In prepping this post I realized how few dresses I have been wearing lately. However, in creating these styles, I also noticed how great and easy fall dresses are to wear. They are simple and chic and look great when dressed up or worn more casually. You can wear the same dress so many ways based on the shoes you choose and how you accessorize. Your shoes give your outfit a whole different vibe based on what styles you wear, which I am demonstrating in this post. Keep reading for styles of fall shoes to wear with dresses.
Related: What Shoes to Wear with Leather Pants
10 Fall Shoes To Wear With Dresses
Booties
Possibly my favorite fall footwear is booties. I have tons and love styling them with different outfits. The below styles are great showing so many different dresses you can wear with booties. A knit t-shirt dress is great for a casual style paired with booties. A shirtdress is great for a more professional look with booties to wear to the office. Finally, a ruched cocktail dress is perfect to pair with booties for a gathering or evening out.
Pumps or Closed-Toe Heels
Pumps are naturally a more dressy style of shoe. You can wear them professionally or to an event, but pumps will be a good go-to for a more formal affair. I wore the burgundy dress and heels to a wedding and it was a great fall outfit to celebrate the couple. On the right, You can see I have a shirtdress paired with a blazer and pumps for a business professional look. This is something I would wear to a presentation or important business meeting.
Ballet Flats
Ballet flats are always around but have made a massive resurgance lately. The below photos are older, and I intended to update them, but as I had my perforated mary jane flats out ready for photos, my dog ate them. Yes, my dog ate my homework! So for now, until I get a new pair, the below styles are still up to date and show how you can wear flats more casually with a knit dress and denim jacket, or with a blouse and suede style for a more dressed up look.
Knee High Boots
I love a classic knee high boot as fall shoes to wear with dresses, and these brown crocodile ones were top of my shopping list last year. I haven’t worn them nearly enough so I try to break them out as much as possible. LAtely I’ve been wearing them with skirts, but this was a great opportunity to style them with a sweater dress for winter. This look is definitely more upscale, but I think it could be worn to an office with a conservative dress. Otherwise I’d wear them to dinner, dates, or girls’ nights.
Slouchy Suede Boots
My slouchy suede boots are really old but they’ve gotten so much use over the years. They are so cute and classic, and a more casual boot option as opposed to the previous pointed toe stiletto style. Both of these looks below are shirt dresses with sweaters, I think they give off totally different vibes. While both are perfectly acceptable for an office environment, the plaid is a bit more casual and the white is a crisper, more professional look.
Sneakers
Sneakers are such a great way to dress down any fall dress. While I wouldn’t choose a cocktail dress with sneakers, this shirt dress or any knit dress would be an excellent choice. Of course sneakers are cool and teens live in them these days, but I just love them for comfort. Dresses can be, at times less comfortable than pants for me, so sneakers are a great way to balance the comfort level.
Loafers
This look below would be my first choice for a visit to the office in early fall. I would add a jacket as the weather got cooler. The shirtdress style is perfect paired with the chunky loafers. It’s a great fall outfit and perfect for a semi-casual occasion where you still want to look professional or put together, and still be comfortable.
Heeled Sandals
Cocktail dresses need heels! I think, while open toe, heel sandals are still some of the best fall shoes to wear with dresses. I love a heel sandal with a pretty dress. The outfit below is perfect for a night out, event, or wedding, I actually wore this exact outfit to an early fall wedding! I love the fun pop of color with the black dress but you can mix and match colors and styles however works for you!
Ankle Boots
While we already covered booties, I had to separate out these ankle boots. They are such a different style and I wear them in different instances. While you could absolutely choose booties for this look, these ankle boots come up farther on the leg, and provide a great classy and slightly more upscale look.
Mules
Once we get into rainy or wet season in Texas we are out on the mules and open shoes, so I always have to break them out in early fall. These pink mules are such a fun and cure style with this fall dress, allowing to show off your leg. Especially in Texas, with the rapidly changing weather, you can wear these from morning to night and not worry that you’ll be melting in a leather boot by lunch.
How To Match Shoes With Dresses
Start with the Occasion
Matching shoes with dresses is the same process as choosing shoes to wear with any outfit. First think of your occasion. For a cocktail party or wedding you would choose a fancier shoe, so likely not loafers or sneakers. On the opposite side, if you’re running errands and want to be casual you’ll leave the boots at home and opt for a ballet flat or sneaker.
Choose the shoe that best matches your occasion, i.e. leaders or pumps for the office, heeled sandals for a wedding, ballet flats for brunch, and sneakers for errands.
Think About the Weather
Unfortunately weather ruins many-a well-planned outfit. You won’t want to wear suede loafers or mules in the rain, so you may opt for a more sturdy sneaker or bootie. The heat also kills tons of boots outfits for me in Texas. It starts out chilly but ends up getting hot so knee high boots are reserved for only the coolest nights.
Don’t Forget Comfort
I am finally at the age where I prioritize comfort over style in *some* cases. You won’t find me in orthopedics any time soon, but if I am on my feet for a long time I will opt for a chunkier heel, or ballet flat. Especially at work I choose booties and loafers more than heels. Comfort is important! Even at a wedding, I still wear heels, but I choose ones that I KNOW I can handle all night long. Don’t be that girl who takes their shoes off. It’s gross and unsanitary. Bring something to change into if you can’t handle your heels, that is always a great option!
Color Match or Compliment
Of course, the color of the shoe makes a huge impact. If you want a fun pop of color choose a bright option. Monochrome looks are completed by the shoes, so always keep that in mind if you’re going for a singular-color style. Finally don’t be afraid of mixing neutrals. Brown can go with black, just make sure it flows throughout your outfit, like a brown bag or a belt with brown shoes.
Follow me on Instagram!