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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
- 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.
- I’ve ordered this DOLMAN QUILTED DUVET COAT and love everything about it. Such a pretty, soft and warm winter coat!
- 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.
- 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.
- 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.
- 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.
- 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.
- These ELLE BLOCK HEEL BOOTS look so fun to style and dress up with a printed maxi and cozy jacket.
- 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.
- 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.
- 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.
- This VEGAN LEATHER MOTO JACKET is such a fun styling piece and great for wearing with dresses or jeans and boots.
- Love the simple style of these DAKOTA HEEL BOOTS. 7 colors to choose from and also a timeless style.
- 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.
- 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.
- 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.
- 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.
- I love the paisley prints this BILLIE JACKET comes in. The faux shearling liner looks so comfortable!
- 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.
- Such a cute cropped, relaxed fit on this GEORGIE JACKET. Love the bomber style and removable shearling collar.
- I love the tiered ruffles on this SYD POPLIN MIDI DRESS. Perfect for pairing with a denim jacket and booties for a winter outfit.
- 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.
- 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.
- 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.
- 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!