dress: & Other Stories (c/o) | coat: vintage, similar here | earrings: Machete (similar here) | boots: Stuart Weitzman, similar on major sale now! (similar and more affordable here)
I love receiving feedback from you guys on Instagram. Recently I’ve had a lot of comments and DM’s about my dresses more than anything else. I had a male follower (which I don’t think I have many!) send me a DM saying that dresses better suit me and that I should wear them more. Thanks, I think, and I do enjoy wearing them.
Another one of you said that “no one can pull off a maxi like you can.” I also think I’ll take that as a compliment and think it’s one of my favorite silhouettes—when done right. I didn’t realize how much I do love a maxi until this comment. It’s kind of the easiest thing to wear and you don’t have to wear pants or shave your legs. Win, win right?
Here’s the thing, you totally can pull off a maxi dress. I know a lot of you petite women are saying, ugh I can’t pull it off though. Here me out. YOU CAN TOTALLY PULL OFF A MAXI DRESS. You can get it hemmed or better yet, shop for a MIDI-DRESS (tea length), which is what the one I’m wearing here is considered (I’m 5’7″ for reference).
Maxi dresses are an easy thing and kind of a no brainer for the summer months, right? I’m sure many of you already own some summery ones in your closet, but how many of you think to wear them all year long? Maybe it’s because you never thought to wear one or knew how to stay warm wearing a maxi dress in the winter.
Well here are my tips on how to wear a maxi dress when it’s cold out:
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pair it with over the knee boots like these are basically like wearing pants and keep you so warm
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layer with heat tech tights and seamless shapewear
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layer with a turtleneck underneath
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throw a chunky sweater over it
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layer it with jeans (you totally can and I did it here!)
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Want more inspo? Check out two of my friends, Laura and Jenny who also rock a maxi dress all year long so beautifully.
Now that you have some ideas, go stock up on my favorite maxi / midi dresses from the shop I’ve been obsessed with, & Other Stories, which is H&M’s sister company that is designed by ateliers in LA, London, Paris and Stockholm so it’s like shopping in a boutique with affordable prices.
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photos by Rima Brindamour
FAQs
Can you wear a maxi dress in freezing temperatures?
Yes, but comfort should always come first. The key is adapting your outfit to your climate and daily activities. On especially cold days, you may need additional layers or warmer accessories.
What shoes should I wear with a maxi dress in cold weather?
Boots are one of the best options for styling a maxi dress in the winter. Knee-high and over-the-knee boots add warmth without disrupting the silhouette. They also make the outfit feel more seasonally appropriate.
How do I stay warm in a maxi dress during winter?
Layering is the secret. Tights, thermal layers, sweaters, and jackets can help make a maxi dress comfortable even on colder days. The right layers allow you to wear your favorite dresses longer throughout the year.
Can I wear tights under a maxi dress?
Yes, and they’re a great way to add warmth without changing the look of your outfit. Depending on the weather, you can choose lightweight tights or warmer thermal options. Most of the time, they’ll stay hidden under the dress.
What jackets look best with maxi dresses?
Structured jackets, leather jackets, and tailored coats all pair beautifully with maxi dresses. The best choice depends on the style of the dress and the occasion. A jacket can also help add shape and polish to your outfit.
How do I layer a sweater over a maxi dress?
A sweater can completely transform a maxi dress. It creates the look of a skirt and sweater combination while giving you more outfit options. This is one of the easiest ways to get more wear out of a dress you already own—and exactly the kind of styling trick we uncover during The Closet Refresh®.
Are maxi dresses flattering in the winter?
Yes. Maxi dresses create a long, streamlined silhouette that works well year-round. Thoughtful layering helps maintain shape while keeping you comfortable.
Can I wear a floral maxi dress during colder months?
Definitely. Floral prints aren’t limited to spring and summer. Pairing them with boots and cozy layers can make them feel perfectly appropriate for fall and winter.
How can I make a maxi dress look more seasonal?
Accessories can make a big difference. Scarves, boots, jackets, and textured fabrics instantly help a maxi dress feel more suited to colder weather. Small styling changes can completely transform the look.
What are the best layers to wear under a maxi dress?
Lightweight thermals and fitted basics work well under most maxi dresses. They provide extra warmth without adding bulk. This makes them ideal for colder days.
Can petite women wear maxi dresses in winter?
Absolutely. The key is finding the right length and paying attention to proportion. Adding heeled boots or defining the waist can help create balance. If you’re still figuring out which silhouettes work best for you, my Find My Style Quiz is a great place to start.
How do I style a maxi dress for everyday wear?
Keep it simple and comfortable. Pair it with a cardigan, denim jacket, or ankle boots for an easy everyday outfit. Maxi dresses can be one of the most versatile pieces in your closet.
How many ways can I style one maxi dress in winter?
More than most people realize. Small changes to your shoes, outerwear, accessories, and layers can create completely different looks from the same dress.
Are over-the-knee boots a good choice with maxi dresses?
Yes. They provide extra warmth and often remain hidden under the dress. They’re a practical option for staying comfortable in colder temperatures.
Can I wear a maxi dress to work in the winter?
A maxi dress can be a great workwear option when styled thoughtfully. Adding a blazer, structured coat, or polished accessories helps create a professional look. It’s an easy way to stay comfortable while looking put together.
What’s the biggest mistake people make when styling maxi dresses in cold weather?
Many people assume maxi dresses are only for warm weather. With the right layers, they’re actually one of the easiest pieces to transition into winter. Don’t be afraid to experiment with sweaters, jackets, and boots.