Midwestyle’s Favorite Outerwear

If you’re anything like us, whether your city got snow yesterday or you’re excited to finally wear your winter coat, you’re itching to dig out the heaviest jacket you own. But before we close the book on autumn entirely, we realized that we’ve got a few old fall favorites that have been treating us well this year. Which made us curious: What’s one of your favorite pieces of outerwear that you look forward to wearing each year?

Here are some of ours.

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Seth: I ain’t got no shame, so I’ll admit it: When Jeff was still living in Chicago, and because I didn’t start off as the most adventurous wearer of clothes, I often jacked his style—even right down to seeing something new that he’d purchased and thinking “Ooh, I guess I could pull that off,” and having him pick up another one for me. That’s exactly what happened with this field jacket, which cost a mere 30 bones on sale. And just like Jeff, it has never led me astray. It’s what I always reach for when the wind picks up in the second half of the year. It’s got pockets galore. And the reinforced shooting shoulder reminds me of being back on the farm in Missouri with my trusted 20-gauge over-and-under. Field jacket by Levi’s.

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David: I picked up this “Skiff” jacket earlier this season because I’m a sucker for wool. But having worked through a few less satisfying coat purchases, I knew exactly what I was looking for this time around. After having spent the end of summer trying to justify much more expensive options, this snap-front, fitted-but-not-too-fitted lil’ getup came into my life. It wasn’t cheap, but I’ve made enough mistakes in my life (clothing related and not) to feel good about fall-ing (get it?!) for a new go-to. With this, this, and this already in my closet, lord knows another navy blue jacket better be pretty close to perfect. I never loved my double-breasted peacoat, and anything with a collar that won’t stand up and cover my neck is going to be disappointing. So far the Skiff jacket has been very satisfying. The cut is slim enough that layering requires some creativity, but it’s totally worth it. Skiff jacket by Wallace & Barnes x J.Crew.

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Garrett: Call me a purist; call me a traditionalist; call me boring. When it comes to my favorite piece of outerwear, my go-to is my Spiewak Dugan peacoat. This thing is as throwback British navy as you can get. I picked this baby up three years ago for $6 at Urban Outfitters. Yes, $6. Sale + sale + discount = magic. The reason this is my favorite piece is because of it’s versatility. I’ve rocked this with wingtips and a suit as well as my destroyed denim and some NB’s. It’s tight like a tiger but hugs my curves in all the right ways. It keeps me warm on cold nights and when those Chicago winds pick up, the collar goes up as well. It’s a staple in my winter lineup, and I don’t see that changing anytime soon. Wool peacoat by Spiewak.

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Jeff: The ideal shape and texture for a leather motorcycle jacket for me is a little shorter than usual and a little rigid. I found this bad boy in either Kansas City or Chicago—I honestly don’t remember but I know that I paid under $20 for it because…it’s already had some mileage on it with the paint brush. A paint brush you say? Take a closer look and you’ll see dancing skeletons and flames on it. Yeah, I bought it to paint over it but never ended up doing it. Whatever, man. They grew on me. Vintage leather jacket, maker unknown.

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Joe: I snagged this fella on sale last year, and it has easily become my most prized possession. The wool-cashmere blend is incredibly soft and warm, perfect for wintertime weather. Typically, a topcoat is worn over a suit as a dressier option for outerwear. However, given my obsession with it, I wear it very casually too (collar popped, of course). This year I want the same coat in navy and gray. Too much, you might ask? Maybe. But I’m doing it anyway. “Ludlow” topcoat by J.Crew.

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Chris: I recall when I was a young lad, and the big box lords of clothing deemed me “husky.” My parents fought hard to get me in a pair of jeans, however I vowed to wear nothing but sweatpants the rest of my life because of their forgiving fit. Then came that one day (of many) my mom took me shopping at our local Salvation Army. I will never forget my favorite purchase: a Levis denim jacket. I littered that thing with my favorite patches and buttons: TMNT, White Sox, Bears, Korn.

I’ve been on the prowl for a trimmer denim jacket ever since. During one of my late-night drunk Etsy searches, I came across the perfect item: “Vintage Levi’s denim jacket, size 34.” One week later, I received it in the mail, and it has proven to be the most versatile piece in my wardrobe. I know it’s true “vintage” because I did my homework. It doesn’t have lower hand pockets; it has single row stitching; and I have the Big E red tab with two pockets and vertical pleats on the front. I wear this layered under sport jackets and layer it over sweaters, vests, and ties. Denim jacket by Levi’s.

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Jonathan: I picked up this “slick” coat back in June, via the annual Steven Alan sample sale. Don’t remember what I paid for it, but all I can remember was, “Hey, SALE!” (Hands over credit card.) Although I couldn’t wear it as soon as I got it—which is always a bit deflating—I haven’t taken it off since the weather turned. Technically a rain slicker with a detachable hood, I’ve found it roomy enough to throw a sweatshirt + denim jacket underneath with ease (and for this I’m a fan…’cause options.) Slicker by Steven Alan.

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Cameron: Being the layer-er that I am, I’m not one for “coats” per se, which is why this Isaora down pullover has been so clutch for me when the temperature drops. I know, I know – I look like the Michelin Man, or an astronaut, or a guy who took a bunch of old bike tires and sewed them into a sweatshirt. I get it, the thing’s weird. It’s also deceivingly warm and stands well on its own, though often times I throw something on over it – be it a denim jacket, an oversized cardigan, or a zip-up fleece. While that final layering piece helps, it’s the pullover that’s doing the heavy lifting in terms of keeping me warm. I grabbed this guy on sale last winter from Isaora’s website and haven’t looked back. Down pullover by Isaora.

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