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Winter is here! We’re back to that time of year when the snow blows and the wind nips, and all you want to do is curl up in a blanket with a mug of cocoa. But that’s only fun for a day or so, and then it’s time to break out the layers. I used to dread Chicago winters, but after investing in some key pieces, I’m having much more fun!

I’ve spent several years working in a bicycle store in Chicago. While I’m not the person out riding when its below freezing, my friends are the ladies and gents you’ll see on bikes in a snowstorm. Their advice and recommendations have been invaluable to keeping warm and cozy regardless of how I’m traveling. If you’re looking for advice on how to survive winter bike riding, check out Let’s Go Ride A Bike’s incredibly thorough Guide to Winter Bike Riding.

For a more whimsical take on winter dressing, I just read Gala Darling How to Feel Fabulous When It’s Frigid Outside and it made me smile. One suggestions was to wear a bit of glitter to cure the doldrums. When it’s dark at 4pm or gloomy all day, a bit of style goes a long way towards staying sunny!

Here’s a guide to my current winter favorites:

1. Ibex Coppi Cap

I get so many compliments about how cute this hat looks! Plus the merino wool is so soft. I keep it in my purse at all times for emergency warmth.

2. Icebreaker Women’s Mayfair Jacket

This thick merino wool jacket was a big investment, but I’m constantly impress with its quality. Merino is amazing at regulating body temperatures. This means you’re warm in the cold, but not overheated when you step into a crowded store.

3. Thermos Vacuum Insulated Travel Mug

A hot drink is important for staying cozy. The carabiner clips it to the outside of my purse for easy access.

4. Po Campo Pilsen Bungee Handbag

I love cheerful colors in the winter, and the Chartreuse Poppy print would brighten a gray day! One of my tricks in winter is going to a hot yoga class. Be prepared to be warmed from head to toe. The Pilsen’s bungee straps secure a yoga mat so your hands are free for that hot drink.

5. Icebreaker Women’s Bodyfit 200 Leggings

How can these tights be so thin, yet so cozy? I can even fit them under my skinny jeans.

6. Icebreaker Women’s City Lite Crew Sock

My newest merino socks, these are thin enough to fit into my regular shoes but have extra padding on the soles. The padding makes them nice and comfy, but I’ve also noticed it blocks out the cold more. I hate feeling a chill creep up through my toes!

7. Smartwool Women’s PHD Outdoor Medium Crew Sock

The thickest, squishiest socks I own. Also merino, they have lasted for years!

8.  Gore Bike Wear Fusion SO LADY Jacket

Finally, my secret weapon. I’m not the biggest fan of very sporty looking jackets, so I originally got this with only bike rides in mind. Three winters later, I put this jacket on almost everyday! The Fusion has Gore’s Windstopper fabric, and it lives up to its name. I love a cute jacket, but most can’t stand up to Chicago’s wind. Layer the Fusion underneath, and I feel stylish, warm, and happy!

I love all these products, but I’m always on the lookout for something new! What do you wear to stay warm and cheerful on a cold day?

12 responses to “Keeping Cozy Through a Chicago Winter”

  1. Susan says:

    I second the GORE Fusion jacket! GORE knows jackets like nobody else and the Fusion is my go-to jacket for riding to work in Chicago winters, cross-country skiing, and regular old hanging out. I love the handy forward-facing pockets. If only they made it in a tweed! Another secret weapon for winter riding is a Buff to cover your face. Not only does it help with warming the air you breathe but it protects your skin from all that wind and cold (which you’ll be thankful for when you hit about 45!) Buffs come in about a million different fabric prints so you can cheer yourself up with those patterns, too. I love your Ibex and Icebreaker suggestions, especially the Mayfair jacket. Gotta start saving for that one!

    • Robin says:

      Glad to hear there’s another Fusion fan! That’s been the favorite with the ladies at my bike shop, both employees and customers. But I would be in heaven with a tweed version! I hadn’t heard of Buffs before, but I really like the idea and the patterns. I was using a cotton scarf to cover my face, but that gets too damp from condensation. Time for an upgrade.

      I’ve been eying the Mayfair for a few years, and I’m so happy I finally bought it. I get so many compliments, and it was one of those that sparked this post. Thanks for adding your suggestions!

  2. Nice post! Really classy. I’ve always wondered about biking clothes for winter . . .

    • Robin says:

      Thanks! Staying classy makes braving the cold much more fun. I’d read through the posts on Let’s Go Ride a Bike for a ton of winter bike riding tips!

    • Robin says:

      You should also read Elizabeth’s post on BikeCommuters.com. She’s linked to it in the the comments here. It’s a very thorough head-to-toe for winter layering, and I’ve personally seen her biking through tough weather!

  3. E A says:

    Great tips… I second the need for a ‘buff”. I own one by Hedz and wear it nearly everyday – either layered or on its own.

    Also – the wool hiking socks you recommend are definitely cute – mine are just standard but warm!

    (I posted about my tricks a while back – http://www.bikecommuters.com/2011/10/24/layering-as-easy-as-1-2-or-3/)

    • Robin says:

      I just read your post, and I also over think everything! The trickiest part is when the weather changes suddenly and you have to rethink your normal outfit.

      I need to get a Buff in a sports fabric. I’ve been trying another brand’s fleece version, but this one also gets damp!

  4. […] December, we wrote a blog post about¬†Keeping Cozy Through a Chicago Winter. We’re always looking for new gear, and these are our latest picks for adding a bit of style […]

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