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3 Cute and On-Trend Hats for Dresses to Add to Your Collection This Fall

Fall is the season of hats. During the summer, hats are (mostly) practical. During the fall, however, hats strike more of a balance between practicality and style. You can wear all sorts of hats—some brimmed, some not. It’s all about matching your hat to your outfit. If you’re wearing more dresses in the fall, you may want more hats that work with those dresses. Here’s a look at a few cute and on-trend hats for dresses you’ll want to add to your wardrobe this fall. You may even have some of these hats in your collection already. Either way, it’s time to get your hat on.

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A Baseball Cap for Every Dress—and Occasion

Snapback, adjustable, fitted, dad cap, flat brim, trucker—you name it, caps come in all kinds of styles beyond the traditional “baseball cap.” This hat category gives you many options with subtle style variations. No matter what baseball cap type you wear, you get a surprisingly versatile silhouette. You can wear it forward or backward. A backward baseball cap looks très chic with a dress. Or you can wear your hair down and flowing from under the cap. Thanks to the brim and adjustability of most caps, keeping your hair and bangs out of your eyes is easy. Of course, you can always go with the classic ponytail through the back. That’s a look that makes caps one of the top hats for dresses.

Pairing your cap with your dress is where things really get fun. A floral embroidered design on the cap paired with a floral dress? Oh yeah. Or maybe some embroidery to show local pride or team colors. With professional and collegiate football in full swing, many people show their support by donning their favorite caps. Many teams have introduced cap designs in colors and embroidered patterns that work remarkably well with dresses. So, you can wear that flowy number with your team front and center on your cap. It’s a fall look that isn’t going anywhere anytime soon.

Wide-Brimmed Hats Are the Perfect Fall Hats for Dresses

Like baseball caps, wide-brimmed hats come in various styles and colors. The Panama hat is a prime example. It’s often considered a summery hat because it pairs well with so many summer fits. But it’s a great hat to carry over to fall because, as you might have guessed, Panama hats are ideal hats for dresses no matter the time of year. You can wear them casually or dress them up. A felt Panama hat with a colored band works especially well with floral maxi dresses and boots.

Another thing that makes Panama hats great for fall is that they’re structured. During the summer, you might wear a floppier, ultra-wide-brimmed hat for lounging by the pool or at the beach. But during the fall, you might want something more structured with a slightly narrower brim and made with a material that works better in cooler weather, like felt.

From the 1920s to the 2020s, Cloche Hats Are Must-Have Fall Hats for Dresses

Cloche hats are the way to go if you’re looking for something a little different this season. These are must-haves hats for dresses during the fall. The narrow brim and bell shape makes it a stellar addition to your dressy look. They work with maxi and midi dresses. They aren’t the most common, but they’re a worthy addition to your fall collection—and worth seeking out. And they’re undoubtedly retro. As in early 1900s retro—cloche hats were popularized in the 1920s. Then, they often had a floppy kind of look. These days, while you can still get that floppy brimmed style, you can get more structured cloche hats, too. A structured hat with a maxi dress is a look that’s quintessentially fall.

About Dress Up

Dress Up isn’t your typical clothing boutique. They’ve taken the clothes shopping experience and turned it into something memorable and exciting. When you visit Dress Up online or in-store, you’ll discover over 60 new looks across their lines 2-3 times weekly. Why the rotation? Dress Up founders Derrick and Danielle Case know how hard it is to find affordable and on-trend styles. Shopping for new styles shouldn’t be boring. So, they created a way to stay ahead of the curve and deliver a clothing experience you won’t find anywhere else. Explore their website for dresses or stop by any of their 16 stores across the Southeast for the latest cute tops, dress shorts, denim, hats for dresses, accessories, and much more. What will you discover this week at Dress Up?

Create a new fall look with hats for dresses at https://shopdressup.com/

Isabella Ramos

I’ve been interested in fashion for as long as I can remember, and I’ve been writing about it professionally for many years. Whether it is cute outfits for brunch or that perfect cocktail dress for a girls' night out, I think what you wear is reflective of so many things in life. I love helping others see the fun they can have in expressing their individuality. While I certainly have my favorite brands, I enjoy sharing my knowledge of fashion across all levels of the industry. Thank you for checking out my profile!

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