15 Fun and Cute Dresses for Winter 2024

Shades of wine, orange, yellow, and brown – those are the typical colors when you think of the winter season. But this doesn’t mean that you have to stick to this color palette over and over just because it’s winter.

Repeatedly wearing the same colors might make you look like you’re wearing the same thing every day, so better spice things up a bit and broaden your color palette, whether it be adding a new color or pattern. Don’t know where to start? Don’t worry; we’ve got you covered. Here’s a list of dresses that we recommend you try.

Photo: macys.com

Women’s Sleeveless
Keyhole Back Maxi Dress

View at Macy’s | $69 $27.53

When looking to refresh your dress options, Vince Camuto’s creation stands out. Its unlined construction imported quality, and flattering below-the-knee length make it a fantastic addition to your wardrobe rotation this season.

Price at the time of publishing: $69 $27.53

Brand: Vince Camuto | Sizes: XXS | Colors: N/A

Photo: macys.com

Studded Illusion
Choker Sheath Dress

View at Macy’s | $229

Xscape presents a truly memorable ensemble with their body-contouring sheath dress adorned with faceted stud work, adding a touch of texture and radiance. This boasts illusion beaded sleeves and sides, along with a concealed back zipper for a seamless finish, featuring a chic mock neck with a keyhole and a flattering sheath silhouette.

Price at the time of publishing: $229

Brand: Xscape | Sizes: 4 to 16 | Colors: Black/Nude/Silver

Photo: jcpenney.com

Robbie Bee Petite
3/4 Sleeve Sheath Dress

View at JCPENNEY | $69 $55.20

This Robbie Bee sheath knee-length dress is a standout piece from their women’s petite collection. The abstract pattern injects a burst of vibrant color into your wardrobe. Featuring a crew neckline, three-quarter sleeves, and a flattering gathered waist detail, it’s designed to highlight your silhouette effortlessly.

Price at the time of publishing: $69 $55.20

Brand: Robbie Bee | Sizes: Petite S to Petite XL | Colors: Black Red

Photo: macys.com

Women’s Sequined-Mesh
Sleeveless Shift Dress

View at Macy’s | $128

Absolutely stunning, this Kensie dress boasts a timeless beauty with its shimmering sequins adorning its shift silhouette – a surefire chic choice for any seasonal celebration. The dress features a crewneck, a tie closure at the back of the neck, and a shift silhouette, snug around the chest and arms while gracefully sitting away from the body through the waist and hips.

Price at the time of publishing: $128

Brand: Kensie | Sizes: 2 to 14 | Colors: Silver, Gold, Black, Fuchsia

Photo: macys.com

Women’s
Dominique Dress

View at Macy’s | $89

The Dominique dress is an exquisite piece featuring a halter design complemented by a handkerchief hemline, adding a playful touch with its strategically placed cutouts. Made with fine pleats and a satin finish, it not only exudes style but also ensures you feel absolutely chic when you slip into it.

Price at the time of publishing: $89

Brand: Petal and Pup | Sizes: 2 to 6 | Colors: Pink, Black

Photo: macys.com

Women’s Logo
Funnel-Neck
Sweatshirt Dress

View at Macy’s | $79.50

This dress embodies a bold and sporty flair, seamlessly fusing the relaxed essence of a sweatshirt with refined elements like a striking funnel neckline, a practical kangaroo pocket, and vibrant signature details that elevate its appeal.

Price at the time of publishing: $79.50

Brand: Tommy Hilfiger | Sizes: XS to XXL | Colors: Scarlet, Sky Captain

Photo: jcpenney.com

Worthington
Short Sleeve Geometric
Fit + Flare Dress

View at JCPenney | $100 $38.99

This Worthington women’s printed fit-and-flare dress is suitable for any occasion. Made from a soft chiffon fabric, this midi dress features short balloon sleeves and a mock neck. Pair it with your favorite heeled sandals, and let the vibrant print speak for itself.

Price at the time of publishing: $100 $38.99

Brand: Worthington | Sizes: XS to XXL | Colors: Aussie Animal, Geo Rotary

Photo: macys.com

Polka-Dot
Midi Dress

View at Macy’s | $99.98 $79.99

Be a little quirky and wear some polka dots. This midi dress is definitely a timeless classic that’s fun and playful. By DKNY and cut to fit and flatter your every curve, this piece is made from stretchy scuba crepe. It also features elegant ruched sleeves and a self-tie belt that accentuates your silhouette.

Price at the time of publication: $99.98 $79.99

Brand: DKNY | Sizes: 2 to 16 | Colors: Midnight/Ivory

Photo: macys.com

Women’s Knitted
Maxi Dress
With Buttons

View at Macy’s | $112 $84

Everyone needs a little black in their wardrobe no matter the season. With its stylish button-front detail and V neckline, this dress combines comfort and flattering fit in a versatile package. It’s ready to accompany you on any occasion.

Price at the time of publishing: $112 $84

Brand: Edikted | Sizes: XS to L | Colors: Black

Photo: macys.com

Women’s
100% Cashmere
Turtleneck
Midi Dress

View at Macy’s | $229 $91.60

Meet this charming cashmere dress by Charter Club, where versatility meets quirky flair. This solid-color dress is the perfect palette for creating a variety of looks. Created for Macy’s, it comes with vents at the hem and a cozy turtleneck. Unlined for that effortless simplicity, it’s easy to slip into with pullover styling.

Price at the time of publishing: $229 $91.60

Brand: Charter Club | Sizes: P/P to XXL | Colors: Heather Camel, Classic Black, Calypso Red, Pink Flame

Photo: macys.com

Mommy and Me
Women’s
Cheetah-Print Dress

View at Macy’s | $99.50 $59.70

Get ready for some fierce and fabulous fashion with your little ladies in this adorable mock-neck dress from I.N.C. International Concepts. It’s trendy and fun, thanks to the bold cat print and puffed sleeves. This flatting A-line look with pullover styling is the purr-fect outfit for your stylish adventures!

Price at the time of publishing: $99.50 $59.70

Brand: I.N.C. International Concepts | Sizes: XS to XXL | Colors: Cheetah

Photo: jcpenney.com

Worthington
Long Sleeve
Shirt Dress

View at JCPenney | $80 $30.98

The brandy brown color of this long-sleeved dress is just trendy for winter. Made from twill, it drapes down your figure and elongates your silhouette, the waist tie adding a delicate touch. With its concealed button-down front and cuffed sleeves, this dress is the ideal partner for a seamless transition from the office hustle to evening drinks.

Price at the time of publishing: $80 $30.98

Brand: | Sizes: XS to XXL | Colors: Brandy Brown, Black

Photo: macys.com

Women’s Striped
Midi Shirtdress

View at Macy’s | $79.50 $47.70

This preppy outfit will definitely get everyone talking – it effortlessly bridges the gap between classic and contemporary. With its crisp front button closures, a flattering self-tie belt cinching the waist, and sassy side slits, this shirtdress is the bomb!

Price at the time of publishing: $79.50 $47.70

Brand: On 34th | Sizes: XXS to XXL | Colors: Fuschia Combo, Cobalt Glaze Blue

Photo: macys.com

Women’s
Elbow-Sleeve
Tiered Maxi Dress

View at Macy’s | $89.50 $53.70

A winter-season dress doesn’t have to be among the palette of light and dark tones. Lined with soft, breathable fabric, this tiered maxi dress features a split neckline with a cinched waist for a flattering fit and elbow-length puff sleeves. This is your new bestie for Casual Fridays to weekend fun. The best part? This baby is made from certified recycled materials.

Price at the time of publishing: $89.50 $53.70

Brand: On 34th | Sizes: XXS to XXL | Colors: Dusted Blue, Dark Forest

Photo: forever21.com

Crepe
Peasant-Sleeve
Maxi Dress

View at Forever21 | $34.99 $27.64

This crepe maxi dress with its V-neckline and long peasant sleeves fits well on any season wardrobe – but it would probably fit better on you. A comfortable fit with its back cutout with self-tie support strap, smocked waist, and column silhouette, it’s flattering on anyone.

Price at the time of publishing: $34.99 $27.64

Brand: Forever21 | Sizes: XS to XL | Colors: Navy, Paul Mauve

Photo: forever21.com

Smocked Chiffon
Peasant-Sleeve Dress

View at Forever21 | $39.99 $39.49

Another black dress to add to your wardrobe. A chiffon midi dress featuring a round neckline, smocked bodice, 3/4 peasant sleeves, ruffle trim, and tiered hem – doesn’t it seem like the perfect dress to wear? But if black isn’t your cup of tea, this cute piece is also available in a nude shade.

Price at the time of publishing: $39.99 $27.99

Brand: Forever21 | Sizes: XS to XXL | Colors: Black, Sandshell, Berry