Cozy Casual Winter Outfit with Payless

Cozy Casual Winter Outfit with Side Zip Ankle Boots from Payless
Well, this is it! Day 25 of 25 Days of Winter Fashion! We made it! I wasn’t sure if I was going to be able to pull this one off, to be honest with you. The weather hasn’t been the most cooperative, and daylight hours are at a premium this time of year. I need to find a good indoor photo spot because word on the street is winter 2017 is supposed to be a doozie.

I’m excited to partner with Payless for the last post in this series, and I have a $100 Payless gift card to give away, so stay tuned for that at the end of this post.

It was bitterly cold outside the day we took these pictures, so I bundled up!

Cozy Winter Outfit with Side Zip Ankle Boots from Payless

Cozy Casual Winter Outfit with Side Zip Ankle Boots from Payless

Cozy Winter Outfit with Side Zip Ankle Boots from Payless

Cozy Casual Winter Outfit with Side Zip Ankle Boots from Payless

These side zip ankle boots remind me of the Petty booties from Sam Edelman, but they’re a fraction of the price. They look really good for the price point, and they’re comfortable too. I know a lot of you need a lower heel, so these are perfect. These are getting sold out quickly online, but they’re still available in some stores. A similar style is this double zip shootie.

I get asked a lot about what to do for socks with ankle boots in the wintertime. I try to match my socks as closely as I can to the boots and pants I’m wearing. In this case, the boots and jeans are black, so I wore black socks. I like a thin crew sock, like these fleck crew socks at Payless.

Cozy Winter Outfit with Side Zip Ankle Boots from Payless

I found this cozy cardigan at Target, and it’s currently on sale for $17.99. It runs verrrry large; I’m wearing an XS.

I wore a long-sleeve tee underneath and topped it all off with a wool plaid blanket scarf. I love how thick and big this scarf is. You can use it to wrap up in or wear it around your neck the way I did for this post. It’s bulky, but warm.

This is the perfect outfit for a winter outdoor activity where you want to look stylish, but you need to be warm and wearing comfortable footwear.

Cozy Winter Outfit with Side Zip Ankle Boots from Payless

Cozy Winter Outfit with Side Zip Ankle Boots from Payless

side zip ankle boots c/o Payless (similar style) // sunnies c/o Ray-Ban // grey cardigan // long-sleeve tee // similar black jeans // plaid blanket scarf // faux pearl earrings // moto hobo

Be sure to visit Cyndi and see the winter outfit she’s styling today!

Win A $100 Payless Gift Card

Because they’re awesome, Payless would like to offer another $100 Gift Card to one lucky reader!!! Use the Rafflcopter widget below to enter the contest. You must be 18 years of age and have a U.S. mailing address. The contest ends on 12/23/16, and a winner will be chosen at random and notified by email within 48 hours. Good luck!

a Rafflecopter giveaway

This post was brought to you by Payless. Thank you for supporting the retailers that support this site. 

Join the Conversation

100 thoughts on “Cozy Casual Winter Outfit with Payless

  1. I love the outfit. I really enjoyed your 25 Days of Winter Fashion. Thank you and thank you also for all the great gift ideas.

  2. Ooooh! They come in Cognac too! Guess what is going in my basket right now! Thanks for finding a cute, lower priced option bootie! You look cozy!

  3. I love the sweater! I always forget how much taller you are than I am, so it’s a no go on me. Looks great on you though! Stay warm!

  4. You are the second person this week showcasing some goodness fro Payless. I haven’t popped into a store in quite sometime but I guess that needs to change.

  5. Great outfit! Now I have to go to Target and Payless. Yesterday I bought similar jewelry to what you had on. It was on sale at Lucky Brand.

  6. Love that cozy sweater! I’ve been meaning to stop by Payless ever since you featured them a couple of months back. Thanks for the 25 days series. It’s been fun!

    1. I tried 3 times with this one before I got it to look right. It does take some trial and error. 🙂 It’s not square, though, it is a large rectangle, so I just wrapped it around my neck and brought the ends in front. 🙂

  7. I have these boots in cognac and have been wearing them all fall. They are super comfortable and go with everything. Thanks for all that you do to keep us fashionable. Merry Christmas!

  8. What a stylish and warm winter outfit! I love the style collaborations you do with Cyndi. So many great ideas! And thank you for partnering with affordable brands like Payless. I had not shopped there in years until reading yours and Cyndis blogs. Since then I’ve purchased 2 pairs of shoes from there and 2 for my kids. And I’m hoping to get to an store soon to try on some OTK boots 😉

  9. Hi JoLynn, This is my first comment, although I have been enjoying your blog for a few weeks. I found it from the link on Cindy’s blog. You have both inspired me to try new clothing combinations. Thanks for helping me and lots of women like me to be able to get back into enjoying fashion again! Merry Christmas! Carrie

  10. Wow. Those shoes look great in the pictures. Interested to check them out in person. I just returned some Lucky brand shoes that looked exactly like them but didn’t fit right. Great outfit!

  11. Love everything about this outfit! I ordered those earrings for a friend. Hope she likes them! Thanks to you and Cyndi for your 25 days. Everything has been great!

  12. Really cute outfit! I haven’t shopped at Payless in years until you and Cindy started blogging about them. It made me stop and take at look at what they have and they have a lot of really cute shoes and accessories.

  13. I love the way you styled the scarf! I love the way scarves look on others, but they seem to add to my bust line. Will give this a try! Cute outfit on you!

  14. You weren’t kidding when you said these booties are selling out online! LOL. I hope to find them in my local store.

  15. Wow 25 days went by so fast. I loved every outfit and have picked up a lot of style tips and poses. I use to hate having my picture taken but now that I have seen the way you pose for the camera I don’t mind having my picture taken. Can’t wait to see whats coming on your next blog

  16. My 16-year-old daughter got a blanket scarf, and it looks so cute on her – and they always look great on you! Maybe I need to borrow hers and give it a try!!

  17. I love this outfit! It looks so cozy, something I’d definitely wear. I have those Payless booties in brown. I’m going to pull an outfit together based on your pieces here, in different colors. Thanks for the inspiration!

  18. I love this whole outfit!… The boots, the long cardigan, the blanket scarf… Going to work on duplicating it asap… Imitation is the sincerest form of flattery, right???… Thanks so much for all you do!… Merry Christmas!

  19. I love this look so much! I have searched for this sweater but had no luck and unfortunately it says it is unavailable to ship on their website. Oh well, at least I should have some success at Payless. Those shoes are adorable and look so comfy!

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