The Dress Edit

Maxi Winter Dresses For A Stylish Cold-Weather Closet

@HANNAHARTWEAR / INSTAGRAM

Maxi Winter Dresses For A Stylish Cold-Weather Closet

With the cold-weather plans stacking up fast, our need for stylish maxi winter dresses is greater than ever! Of course, dresses that not only look ultra-stylish but keep us warm in the process can seem like a rare find. Luckily, we’ve done the hard work for you and put together an edit of irresistible pretty, fashion-forward dresses that’ll instantly elevate your cold-weather closet and have you feeling your best and most stylish self all season long. So keep scrolling, below you’ll find 30 must-have dresses from Free People, DVF, Boden, Etro, Anthropologie, and more!

Hemant & Nandita

@johannaortizofficial / Instagram

Maxi Winter Dresses From Day To Night

Thought maxi winter dresses were only for your daytime plans? Think again! Just a quick peek at our selection and you’ll see just how many of the dresses on our list can easily be dressed up or down depending on the dress code! For example, the Janeti tiered dress by Ted Baker London has day to night written all over it. Style this chic printed dress with heeled boots for effortlessly chic off-duty vibes this winter. Alternatively, opt for heels when the rsvp calls for a slightly dressier ensemble!

Meanwhile, who wouldn’t love adding the Hanging Garden maxi dress by Johanna Ortiz to the winter collection? This stunning silk-satin creation is undeniably pretty and incredibly elegant to boot. Additionally, the luxurious shade of deep burgundy punctu\ated so perfectly with the off-white floral print was made for this time of year. Once again, this dress will look just as good with heeled boots as it does with heels making it a must-have for every plan on your winter calendar!

  • BERNADETTE Mathilda Floral Velvet Bow Maxi Dress

    $990
  • HEMANT & NANDITA Rafa Georgette Floral Maxi Dress

    $515
  • JENNY YOO Stretch-Velvet Brown Sabrina Dress

    $298
  • THE SOMERSET Chiffon Maxi Dress

    $170
  • ANTHROPOLOGIE Burnout Velvet Dress

    $230
  • FREEPEOPLE Lennon Dress

    $168
  • FREEPEOPLE Dahlia Maxi Dress

    $350
  • FREEPEOPLE Colette Maxi Dress

    $400
  • FREEPEOPLE You’re A Jewel Printed Maxi Dress

    $198
  • FREEPEOPLE Hollis Dress

    $198
  • FIL DE VIE Beatriz Tiered Silk-satin Maxi Dress

    $770
  • THE VAMPIRE’S WIFE The Festival Jumbo-cord Maxi Dress

    $887
  • ETRO Rebecca Leopard-print Silk Dress

    $4,527
  • FREEPEOPLE Calloway Dress

    $198
  • ANTHROPOLOGIE Smocked V-Neck Maxi Dress

    $248
  • FAVORITE DAUGHTER The Favorite Dress

    $218
  • SIDDHARTA BANSAL Long-Sleeve Maxi Dress

    $220
  • ULLA JOHNSON Emi Mixed Print Tiered Silk Dress

    $1,195
  • VINCE Lilac Floral Print Pleated Dress

    $595
  • TED BAKER LONDON Janeti Tiered Long Sleeve Dress

    $395
  • ASOS DESIGN Floral Embroidered Long Sleeve Maxi Dress

    $134
  • BODEN Floral Print Tiered Cotton Dress

    $198
  • RAEY Tulip-print Drawstring Jacquard Dress

    $552
  • HOUSE OF HARLOW 1960 x REVOLVE Francia Maxi Dress

    $298
  • BA&SH Ginger Maxi Dress

    $495
  • ADAM LIPPES Pleated Floral-print Silk-chiffon Maxi Dress

    $2,890
  • JOHANNA ORTIZ Hanging Garden Printed Silk-satin Maxi Dress

    $1,995
  • DVF Akil Maxi Dress

    $358
  • HANNAH ARTWEAR Rio Open-back Cutout Floral-print Georgette Maxi Dress

    $495
  • THE SOMERSET Maxi Dress

    $168

Maxi Winter Dresses To Pretty To Pass Up

When it comes to the prettiest maxi winter dresses of 2022, we’ve been truly spoiled for choice. For example, with Favorite Daughter’s The Favorite dress. Aptly named, this maxi will be top of our to-buy/to-wear list this cold-weather season and it’s clear to see why. Firstly, this dress demands attention with its deep red, black, and gold leaf print. Secondly, its silky slip design makes it perfect for layering under knitwear for a cozy daytime look. However, it’ll look just as amazing with a leather jacket, and heeled black leather boots or heels for the evening. Add this to your cart now before it inevitably sells out!

Additionally, we’re head over heels for the Rio open-back cutout maxi by Hannah Artwear. As chic as it is beautiful, this dress stuns from every angle. Not to mention, we can’t get enough of those sultry waist cut-outs, long sleeves, and the autumnal shade of salmon pink!

Shop All Maxi Winter Dresses

Free People

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