Maxi Winter Dresses For A Stylish Cold-Weather Closet


The Dress Edit

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!

Maxi Winter Dresses For A Stylish Cold-Weather Closet

Hemant & Nandita

Maxi Winter Dresses For A Stylish Cold-Weather Closet

@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!

Shop more dresses selected and reviewed by our expert fashion buyers and stylists

  • KHANUMS Pearl And Gold Bead Detail Keidi Dress

  • JENNY PACKHAM Georgia Crystal-embellished Sequined Tulle Gown

  • NBD Daphne Maxi Dress

  • ALESSANDRA RICH Polka-dot Silk Crepe Midi Dress

  • NERVI Naomi Draped Ruffled Cutout Crepe Maxi Dress

  • MIGUELINA Emilline Belted Lace-trimmed Cotton-gauze Maxi Dress

  • HOUSE OF CB Lavele Long Sleeve Crepe Dress

  • ALEXANDER MCQUEEN Chiaroscuro Floral-print Shirt Dress

  • THEMIS Z Aelia Abstract-print Silk-velvet Kaftan Dress


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

Maxi Winter Dresses For A Stylish Cold-Weather Closet

Free People

Maxi Winter Dresses For A Stylish Cold-Weather Closet

Jenny Yoo

These Halloween Designer Dresses Are So Chic It’s Scary