With summer coming to a close, we're gearing up to enter my favorite season: fall. More specifically, it's almost dress-and-boots season. As the temperatures slowly start to drop, it's the ideal time to marry the best parts of summer and fall to create a chic, effortless outfit. The classic combination of a dress with boots balances the transitional season and makes outfit planning that much easier. Not only does it help extend the life of your favorite dresses, but it also allows you to break out your fall boots before the weather actually warrants it.
Whether you go mini, midi, or maxi, there's a boot style out there for your favorite summer dress. From sleek knee-high silhouettes to Western styles to moto-inspired ankle boots, pairing one of these with a summer dress helps carry them over into the new season. Boots happen to be a weakness of mine, so I've spent the past few weeks getting a head start on shopping. I've scoured the internet for the best fall boots to wear with dresses, which I'm highlighting below. Keep scrolling for the 31 pairs I'm eyeing.
This color is so unique.
Equal parts Western and modern.
These look infinitely more expensive than they are.
These perfectly complement a midi dress.
Add a little edge to your outfit.
Truly timeless.
Moto boots are making a comeback this season.
These look so chic with a minidress.
The toe makes these stand out.
Zara's shoe selection is really good right now.
The perfect partner for miniskirts.
Now here are boots you'll wear for years.
My jaw dropped.
The name is almost as good as the boots.
Wear with dresses now and jeans through winter.
Nothing says fall like brown suede.
I love the color combo on these.
The internet is losing it over these.
Found my new night-out boots.
These have been on my wish list for years now.
Same with the tall version.
Everyone needs a good pair of knee-high black boots.
The fit of these is *chef's kiss.*
The ideal height for a maxi dress.
These are stunning.
Western boots are still going strong, and these are quite elevated.
The ideal heel height.
These look equally chic with dresses and jeans.
Nobody does luxe Western better than Isabel Marant.
Okay, Mango.
The two-tone colorway is a unique take on the Western trend.
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Olivia Rodrigo Just Found the Next It Shoes to Wear With DressesThey're fresher than Western boots.
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J.Lo Wore the Classic Two-Item Outfit That Looks Elegant Every Single TimeThe Birkin helps.
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The Nordstrom Spring Sale Has So Many Chic Shoes—I'm Losing It Over These FindsGood luck picking just one.
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I'm Saving This '90s Supermodel's Airport Looks for All My Travel Days in 2024Each one is comfortable and super chic.
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The Anti–It Bags Fashion People Are Just Really IntoThey have major staying power.
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I'm Making Some Designer Investments This Year—30 Items I'm Eyeing From MyTheresaNo gatekeeping here.
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Gisele Bündchen Wore a Trench Coat With Nothing But Knee-High Boots During NYFWNo one does it like her.
