Winter Dresses and Boots from Free People

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When it comes to styling winter outfits, the options are endless. Although I love a classic look with highwaisted jeans & a sweater, every once and a while it’s fun to pair my favorite maxi dresses with boots and a jacket. Free People has always carried an amazing selection of winter styles with high-quality pieces and versatility to fit everyone’s style preferences! Their dresses, jackets and boots have always caught my eye and play a key role in all of my favorite winter styles.

Winter Dresses and Boots from Free People

1. I love the vibrant pattern and colors on this FIRST DATE MAXI DRESS. The fit is perfect for layering with a cute blazer or jacket.
2. I’ve ordered this DOLMAN QUILTED DUVET COAT and love everything about it. Such a pretty, soft and warm winter coat!
3. This WANDERER CARDI DRESS has the cutest, relaxed fit. Love the slouchy style and options for dressing it up or down. Also super cute to wear with some combat boots.
4. These DR. MARTEN JADON LACE-UP BOOTS have the best, chunky style and are perfect for styling in the winter. In fact, I love wearing mine with dresses or jeans.
5. Love the ruched waist and balloon sleeves on this PRARIE PUNK SHIRTDRESS! All 3 pattern options are so cute and perfect for accessorizing and layering in the winter. 
6. Such a cute mix of denim details and shearling on this LEVI’S PIECED TRUCKER JACKET! I also love the fun design and styling options.
7. The tiered silhouette and puff sleeves on this SWEET ESCAPE MAXI DRESS are the cutest details! Such a flattering style and so easy to pair with your favorite booties.
8. These ELLE BLOCK HEEL BOOTS look so fun to style and dress up with a printed maxi and cozy jacket.
9. I love the sherpa material this IZZY WRAP TEDDY JACKET is made of. The oversized lapels are such a cute detail and all 5 colors are also great for the winter.
10. This ASHBY BLAZER is such a fun styling piece and perfect for layering with a fitted dress and boots. Love the subtle plaid print and length.
11. Love the western style of these VEGAN DALEY ANKLE BOOTS. They also come in a black and white option and hit at the perfect height for a casual outfit or more dressed-up look.
12. This VEGAN LEATHER MOTO JACKET is such a fun styling piece and great for wearing with dresses or jeans and boots.
13. Love the simple style of these DAKOTA HEEL BOOTS. 7 colors to choose from and also a timeless style.
14. This EDIE DRESS comes in a pink, white and grey color option. The flowy style is so beautiful and great for pairing with a denim jacket & boots.
15. I love all the styling options you can get with this WALK ABOUT MAXI DRESS. Such a comfortable sweater material that’s so easy to layer or wear on its own.
16. The balloon sleeves on this LEVI’S TRUCKER JACKET are the cutest details. Denim jackets are the best for all seasons and look so cute worn with dresses.
17. There are so many beautiful details in this ADVENTURING MIDI DRESS. Such a pretty, neutral color and also perfect for pairing with your favorite sneakers, boots or sandals.
18. I love the paisley prints this BILLIE JACKET comes in. The faux shearling liner looks so comfortable!
19. This LYDIA PRINTED MIDI DRESS comes in 2 vibrant print options and is a great dress to wear through any season! Love the spunky floral and puff sleeves.
20. Such a cute cropped, relaxed fit on this GEORGIE JACKET. Love the bomber style and removable shearling collar.
21. I love the tiered ruffles on this SYD POPLIN MIDI DRESS. Perfect for pairing with a denim jacket and booties for a winter outfit.
22. The plaid and shearling details on this AZALEA MENSWEAR JACKET play such a fun twist on the classic trucker style. Such a cute fall & winter jacket.
23. I love the knit sweater material and v-neck on this G2G MIDI DRESS. Both color options are so cute and perfect for winter styling.
24. I love the terry fabric and shirt style of this NOMAD SHIRT JACKET. There are 3 cute colors to choose from and so many great ways to style it.
25. Such a cute slouchy style on these SUTTON TIGHT BOOTS. There are 5 great colors to choose from and the design is comfy and easy to style!