The DIY Playbook Style Series – Outdoor Boots

Bridget & CaseyNovember 30, 2016 Comments

We were really lucky to have an abnormally warm fall season, but our luck has run out and the chill is definitely in the air.

casey-fall-fashion-16While there hasn’t been much snow yet, we know that it’s just around the corner. As lifelong Chicagoans, we’re both very used to it and we know how to bundle up and dress for the cold. Coats, gloves, hats, and winter boots are the norm around here and today we want to chat all about what we put on our feet during this time of the year.buffalo_check_military_jacket_fall_bridget_boots-6

Today’s Winter Staple: Outdoor Boots

We both have Hunter boots and Sperry Duck Boots and this boot combo keeps our feet warm & dry all season long. Let’s first dive into our Hunter boots…

Hunter Rain/Snow Boots

We both have black matte Hunter boots that we’ve had for YEARS and even though they’re a bit pricey, they were such a great investment. Hunter-Boots

They’re great for snow, but we also wear them for rain & even just as a casual look on the weekends. If you’re going to wear them in the snow then you’ll definitely want to get some boot socks to go with them, because your toes can get pretty chilly without them.buffalo_check_military_jacket_fall_bridget_boots-3

If there isn’t any snow, then Hunter boots sans boots socks work well too! Love this outfit on Bridget for a casual weekend look.

Now onto another favorite winter boot…

Sperry Duck Bootsboots winter

These are our second winter staples and we both wear our Sperry’s all.season.long. Seriously, can’t survive a Chicago winter without these bad boys.

They’re really warm on the inside, and waterproof on the outside, making them the ideal all-weather shoe.


Bridget has light brown ones and I have these black ones, but there are so many cute colors to choose from! We may both be adding to our arsenal this season.casey-fall-fashion-20

Favorite Outdoor Boots boots-10-pm

Hunter Boots // + 2. Knit Socks 3. Tall Socks 4. Knit Socks 5. Leg Warmers
6. Sperry Boots // + 7. Neutral Socks 8. Knit Socks


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  • shawnna griffin

    hey girls love the boots!

  • Hi ladies! I have also been a Hunter lover for years. I started out with a black pair many yeas ago. I remember feeling a bit sick about the price, but living in “Raincouver” I quickly came to the conclusion that they were well worth the $$. And then a few years later on a random trip to Costco, there was a frenzy of women around this particular table, when I got close, I realized there were Hunter boots of all colors, probably $50 cheaper than retail. And that is how the gorgeous “Hunter green” beauties joined the ranks in my closet. Last year I started noticing the Sperry boots, on your blog and elsewhere. I bought them and LOVE them so much. We don’t get a lot of snow here, but I live near our local mountains and they are perfect for hiking the trails with my fur baby. And they are darn cute. I tell people when I wear them I feel like I am walking on marshmallows! Great post!

    • Kerri we are shoe twins! So happy you love your Hunter boots & Sperrys. They really do feel like marshmallows…you’re so right!

      And Hunter Boots at Costco?! That’s awesome!

  • Trang

    Sperry duck boots are my favorite. I wear mine almost everyday now!

  • Kara D

    As a fellow snow-resident, I do have to ask – do you wear your Sperrys when the snow accumulation is high, or is that when you’ll revert to wearing the Hunters? And then do you wear them (either Hunters or Sperrys) all day long at work, or bring in another pair to wear inside?

    • These are great questions Kara! The snow certainly makes things hard.

      When I commute, I often wear my hunters or sperry’s and then I’ll change into other shoes when I get to work. My legs can get kinda hot wearing either of them all day long inside. If I’m outside like “playing” in snow (ha…not sure when that happens), I’ll usually wear my hunters with the high socks, so my legs don’t get wet!

      Hope that makes sense! Ugh…winter!