can often get away with spending little on everything else.
For this time of year, I really like long topcoats. Single breasted, heavy wool, with a length that ends around your knees. Long coats are a bit trendy at the moment, showing up more on runways than they did just three years ago, but they’re also a genuine classic. You can layer one over a suit or sport coat, or dress it down with a chunky sweater and some jeans. The contrast between classic tailoring and casualwear in this case often makes for a good effect.
2. Accessorize with a Scarf: Scarves add a bit of dash to an outfit. They lend color, help frame your face, and add a bit of visual interest down the front of your chest. Aim for something that’s at least 64″ long, so you have enough material to tie the scarf in different ways, and find a color that complements your wardrobe (I like mid-gray, navy, and burgundy). Merino wool and cashmere will be your softest and warmest options; lambswool can be itchy unless it’s blended with angora; and acrylics should just be avoided.
3. Get Textured Knitwear: Smooth merino knits can be great for layering underneath sport coats, but textured knitwear is often more striking and visually interesting. You can get them as lofty lambswool Shetlands, cabled Arans, flecked Donegals, or brightly colored Fair Isles (the last is more patterned than textured, but you get the idea). Don’t be afraid of going beyond the classics with your knits – I find those are often the ones I reach for most.
4. Find Bad Weather Boots: It’s hard to look well dressed without good shoes, but also hard to find shoes this time of year that can stand up to the weather. Wellingtons, LL Bean boots, and even heavier work boots can be great for casual options. For something dressier, try pebble-grained chukkas or wingtips with a storm welt. They’ll require a bit more upkeep – polishing, brushing, and the occasional wipe down with a diluted white vinegar to treat salt stains – but they’ll also look terrific with tailored clothing.
5. Flip Up the Collar: This is probably the easiest way to make any winter outfit look better. Not all coats are designed in a way that allows the collar to be worn up – a lot depends on the coat’s material and how the collar has been cut. That said, try popping the back and see how the front splays. A flipped collar can be a great way to keep out the wind, frame your face, and generally make an outfit look more stylish.
