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, it’s the perfect time to 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, as well as some of my tried and true favorites.
11 FALL SHOES TO WEAR WITH DRESSES
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 also love these pointed toe flats with an ankle strap if you find your feet are constantly slipping.
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 satin version). These pair great with any type of dress, from mini dresses to maxi!
These Sam Edelman leather mules are a fantastic shoe option! They’re comfortable, stylish, and a great early-fall shoe to pair with a dress before the weather get’s too cold. Also love the white and brown versions. If you really want to splurge, my beloved Gucci loafers are an investment but so worth it IMO!
I love the look of a sporty dress with a sneaker and jacket for the fall. There are so many fun white sneakers out right now! This option with velcro straps is so cute, I also love these sneakers with a touch of metallic. If you’ve been following for a while, you know I also adore my Converse high tops!
5. Ankle Boots
One of my favorites shoes to wear! These ankle boots are a fall and winter staple for me and they look so cute with dresses. I also love the brown version of these Staud boots. These leather ankle boots from Everlane are also a great choice and come in a few different colors.
Chelsea boots were big last fall and I’m excited to see them trending again this year. They’re a great shoe option for rainier, colder days and super comfy.
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! This lug sole version is very on trend.
Channel your inner Blair Waldorf and pair loafers with your dresses this fall! I’m loving the loafer trend, I suggest pairing with these darling swiss-dot socks to help avoid blisters!
9. Combat Boots
Another on-trend shoe for the season! Add a hint of 90s grunge to your outfit with a pair of lace up combat boots. Great for when you’re doing more walking, when it’s chillier, or when you have a more formal dress you want to make more casual.
10. Knee High Boots
Heads up girls, trade in your over the knee boots for knee high boots this fall! I think this is a bit more of a classic silhouette and I’m happy to make the swap. I think this black leather pair is also great, and these are so chic if you like a heel and would look so sleek with a midi dress.
11. Block Heels
I adore a fabulous pair of high heels, especially in luxurious velvet for fall. For an open toe moment, these block heel mules are great for a special occasion (I am obsessed with the gold version, one of my all time favorite pairs of shoes.) I think these heels are also so chic and polished. I’ve found these block heel sandals also last me into early fall. And these Sam Edelman block heels are a workhorse!
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!
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!)
Not technically a dress, but you get the idea! I adore this monochromatic navy look (J.Crew slip skirt and classic cashmere sweater) paired with my leather Gucci loafers. Who says you can’t mix black and navy!?
I’m obsessed with the look of this Staud midi sweater dress paired with block heels. The colorblocking is just so flattering. Sadly I can’t track down this exact color way, but I’m loving this green version, this brown and white version, and this version with black edging. Might need to add a new color to my wardrobe this fall! Paired with these classic Sam Edelman block heels but would also be great with ankle boots.