Here's Exactly How to Wear a Summer Dress in Fall

Fall is around the corner, and I always feel equal parts excited and sad to transition my wardrobe. The colors, textures, and layers of autumn are my favorite to dress for, but it’s hard to say goodbye to warm-weather pieces, especially my summer dresses.

Thankfully, there’s always a period of weeks where warm afternoons are bookended by cool mornings and evenings, making layering an essential part of getting ready. And when you’re slipping on and off cardigans, sweaters, and jackets throughout the day, a summer dress makes the perfect base.

With that in mind, don’t put away your summer dresses just yet! With the right styling, layering, and seasonal accessories, you can wear this past season’s maxis, minis, and sundresses well into cooler weather.

See below for styling tips to layer and accessorize a summer dress for fall, plus a few outfit ideas for everything from weekend to the office.

How Wear Summer Dresses in Fall: 7 Outfit Ideas

1. Sleeveless Midi Dress + Sweater Over the Shoulders + Closed-Toe Shoe

It’s hard to part ways with the ease of a cotton summer dress. Keep your favorites around for early fall by draping a lightweight sweater over the shoulders and adding closed-toe shoes, like sneakers, ballet flats, or mules.

2. Knit or Crochet Dress + Cropped Jacket + Booties

A crochet or knit dress is perfect for transitional weeks when it’s warm during the day. Just add a denim, utility, moto, or leather jacket. You can wear this look with sandals early on, with flats as the weather chills, and with ankle boots and tights in the colder months.

3. Floral Sundress + Dark Belt + Dark Boots

A floral print sundress feels floaty and summery, but you can incorporate a moody fall vibe with dark accessories. A black belt and black knee high boots could take a summer dress like this all the way into the holiday season.

4. Long-Sleeve Summer Mini + Boots

This is possibly the easiest way to transition summer dresses to fall (and my personal favorite!). Everything from knee-high to mid-calf and traditional ankle booties works. If your dress is short sleeved or sleeveless, a moto jacket or blazer will pull the look together and keep you warm on cool evenings.

5. Cropped Sweater + Midi or Maxi Dress

Once it’s properly chilly, try throwing a cropped sweater over your favorite summer midi or maxi. Cropped sweaters and cardigans that have voluminous sleeves like this will help maintain shape at the waist and add balance at the shoulders. If you don’t have a cropped sweater in your fall wardrobe, you can get the waist definition using the belt sweater tuck technique in this post.

6. Long Summer Dress + Equal Length Outerwear

This one’s often overlooked because it can be hard to nail. It works best with long summer dresses and outerwear that’s equally as long or just slightly shorter. An example would be a white summer maxi dress and a long trench coat finished with heeled ankle booties.

7. Slip Dress + Oversized Sweater

Take the ease of throwing on a simple slip dress into fall by treating it like a slip skirt and wearing an oversized or chunky sweater on top. You may need to finesse the styling, depending on the sweater you choose, and decide on a case by case basis whether a front tuck, full tuck, or no tuck is needed. Early in the fall you could try this with sandals, but for the chilly months, suede or leather pumps will keep your toes warm.

I hope these summer dress in fall outfit ideas help you extend those warm weather favorites just a few weeks or months into the cooler seasons. If you have any questions about transitioning a warm weather dress to create a fall look feel free to drop them in the comments!