STYLE

8 Maxi Dresses You Need This Season

December 23, 2025

Cooler days call for longer hemlines and smart layers. Discover our picks for the best maxi dresses from Cynthia Cook Smith.

Meet Our Expert:
Cynthia Cook Smith

During her time at Vogue, Cynthia worked behind the scenes at everything from fashion shows to the Met Gala, helping dress people for major events. Nearly ten years later, she now styles clients for both special occasions and everyday life.

Learn more about cynthia

What Is a Maxi Dress?

Long and effortless, a maxi dress is a staple in any wardrobe. We define a maxi as any dress beyond 49 inches long—which is well below the knee on most. Easy to wear from day to night, this duster-length style goes almost anywhere everywhere and pairs with just about everything.

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How Do You Style a Dress
in Colder Weather?

As we transition from fall into winter, it can feel like there are less opportunities to be stylish. But, to us, the more layers, the better. That’s why we’re loving longer maxi dresses with long coats, big boots, and cozy sweaters. Channeling ’90s style and seasonal neutrals, here are eight
looks to copy.

1. Cream Henley

A ribbed-knit cream sweater dress looks like something Gwyneth Paltrow would wear in A Perfect Murder—plus, the long length makes it ageless and great for fall and winter dressing. Keep things effortless with a navy wool coat and chocolate brown boots. Neutral colors almost always look better together.

Callum Dress

Suede Mira Boots

Wool Trinity Coat

Kaia Bag

2. Cashmere Casual

This time of year calls for cashmere. The answer? This stylish, yet understated cashmere dress. Elevate your everyday with timeless touches like a micro belt,
pointed-toe boots, and a maroon bag.

Cashmere Turtleneck Maxi Dress

Oval Buckle Skinny Belt

Vinnie 85 Zip Booties

Suede Moon Hobo

3. Warm Neutral

A warm, earthy palette of rich browns does wonders in colder weather. Play with organic shapes and textures with a suede tote with some dimension to it. A tight collar or statement necklace finishes the look.

Dora Maxi Dress

Suede Mira Boots

Suede Dimple Tote

Torque Statement Necklace

4. Printed Statement

La DoubleJ makes some of the most unique, colorful prints on the market. Follow the muted sage and rust tones of the dress through your accessories: a great mule and a suede bag.

Placee Long Sleeve Swing Dress

Austen Mule

Suede Mini Boomerang Bag

Michelle Earrings

5. Polka Dot Dressy

Polka dots are everywhere right now. Made in a dotted jacquard, this Saylor dress is playful and fun to pair with rich materials like leather and suede. Cynthia loves the combination of a leather jacket with a buck (or brown) suede boot.

Narah Maxi Dress

Raffeala Up Mid Boots

Reversible Brella Jacket

Gold Infinity Huggie Earrings

6. Green Beauty

This under-$200 dress is the easy, throw-on-and-go dress made for the holidays. Add an extra touch of sparkle with the shimmer knit and pair it with stylish, yet understated, accessories.

Knit Cammie Maxi Dress

Mimi Heels

Trumbull Earrings

Haven Woven Clutch

7. Taffeta Threads

Have an invite somewhere special? Go with a dress in a rich, luxe fabric that photographs well. Pro tip: a LBD with shining accessories is a timeless look you can wear more than just once.

Simmons Column Dress

Sophia Heels

Ela Crystal Mesh Clutch

Camille Earrings

8. Gala Glam

A jacquard dress always makes a bold statement, but especially in the cold weather months. Wear this incredible dress with pared-back accessories that really allow for it to shine.