Dressing yourself in the winter can be tough. If you live someplace where it gets really cold, it’s easy to grab your parka and go. I want to talk about how you can put a bit of effort into your outfit during the winter and stand out from the rest of the guys while still maintaining your warmth and comfort.

Growing up in the Midwest (Cincinnati, whattup?!), I learned from a very early age that if you wanted to simultaneously look and feel good during the late fall and winter months, you had to learn how to layer and accessorize. I can remember too many times thinking that it was going to be warmer than it actually was and dressing too lightly, thus freezing my ass off all night and therefore having a bad time. Also, on the flip side, throwing on a heavy coat because of how cold it was outside only to sweat through my shirt, not being able to (or not wanting to because of being so sweaty) take off my coat once I arrived to my destination. I started to learn that certain fabrics and pieces were key to my comfort and style. I want to tell you about those pieces today!

First, a wool jacket/blazer/coat. Wool has taken serious turns towards comfort after years and years of itching and irritating. A nicely designed wool blazer or jacket, like this one from J. Crew is a great piece to have for the winter because it keeps heat in better than a typical blazer or jacket because of the fabric. It’s also not going to be so big and heavy that you can’t wear an overcoat with it as well for those super cold nights. Throw on a sweater for an additional layer of warmth and style differentiation, if you so choose.

Next, flannel! It’s not just a lumberjack’s material anymore. More brands are putting out awesome styles and cuts of flannel shirts so you don’t have to look like you’re competing in a Paul Bunyan look-a-like competition. I actually got this shirt at K-Mart, believe it or not. It’s so soft and it’s also going to provide an extra bit of warmth on it’s own due to the fabric. Don’t be afraid to layer a heavier sweater over a flannel shirt, too. They also even work with a knit tie, office gents!

Moving on…stylish boots that you can beat up! I’m a huge fan of these boots from Aldo. They weren’t crazy expensive ($150), but they’re made very well and I’ve worn them in every type of condition. It’s nice to have a pair of shoes that can get dirty without my freaking out. Also, that will last through a snow or rain storm but still look nice once you get inside. No matter what your budget, lots of brands are making stylish duck boots, combat boots and rain boots alike. Get out there and see what you’re into.

Lastly, accessories! For years I can remember guys hating on my scarves, gloves and hats, saying that they’re too feminine or just simply not something they’re interested in wearing. I think that’s silly. If you are this type of guy or simply someone who doesn’t know how to accessorize, start slow. Go to Urban Outfitters or Target and find a plain scarf or hat. Something in black, grey or navy so it’s easy to be worn with all sorts of looks. When it’s cold enough, put it on and do your best to forget it’s even there. Enjoy the warmth and comfort and know that you look good. [Tip: do not wear a sports beanie or something with a logo on it to go out at night. It looks sloppy and downright silly with your nicely fitted jeans, plaid button up and boots.]

Overall, think about it this way…if something seems strange to you stylistically, think about how you can tweak it to make it work. Don’t be afraid to take chances. If combining a wool jacket, flannel shirt and scarf aren’t typically your go-to moves, do it once and see how it goes. If it bombs, it’s only one night. No one will remember it a month from now. Yet if it works, you’ll make a big impression and it will start to allow you the freedom to try new things more often, which is how you develop style!

Please don’t hesitate to ask questions! Thanks for reading!

Stay smiling, my friends!


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About the author

I'm Parker York Smith, a curious dude still very much figuring everything out. I hail from the Midwest but have been dwelling in Los Angeles for the last few years being a pretty stereotypical west coast transplant. I'm a fashion geek, I love to walk (a LOT) and I do my best to find the bright side. I'm extremely excited about this blog and hope that (with some hard work and luck) it turns into what I believe it can. If you have any questions, comments or concerns, please get in touch with me via my social networks (which can be found in the sidebar) or email me at

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