14 Romantic Dresses You Can Wear With Boots and Sneakers All Winter Long

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I, for one, love a romantic dress year-round, not just on Valentine's Day. Puffy sleeves, tulle, frills, a square neckline—I want it all. If it makes me feel like Buttercup from The Princess Bride or an Instagram ad for Reformation, I need it in my closet—stat. The cool thing about romantic-feeling dresses (which come in all styles, lengths, and levels of drama) is that they look especially good with a pair of sneakers. It's that high-low, prep-punk combination that makes the ensemble so good (and so fun)—not to mention it makes dressing up feel way more comfortable.

Below are a few of my favorite romantic, winter-ready dresses: Some definitely require tights (as well as perhaps a creative definition of "winter," but I tried!).

Best romantic dresses that look good with sneakers

baltic born mimi dress
Baltic Born Mimi Dress — $61.00

This is one of those easy dresses that will look good on you no matter what. I credit the gathered cinched-waist detailing and super stretchy material (a polyester-spandex blend). With a ~sexy~ V-neck and unique high-low hem, this is the kind of dress that makes you feel extra special. I like the burgundy color, but it’s available in four others, and sizes vary from small to 3XL.

madewell dress
Madewell Lucie Smocked Button-Front Midi Dress — $148.00

The Lucie style dress is one of Madewell’s bestsellers, and it’s easy to see why. It comes in different colors and lengths, but I love this on-the-long-side midi number that features a floral print that reminds me of the ’90s (in fact, if you’re not pairing it with a pair of Chucks, this would be stellar with some Doc Martens—channel your inner Juliette Lewis). The stretchy bodice gives you comfort, the buttons make it easy to put on and take off, and the cotton material is airy and breathable. We also stan a puff sleeve.

tanya taylor
Tanya Taylor Blaire Dress — $545.00

A Tanya Taylor bestseller, the Blaire dress is a classic, spring-y midi that features fluttery sleeves and an easy faux-wrap front that make it feel more casual. The slightly tiered skirt and tie at the waist make me feel like a present every time I wear it. Whatever shoes you choose to pair it with (I like to rock my white platform Keds), you’ll feel brighter and sunnier, thanks to the bold reds and pinks.

ava dress hill house
Hill House Home, The Ava Dress — $150.00

We recently wrote about how much we love Hill House’s new Victorian Romance collection, and we meant every word. While Hill House is known for its Nap Dress (also a romantic option!), we love the Ava Dress, which is part of the Victorian Romance collection, and equally gorgeous. This A-line dress has the ruffled shoulders the brand’s signature style is known for, but is cut shorter and has a wide V-neckline. You can snag it in this moody green floral, or a simple black. Both come with pockets (yay) and a matching belt.

Off White 3D Flower Mini Dress — $175.00

It’s hard to pick just one dress from Farm Rio , but this style is has me swooning. The easy breezy cut is elevated with the most thoughtful details, like 3D flower appliques, beaded tassels, and lace trim. Made of 100 percent cotton, the material is breathable and not at all heavy, which makes it perfect for spring and summer, too.


free people
Free People Violet Mini Dress — $108.00

And now, for a mini—because you can always wear it with some tights to keep you toasty. Plus, a mini dress looks ultra cute with some high top sneaks. The Violet’s long puffy sleeves and square neck and back make me want to call this a Babydoll Princess Dress, even though there is no such thing. I love it for its easy, pull-on style, but I’m also here for the textured fabric and variety of colors (if you don’t like this dark orange, you can go with eight other options).


Valani Sodalin Hemp Midi Dress — $298.00

Another poofy sleeve dress, but this time it’s got a baby V-neckline, a slight neck ruffle that makes me believe Queen Elizabeth would wear this in 2022, and puffed shoulders that aren’t too much. Aside from how pretty this dress is, it’s also made of a plant-based material that’s both hypoallergenic and temp-regulating, so you can wear it year-round. To top it off, it comes with an attached waist belt you can tie in a gorgeous, versatile bow.


lisa says gah
Lisa Says Gah Nev Slip Dress, Mariposa Black — $158.00

Be the main character of the ’90s movie of your dreams with this butterfly-adorned mini slip dress. Yes, you’ll need tights and a coat or hearty cardigan during winter, but it’s all worth it: As soon as you walk into the room, everyone will be asking where you got this fit. Made of a polyester-recycled satin blend, it’s buttery soft and super workable around your wardrobe.

Reformation Sigmund Dress — $248.00

Sometimes, all you need is an intense square neckline to feel like an extra from Ever After—in the best possible way. With long sleeves and slightly puffed shoulders, this Reformation dress just feels special. Made from a more sustainable viscose and rayon blend, the Sigmund Dress has features like a high slit so you can show some leg, and elastic at the cuffs and shoulders so it doesn’t feel stiff. Plus, it plays nice with strapless bras.

Eloquii Surplice Bodice Pleated Dress — $140.00

The hot pink! The ruffle details! The smocked waistband! The oh-so-smart A-line pleated skirt! There’s so much to love about this dress (those slightly billowy sleeves? Gimme). This midi dress (it hits below the knee) is just flowy enough to ensure comfort and an easy fit. Made of polyester, it’s lightweight and pairable with jackets and your favorite sneaks or boots.


astr the label
ASTR The Label Puff Sleeve V-Neck Back Cutout Midi Dress — $89.00

If you’re not afraid of a little shoulder drama, this dress has got what you need. Puffed shoulders, ruched cuffs, a deep V-neck, and gorgeous back cut-out makes this ensemble a keeper. It comes in black floral (pictured), and purple-peach floral (not pictured, but it makes us think of a field of lilacs in outfit form).

good american
Good American Scuba Midi Dress — $99.00

This classic bodycon dress is named “scuba” after its scuba fabric, which is meltably soft and comfortable. This is the kind of dress I’d wear out to a Nice Dinner, but it’s one that can be easily dressed up or down. Dress it up with some heels and jewelry, dress it down with a leather jacket and your Fila sneakers. Brownie points must be awarded to the adjustable spaghetti straps. Good American can always be relied on for thoughtful design.



Tucker Allyson Dress in Silk — $475.00

Tucker is another brand that makes it very hard to pick just one thing. Thanks to their interesting shapes, comfy fits, and best-in-class materials, the brand’s dresses feel unique. The Allyson shirt dress is a favorite thanks to its silk makeup and arty pattern (it comes in nine prints with fun names like “Purple Punch,” and “Amber Tiger”—this one is called “Baroque Floral” which is perfect). Features like secret pockets and front zips are just the cherry on top.


Amanda Uprichard Theodora Dress — $251.00

A list of romantic dresses wouldn’t be complete without some tulle and more appliques. This floral goth babydoll dress has the sweetest square neckline and see-through puffy sleeves. To add more flair and theater, it stars a tiered skirt that will definitely make you want to do a princess spin (just make sure you’re wearing shorts, leggings, or are just fully aware everyone will see your butt). Made of polyester, you’ll just want to get this one dry-cleaned (the washer is a known enemy of tulle).


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Our editors independently select these products. Making a purchase through our links may earn Well+Good a commission.

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