Essential Winter Outerwear

I've always been kind of averse to outerwear. The good stuff is so expensive, and the cheap stuff is so ugly. Therefore, I've made it through three Chicago winters (and many more Pennsylvania ones) with no real winter coat, no boots, living in layers and thick socks. However, I got an early feeling this year that this winter was going to be particularly rough (and man, I couldn't have been more right). More significantly, I took on a project this year to write a course on dressing seasonally for Cladright (more on that below), and it really inspired me to finally step up my outerwear game.

Honestly, I was still going to save this post for next year, thinking it was too late for you readers to get much use out of cold-weather tips, but hell, this winter is never going to end, so here are my biggest and best new gear investments:

Coats: 

Mid-Length Duffle | Gloverall

Between two coats I have been able to combat pretty much anything this Chicago winter has thrown at me. On one hand, I have this incredible Gloverall wool duffle coat that keeps me toasty, even when the temps are friggin -11 (before windchill). Honestly, this purchase alone gave me a newfound respect for winter outerwear, as I think it's the first time I've really been warm through the whole winter. 

Ranier Parka | Frank & Oak

On the other hand, I recently picked up a lighter waxed cotton parka from Frank and Oak that I reserve for rain, snow, and everything wet in between. As much as I love the Gloverall coat, if I wear it during heavy precipitation it gets a bit...soggy. Since it's usually a bit warmer when it snows, I've taken to throwing on this parka over a few layers to stay warm and dry.

Boots: 

Second to my Gloverall coat, my footwear purchases this winter have had the immense effect of waking me up to the idea that my toes don't have to be freezing from October through March. Again, I made two purchases:

Norbeck Boot | Ralph Lauren via Macy's

First, I caught a pair of tan suede boots on a great sale from Ralph Lauren. It looks like these are sold out at Ralph Lauren, but Macy's sells it as well and has a few sizes left. Ideally, I'll get some dressier (leather soles) and more weatherproof (non-suede uppers), but these have been amazingly handy. With the help of some Allen Edmonds suede spray, they've gone through slush and snow and barely shown the wear. At the same time, the lugged sole is thick enough to keep my feet off the freezing ground (and much warmer), but is still trim enough to wear with a heavier winter suit. 

8" Bean Boots | L.L. Bean

However, last month we caught some heavy snow followed by a really warm day and lots of rain and Chicago turned into a giant, ice-filled lake (as did my living room, but that's another story). As rugged as those suede boots have turned out to be, I decided it was time to get something truly weatherproof. From there, the decision was easy as I've had my eye on a pair of Bean Boots by L.L. Bean. While they sell out in-store and online pretty early in the season, I was able to find a brand new pair on eBay. You can also pre-order them now for next season. The things are just straight up awesome...I feel indestructible, stomping through snowdrifts and puddles without a care in the world.

As I mentioned above, I wrote a course on dressing for the Fall and Winter for Cladright, which is a member-based style education program run by Barron Cuadro of Effortless Gent. Cladright is an awesome resource all around, with more lessons as well as discussion forums, interviews, and a variety of member perks. Enrollment only opens periodically, but keep your eyes on the site, because I believe Barron is planning on accepting a new round of members pretty soon (OR, sign up for the e-mail list and get alerted).