At the time of my writing this post, it is currently pushing 80 degrees in November, so it feels quite timely to share this post considering I am constantly trying to think seasonally appropriate while also temperature appropriate. Sweater dresses are the way to go! They are easy to style, are often cozy and comfortable, and can be dressed up or down. So, today, I am sharing a roundup of ways to style a sweater dress for various occasions this fall and winter.

Sweater Dress Outfits

I have acquired quite a collection of sweater dresses throughout the years and am constantly looking for inspiration on how to style them on Instagram or Pinterest! I find them to be appropriate for many social situations and even for working from home to stay comfy while still feeling put together. Sweater dresses are a great alternative to jeans during the cooler seasons. They are also a great option for when it is unseasonably warm outside, yet you still want to be dressed for the season. Here are several outfit ideas.

How to Style a Sweater Dress

Turtleneck Sweater Dress with Knee High Boots

I picked this sweater dress up last year before heading to Chicago to stay at Le Méridien Essex and it quickly fell into the rotation. There is a fair isle version this year that is equally lovely! And how great are these boots?

Off-the-Shoulder Dress with Booties

Photos by GloryRoze Photography

This sweater dress is one of my favorite sweater dresses to wear for a night out in the fall and winter on warmer nights. The fabric is pretty light and breathable. I picked up these booties (old, similar linked) several years ago and I consistently reach for them, especially to pair with this dress. Seen here on a date night in Durham & for dinner in Wilmington on a coastal holiday weekend getaway

Turtleneck Sweater with Ballon Sleeves paired with Ankle Booties

This sweater dress is a J.Crew oldie but a goodie for me in my fall/winter closet. They currently do not have anything similar on their site, but this one from H&M has similar balloon sleeves and a similar neck style on this one. I had the flat booties pictured for years and wore them until they finally fell apart. Here is a pair that is pretty similar.

Cowl Neck Sweater Dress with Over-the-Knee Boots

This outfit is probably one of my favorites when it comes to wearing a sweater dress. David and I took a trip to New Orleans and stayed at the La Pavillon between Christmas and New Year’s Eve and the weather was delightful. This shorter sweater dress (with pockets!) was paired with thigh-high boots.

Layer a Sweater Over a Dress

While I may be bending the rules here a bit, I love layering a sweater over a dress to get more wear out of dresses. I recently added this sweater to my collection to do just that. I pair this when it is still really warm with open-toe shoes as seen above or with my favorite knee high boots.

Sweater Dress Over Leggings

If you are on the taller side like me (I’m 5’8″ for reference), you may find that traditional sweater dresses are too short to wear without something underneath. I generally like to pair longer sweaters like this one with my Spanx faux leather leggings and booties of some sort. If we are traveling, I generally reach for my combat boots and if it is really cold, I’ll pair with my J.Crew Nordic boots.

Sweater Dress Layered with a Coat & Mules

Photo via Louise Roe

I love this color combo with this dress (similar here) with a cognac overcoat and mules. It is one of those looks that can be dressed up or down.

Sweater Dress Paired with a Faux Leather Jacket

Photo via Allyson in Wonderland

I love this black sweater dress paired with a leather (or faux leather) jacket. Also, how fun are those sunnies! This midi sweater dress is a beautiful option, too!

Sweater Dress Paired with Combat Boots

Photo via Style Report

I love a classic black dress paired with combat boots!

Sweater Dress Paired with Sneakers

Photo via Pinterest

I love this outfit for a casual weekend outing or cheering on your favorite sports team. Here is a long-sleeved sweater dress and a great pair of classic white sneakers. I also love this Yankees hat and I wear it all the time. I would love to add this one to my hat collection as well.