7 Hat-Friendly Long-Sleeved Dress Styles to Wear in the Winter

Winter is here, and you want to bring out your warm and cozy knits and sweaters. But why not show off your winter style with something a bit different this season? Long-sleeved dresses are stylish and incredibly comfortable, making them the perfect wardrobe staples for the cold months ahead.

These wardrobe staples can be styled in many different ways. With the addition of cute hats for women, you can create an effortless winter look that looks amazing and also keeps you warm.

Winter is the perfect time to break out the cozy sweaters and fedoras, but sometimes it can be difficult to put together stylish yet warm outfits. Don’t let the chill in the air stop you from looking stylish! We’ve rounded up 7 of the long-sleeved dress styles to get you through the winter, and they can be easily styled with any type of hat.

How to Style Long-Sleeved Dresses with Cute Women’s Winter Hats

The winter season is a great time to experiment with your fashion style. One way to do this is by styling long-sleeved dresses with hats. This combination creates an edgy, fashionable look that is perfect for the cold weather.

When styling them with winter visors, there are several options to choose from. For instance, adding a long sleeve shirt underneath a dress will turn a short sleeve or sleeveless dress into a winter-ready style.

Layering it with a chunky knit or scarf is another popular winter styling option. Adding a blazer or a more polished jacket to jeans can create a dressier winter look that pairs nicely with different types of hats for women.

No matter which style you choose, accessorizing with the right hat can be the icing on the cake. Whether it is a fedora, beanie, or baseball cap, find one that matches your outfit and expresses your unique and stylish looks this winter!

We know that winter fashion doesn’t have to mean sacrificing style for comfort. Here are 7 of our favorite long-sleeved dress styles that you can easily pair with Chanel winter hats for an on-trend winter look. Keep reading to find your next winter outfit!

The Denim Long-Sleeved Dress with a Fedora

Denim dresses, from the classic button-down to long-sleeve chambray to a boxy cut, are the perfect winter go-to. To dress up the denim dress, you can add a Fedora hat for a look that has a classically cool feel. The combination of denim and a Fedora hat is ideal for just about any occasion. Whether you’re attending a wedding or running errands on the weekend, this look is for you.

Not all denim dresses need to be basic, either. For an edgy winter look, try out the long-sleeved Wrangler denim dress with trims and fringes. If you want something more fashionable and casual, the Country Halter Chiffon Dress might be the best choice for you. It has a girly hemline and a unique strappy design.

To add some sophistication for night outs or special events, Rod’s Sexy Black Lace Long-Sleeved Dress will be your ladies’ go-to. It has a soft lace fabric and keyhole back detail. No matter which denim dress you choose, it is sure to give your look that extra oomph. This look will be extra cool with a touch of style when it’s coupled with a Fedora hat this winter!

The Turtleneck Long-Sleeved Mini Dress and Beanie

The next style of winter dress and hat combo is the turtleneck long-sleeved mini dress and beanie. This look has become quite popular in recent years, showing up on Pinterest boards and Instagram feeds alike.

The fitted turtleneck dress not only provides the necessary insulation to keep you warm in the winter but can be effortlessly layered over jeans or leggings. This look gives further warmth, depending on how cold it gets.

Pair this ensemble with a fashionable beanie or any cute women’s hat to prevent your ears from freezing in cold weather. This style can also be styled with over-the-knee boots for an edgy, bold look that will have you turning heads.

The versatility of this outfit makes it perfect for traveling—you’ll never feel overdressed and you’ll stay comfortable too!

The Long-Sleeved Wrap Maxi and Wide-Brimmed Hat

If you are looking for a dramatic, chic look, then the long-sleeved wrap maxi is your go-to piece. This look is simultaneously classic and modern. Whether it’s plain or printed, fitted or loose, the long-sleeve wrap maxi can be dressed up for a night out with the girls. You can also wear this for a casual brunch date.

Paired with cute wide-brimmed women’s hat and heeled sandals or boots, you’ll be sure to turn heads this winter. The combination of long sleeves and the wide-brimmed hat will keep you warm and make you look effortlessly chic in any setting.

The Long-Sleeved Velvet Midi and Fascinator Hat

The long-sleeved velvet midi dress is a luxurious and chic addition to any winter wardrobe. This style is perfect for either formal or semi-formal events and can be easily styled with accessories.

The velvet midi dress can be worn with a fascinator hat to add a bit of class. Fascinators are eye-catching hats that often feature feathers, beads, and sparkly details. Wrist-length gloves in black or ivory are an excellent choice for a more formal occasion.

A pair of boots or heels can complete the look for less formal events. When wearing this kind of outfit, don’t forget an elegant shawl or wrap to keep yourself warm!

The Long-Sleeved Knit Sheath and Newsboy Cap

For a fashion-forward look, consider layering a dress with a long-sleeved knit sheath and topping it with a newsboy cap. This style is perfect for winter as it pairs the warmth of a knit top or cardigan with one of the seven styles. The added warmth of this layering effect will ensure the wearer looks stylish and stays cozy all season.

The newsboy cap perfectly completes this look, adding an extra layer without taking away from any part of the outfit. For those in colder climates, the newsboy cap can also provide some insulation against wind and snow while keeping your head warm. The newsboy cap has a wider brim than other hats like beanies and fedoras. It allows enough room to keep your catchy hairstyle underneath if you like wearing your hair down.

This layered look can be dressed up or down, depending on how formal or casual you’d like to be. It can be styled for any occasion or event during the winter season. Whether it’s a meeting, holiday celebration, or just running errands, this pairing of a long-sleeved dress plus a knit cardigan and a newsboy cap is sure to get you noticed while keeping you warm!

The Long-Sleeved Tunic Dress and Beret

The long-sleeved tunic dress and beret combo are a classic winter style. The tunic dress is a semi-structured but simple piece that hugs the body nicely. It may look simple, but it can be dressed up with the right accessories. A beret and some chunky jewelry can elevate the look.

Wearing a long sleeve shirt underneath will give you extra warmth, just like the Margot 2-in-1 dress. When you’re rocking this winter look, layer your clothing for added warmth. A sleek black turtleneck would go well with this outfit!

A Bold Long-Sleeved Floral Dress Paired with a Cute Women’s Winter Hat

Winter doesn’t mean you can’t sport a flowery look. A long-sleeved floral dress paired with cute women’s winter hats is a bold and stylish way to show off your style this season. Floral prints are always in, making them the perfect addition to your winter wardrobe.

They also come in all sorts of colors and patterns and can be dressed up or down depending on the occasion. When paired with bulky, cute winter hats for women, you’ll have an outfit that’s sure to turn heads.

If you’re looking for something edgier, try pairing your dress with a wide-brimmed fedora or floppy hat for a chic and sophisticated look. If you’re going for something more subtle, try sporting a beanie or felt hat. These combinations are sure to keep you warm without sacrificing your style.

Whatever type of floral print long-sleeved maxi dress you choose to wear in the winter season, there are endless ways to style it with a winter hat. So don’t shy away from the bold look, and be sure to rock it this season!


With winter well and truly here, it’s time to switch up your wardrobe and ensure you’re ready for the cooler weather. Investing in a few of these long-sleeved dress styles is a great way to layer up and add some chic style to your winter outfits.

For an extra touch of style, adding a cute women’s winter hat to your ensemble is a great way to keep warm and look fashionable. Whether you’re a fan of beanies, fedoras, or cloches, there is a range of hats that you can style with your long-sleeved style dress for a stunning winter look. So don’t forget to grab your favorite hat and embrace winter in style!

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