Top Dress Trends for Fall and Winter 2023, According to a Fashion Stylist

Channel quiet luxury with top dress trends this season.

Cold weather is on the horizon, but that doesn't mean your dresses can only be worn in the summer. The transition from summer to fall and winter can be challenging, but there's so many different ways to style dresses. Upgrade your wardrobe with these stylish dress must-haves for this season. We talked to fashion stylist Candice Lambert McAndrews on how to style seasonal dress favorites.

“This fall, it's been kind of elevated. [I feel like] sophisticated sweater dresses [and] classic styles are back. Kind of a quiet luxury vibe,” explains McAndrews. The classic sweater dresses are on trend for this fall and winter. “I've seen them all over, there's some really cool different ones,” says McAndrews. She recommends checking out Simkhai for edgier styles, Anthropologie for bright color cables, and ASOS for various styles at a good price point.

Daytime Dress Styles

McAndrews reaches for casual dresses for a daytime look. “I like to always keep it clean. In that sense, like easy and accessible,” says McAndrews. Pair a casual dress with a sneaker, loafer, or a combat boot that are ideal for daytime. There’s freedom in the daytime to get edgy with accessories. McAndrews seeks statement pieces such as a statement gold necklace or gold hoop during the day.

Nighttime Dress Styles

Channeling her inner 'Sex and the City' girl with a Cosmopolitan in hand, McAndrews says she “[would] probably pick something that is a little more flirty and fun. Maybe a pattern, color, or something to make it just pop and be a little more special,” explains McAndrews.

Nighttime is all about layering your outfit to make it more elevated. “I would definitely do like a blazer or a jacket, maybe overdressed with a heel. The accessories may be a little bit more fun. Maybe the hoop is a diamond hoop or some kind of fun dangly earring, bracelets, and maybe a color pump,” says McAndrews.

Would you Rather: Dress Edition

We asked McAndrews a series of would you rather questions to uncover her top dress picks. 

Mini Dress or Maxi Dress?

"The last few years have been all about skin. For me I think that's hot and sexy, but I'm really about structure and architecture in fashion and really presenting an idea with your clothes and expression. Wearing sheer and showing skin is an expression as well, but I feel like I've seen that so much that I really just want to see people come out and explore wearing things,” says McAndrews. The maxi dress is an effortless way to look put-together and stay warm this fall and winter.

Jumpsuit or Romper?

A romper style is versatile and perfect for every occasion. “I like a romper that has a little bit of a cargo vibe to it and a little bit of a drop crotch…I love ones that have a low back and a high neck or maybe a bell pant,” explains McAndrews. She recommends ALC for great rompers that can work for both daytime and evening wear.

Floral Dress or Black Dress?

The toughest would you rather question-the battle between femininity and neutral hues. “Depends on the day, right? I love to wear black because it's easy to accessorize, but I do have this side of me that loves a floral just because it can be worn [in] so many ways,” explains McAndrews. Layering is the key to wearing a floral dress in fall and winter. “I'd love to do a floral in the winter with a long cardigan or a double breasted winter coat and beanie,” says McAndrews. She also recommends pairing a floral dress with tights or leggings, and a boot.

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