How to Style Maxi Dresses in Colder Weather

Photography by Taylor Cole Photo

Outfit Details:

Brigitte Bailey Maxi Dress, Old Leather Jacket (Similar Here under $100), Born Ankle Boots, Tory Burch Bag (on sale for 30% off!)

Maxi dresses are one of 2017’s biggest dress trends, and although I haven’t been into maxi dresses for the past few years, I’m suddenly back on the wagon and obsessing over them. The key for me is the right silhouette and fabric — a lightweight chiffon or rayon makes for the prettiest drape and movement as you walk.

As they’ve been showing up in stores, I’ve had a few questions about how to style them in the cold weather, because typically we see them in the summer with sandals or wedges. So today I’m sharing a few ideas to styling them during the colder months. And although the winters are obviously more mild here than some places, the same styling principles can apply if you’re styling for super cold weather.

Here are a few ideas for styling those maxi dresses in colder weather:

  1. Try darker colored maxi dresses. A black, gray, deep purple, or navy colored dress will instantly feel more winter appropriate, and will be easier to pair with winter accessories and layers.
  2. Pair your summer dresses with winter-y pieces. If you have a summer-y maxi dress, you can often still wear it during the colder months! Just pair it with a season appropriate layer and shoes. A black leather jacket is often a great way to add an unexpected edge and contrast to a summer-y piece, or a suede jacket, like this one, is another good option. Just make sure the combination feels purposeful, rather than just like you threw your winter coat over a summer dress. If your dress is too summery, just put it away and pull it out in the spring.
  3. Pair with the right outerwear. Of course a jacket, coat, or cardigan is a necessity for layering in the winter, but remember that a floor length dress is going to change your proportions so they’re different than normal. Here’s how to compensate: Try a cropped jacket, like this one or this one, or for colder weather, a cropped coat like this one or this one. The shorter length will help accentuate your waistline so it doesn’t get lost in bulky outerwear. If you choose a cardigan, longer hip length cardigans are great. And add a hat if you’d like to make the outfit feel more season appropriate.
  4. Wear the right shoes. During the winter, you obviously need your toes covered up. Choose a sleek pair of ankle boots like these, or a fitted pair of tall boots, like these.  Don’t wear bulky boots like these.
  5. Keep your legs warm. If you need some extra warmth, wear leggings or tights underneath your dress. If your dress has a slit like mine, stick to tights only — no random bare ankles sticking out of your beautiful dress!
  6. Try a slightly shorter length. If you struggle with maxi dresses, try an ankle length dress, like this one. Pair them with a thin and fitted boot, like this one or this one. With those ankles exposed, you want them to be as narrow and thin as possible so your feet and legs don’t look bulky and disproportionate.

I’ve linked up some of my favorite maxi dresses below!

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  1. Natali says:

    You’re looking absolutely breathtaking! Gorgeous woman in an impressive maxi dress!

  2. Paige Cassandra Flamm says:

    That dress is gorgeous! And I love it paired with the leather!


  3. Sarah says:

    I’ve always loved maxi dress because I don’t always love shaving my legs! Also, with a great pair of wedges, they make me look taller than 5’1″. Ready for spring time and dress!

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