11 Fall Shoes To Wear With Dresses

I don’t know about you, but I’ve definitely caught the fall bug! Bring on the crunchy leaves, perfectly cool days, new fall clothes and queue up the You’ve Got Mail rewatch. As the temperature starts to cool down (thankfully!), it’s the perfect time to break out transitional wardrobe pieces and experiment with different looks, textures, types of shoes, and outfit combinations.

I think switching out shoe options is a great way to transform an outfit, and of course keep you warm while staying stylish throughout the season! Today I’m sharing a roundup of fall shoes that pair well with dresses (including fall wedding guest dresses!), as well as some of my tried and true favorites.

11 FALL SHOES TO WEAR WITH DRESSES

1. Pointed Toe Flats

A classic fall shoe! Pointed toe flats are a great way to elongate your leg or dress up a more casual outfit. I think it’s useful to have both a brown and black pair in your closet for versatility. I think this slingback pair is super versatile as well.

2. Ballet Flats

Ballet flats are back in a big way this season! Anyone else have minor PTSD from the early ’00s ballet flat era? If you can get past it, there are lots of fun new takes on the style (like a woven version or velvet pair). These pair great with any type of dress, from mini dresses to maxi!

3. Leather Mules

These Sam Edelman leather mules are a fantastic shoe option under $150! They’re comfortable, stylish, and a great early-fall shoe to pair with a dress before the weather get’s too cold. If you really want to splurge, my beloved Gucci mules are an investment but so worth it IMO! This is a similar looking pair for way less.

4. Sneakers

I love the look of a sporty dress with a sneaker and jacket for the fall. There are so many fun sneakers out right now! I’ve been loving my white and green Adidas Sambas, but there are so many other interesting color combos. These sneakers with velcro straps are so cute, I also love the look of these suede sneakers under $150. If you’ve been following for a while, you know I also adore my Converse high tops!

5. Ankle Boots

It’s finally boot season! Ankle boots are a fall and winter staple for me and they look so cute with dresses. This year is all about the kitten heel ankle boot. This pair comes in a handful of colors, and this kitten heel pair is so chic!

6. Chelsea Boots

Chelsea boots were big last fall and I’m excited to see them trending again this year. They’re a great shoe option for rainy, cold days when you need something that can handle the weather but are still comfy. I suggest opting for a waterproof or at least water resistant pair.

7. Mary Janes

Another fun flat option to wear with dresses this fall! I’m loving the chic flair they add to any outfit. A great option if you work in a corporate or formal environment! These have a more square toe, and these are an investment but well worth it!

8. Loafers

Channel your inner Blair Waldorf and pair loafers with your dresses this fall! I’m loving the loafer trend, I suggest pairing with chic sheer socks too help avoid blisters! These Gucci loafers a wardrobe investment, but so versatile.

9. Slingback Heels

A chic pair of slingback heels pairs perfectly with wide leg trousers, denim, dresses, or skirts. This cap toe version is so classic, also love this pair (perfect to wear with skirts or dresses to the office).

10. Knee High Boots

Heads up girls, trade in your over the knee boots for knee high boots this fall! I’m loving the western inspired feel of the ones I linked above, and these are so chic if you like a heel and would look so sleek with a midi dress. For a lower heel, opt for these!

11. Platform Heels

I adore a fabulous pair of high heels, especially in luxurious velvet for fall. This pair under $200 are perfect for the holiday season, and these are super versatile for fall and winter.

Fall Dress Outfits

Here are a roundup of some fall dress outfits of years past, I’m so excited to recreate some of these in the upcoming months! It’s fun to mix classic pieces I’ve had for years with more trendy items, and also see items that come back into style!

Fall Dress Outfit

This is one of my favorite early fall dresses, the color and shape feel like autumn but it’s still lightweight enough to wear in warmer temps. This dress is sold out, but here is a similar smocked dress. Pair with my favorite block heel sandals (maybe one of my most worn shoes this year!)

monochromatic navy look

Not technically a dress, but you get the idea! I adore this monochromatic navy look paired with my leather Gucci loafers. Who says you can’t mix black and navy!?

Staud midi sweater dress

I’m obsessed with the look of this Staud midi sweater dress paired with block heels. The colorblocking is just so flattering! Also love this color, and this color. Might need to add a new color to my wardrobe this fall! Paired with these classic Sam Edelman block heels.

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