not the Midwest, but not much warmer
How would I define Midwest style? COLD. That's Midwest style.
I'm not really a Midwesterner, but I did live in Wisconsin for 8 years when I worked for Lands' End. It's a place where I'd actually use the hood in my jacket, where guys wear cords like they're khakis, and where I always knew exactly where my gloves were. My memories from then are filled with things like pulling out of my garage in the morning and watching the car's digital thermometer drop from 30, 20, 10, 0, -10, -20... Or driving home late after work where the snow and the moonlight made the cornfields look like a lunar landscape. So yeah, it was cold.
But the Midwest isn't the only part of the country that faces the bitter winter... I think of Maine, or the Great Plains, towns in the Rockies or even the Pacific Northwest – they're all fighting the freeze. So your question is super applicable. Let's get to it. Rather than a definitive style per se, I think it's more about style rules:
1. Practicality first
2. Style second
I always liked this, to be honest. Putting a premium on functionality gives an extra sense of purpose when you're getting dressed in the morning. And I DO think you can still be stylish while facing old man winter. Leaning into the richness in the fabrics and construction sorta mirrors the weather in a hearty, resilient way. It's been a minute since I've lived there, but here's my 5-point formula:
1. A great piece of outerwear (or two) (or three). I'm a huge fan of topcoats, peacoats, and insulated trench coats because they are utilitarian but polished at the same time. You don't see them as often so they set you apart from the pack, and they give you more coverage since they go down to the knees. When I head up to our holiday shop in New York (December 3-12; swing through!) I will pack my navy topcoat and Cashball Travelers Trench. To me they look cool over flannel dress trousers and 5-pocket cords and everything in between. I also love the Midwest standby: a classic down parka. Ours is a little more Han Solo and a little less Michelin Man, but it is not messing around when it comes to warmth. Rather than down feathers, it's filled with Cashball, which is made from recycled cashmere fibers. It's just as warm, lighter-weight, more sustainable, and it stays together in wet conditions, so it's actually better than down. It's made in Italy, which is pretty far from the Midwest, but it's still got all the serious parka details: two-way front zipper, a big hood that you can take on and off… it's definitely a "second look" jacket.
2. Versatile boots and warm socks. A pair of weather-resistant boots are mission critical. For me, Blundstones are the one - waterproof, rugged, and comfortable as all get-out. They're tough without being too 'work boot' – I wear them to the office – and our Instagram is proof that they can go just about anywhere: country, city, Iceland. If you're going to have one boot for the cold, this is it. Now if you're gonna have twoooooo boots, I'd also throw in a pair of suede Chukkas, Playboys, Derbys, even Chelseas on drier days. This is a chance to have a boot in your arsenal that's durable but gives you a little more range in terms of styling. Depends on the look you're going for. Just make sure they've got a Dainite or crepe sole for traction. And winter is not the time to go sockless. The socks are important – we dig the ones from Chup or American Trench under boots when it's really cold, and they make great gifts, too.
3. Layer layer layer layer. When it's cold for 9ish months out of the year, you'll want some options. As you can probably imagine, even when I was in Wisconsin, I'm in a blazer every day. And I love sport coats in winter fabrics – corduroy, moleskin, tweeds, flannels. They feel right for the season but they take things up a notch. But if you're in more casual environments, sweaters are a fantastic layering piece. I'd get a variety of styles (crewnecks, turtlenecks, cardigans) and in a variety of textures (cashmere, wool, cable-knit). And don't be afraid to lean into a color - dusty pinks, heathered greens, and shades of blues can add a cheery lift on a dreary day. That can get you through a long winter.
4. An insulated vest is the cold climate Swiss Army Knife. I love a good vest. I wear mine over my blazers or under my trench or over a sweater or sport shirt. It's the perfect garment to throw on (or take off) depending on the temps. And it's great for travel... I take it to Italy just about every February when we go for work. Speaking of travel, we make a packable nylon version that's, again, filled with Cashball. There's a more refined version of that same vest in tweed (same cashmere fill) and Lavenham also makes a good one. The English know a thing or two about dressing for the cold, especially the wet cold.
5. Lean into cold-weather accessories. Hats, scarves, and gloves don't always feel like the sexiest pieces, but you need them, and looking like you're suffering for style is not a great look. So at bare minimum, stock up on ones you actually want to wear. I call cashmere "God's Polarfleece" so probably not a surprise that we make a lot in that. But it's also a chance to show a little style and preparedness. Maybe it's heavy-duty gloves in orange suede, or a Life Aquatic inspired day-glo toboggan, or a tartan scarf. You do you.
Anyway - it's been a while since I've lived in freezer-like conditions, but just remember - practicality first, style second - and you'll be alright. Thanks for the great question. Stay warm.