10 Midi Dresses to Wear in Windy Fall Weather

As a self-proclaimed “dress girl,” I often wear one, no matter the weather or occasion. As much as I enjoy feeling put together while wearing one of my favorite dresses, however, I don’t love having an accidental Marilyn Monroe moment when a gust of wind makes the hem of my dress fly up. Those embarrassing moments really counteract the effortlessly cool look I’m usually trying to strike when I’m traveling.

In the warmer months, my outfit rotation is full of cool linens and thin gauzy fabrics to help me beat the heat, but come fall, these ten dresses become my closet staples as they’re practically wind-resistant. These reliable dresses have me looking cute and trendy while still feeling comfortable and secure as I run around New York City, go apple picking upstate, and travel to Maine to attend a wedding. I’m so passionate about this topic that I scoured the internet for Travel + Leisure readers and found the ten best breeze-proof dress options, all for $50 or less. Don’t wait for your next embarrassing moment to score one of these great deals!

Best Dresses Overall

R.Vivimos Corduroy Midi Dress

This dress is made of 100 percent cotton, so it will be comfortable all day against your skin, no matter how windy and cold the weather may be. This V-neck, button-down dress features a removable belt so you can style it in more than one way: opt for a relaxed fit or cinch it for a more form-fitting look. Of course, we can’t forget to mention it has pockets for holding any essentials. The thick corduroy material will keep the hem of this dress from flying up around you on a windy day. Choose from an array of classic autumnal shades to find the perfect fit for you.

Quince Tencel Rib Knit Long Sleeve Dress

Although “day-to-night” outfits aren’t as popular as they once were, this Quince dress is a piece that can take you straight from the office to dinner. This lined long-sleeved rib knit midi dress comes in two sleek neutral shades that will be cohesive in any closet or travel wardrobe. As one reviewer says, the rib knit material is “ soft yet it hugs your curves,” meaning this dress won’t betray you if you’re out walking on a breezy day.

Old Navy Fit & Flare Sleeveless Denim Midi Dress

There really isn’t anything as reliable as denim in a closet—and that doesn’t just pertain to a pair of jeans. Small details of this denim dress elevate it from similar ones on the market. This includes the elegant square neckline, the secure wide stripes, and the seamed skirt that catches the eye. Available in two different washes, regular, petite, and tall lengths, and sizing that runs from XS to 4X, this dress is practically made for everyone. Currently on sale for just $35, it’s a comfy, versatile fall staple you don’t want to wait and miss out on.

Allegra K Dresses Sheath Dress

This dress will remain unmovable by any breeze with its sturdy suede-like material and form-fitting style. The sleeveless crewneck dress features a surprise split hem that adds a little excitement to an otherwise classic silhouette. This dress is also great for travel, because no matter how long it has been in your suitcase, it will remain wrinkle-free.

Caslon Ruched Cotton Midi T-shirt Dress

I adore throwing on one of my T-shirt dresses in the summer and instantly feel cool and casual, with little to no styling effort on my part. That’s why I instantly added this Nordstrom 100 percent cotton midi T-shirt dress to my cart as soon as I laid eyes on it, because it’ll provide the same ease for fall styling. The standout feature is the side ruching that not only gives a great shape to whoever wears it, but will help keep the dress in place in case they face any unwanted gusts of wind.

Saodimallsu Oversized Cable Knit Sweater Dress

Like a crisp white button-down and tall black leather boots, the classic sweater dress will never go out of style. The breeze stands no chance against the cozy fabric of this cable knit sweater dress. This buttery soft garment comes in six classic neutral shades, so you can easily find one that fits your existing wardrobe. One Amazon reviewer gave this dress a five-star rating because it can be “dressed up with a belt or just worn loose.” They go on to say they’ve worn it with everything from cowboy boots to a party to plain white sneakers for a casual dinner.

The Drop Claudia Cuddle Hoodie Midi Dress

When it’s a very windy day, I often wish I had my favorite sweatshirt with me to bundle up in. This cozy hoodie dress is the solution for all of those times I forgot to pack my just-in-case sweater, or I want a more casual look without looking frumpy. It also makes for a great travel-day outfit when you want to look styled, but still feel like you’re wrapped in your favorite blanket.

Old Navy Long-sleeve Twist-neck Midi Dress

Even though I love a nice sunny day, a dress like this makes me hope for colder weather just so I have an excuse to wear it. This showstopping long-sleeved midi dress features eye-catching keyhole cutouts by the neckline that add amazing visual intrigue to an otherwise standard dress. The slim-fitting style allows the wind to come and pass without any wardrobe malfunction incidents, and it can easily be styled with everything from tall boots to timeless slingbacks. 

Zoe and Claire Stripe Midi Polo Sweater Dress

Even as a certified dress girl, I have been loving the rugby shirt trend that has been across my newsfeed as of late. This polo sweater dress is a perfect way to translate the trend into something more dressy (literally), with its navy and white stripes and the cute, classic Johnny collar. Not only will this dress stay in place, but it will also keep you warm on a windy day.

Ebossy Women’s Boho Striped Shirt Dress

I love the look of a classic button-down, but often feel the way I style them never quite hits the mark. However, in dress form, this problem is solved! This striped shirt dress is great for all seasons, because you can keep some of the bottom buttons undone on a sweltering summer day for some air flow, or button them all the way down when the breeze is too much in the fall.

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