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Home Entertainment

These 17 Rich-Looking Fall Boots Pair Perfectly with Dresses

by DigestWire member
August 30, 2025
in Entertainment
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These 17 Rich-Looking Fall Boots Pair Perfectly with Dresses
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Boots and dresses are one fall fashion combo that’s never going out of style. As we prepare our fall wardrobes, we’re making it a priority to ensure our footwear is in tip-top shape.

The good news? Boots don’t have to cost a fortune to be stylish. In fact, the majority of our favorite boots that pair well with dresses are under $60. Here are our favorite Amazon-found pairs that’ll have you ready for leaf stomping and pumpkin picking.

17 Rich-Looking Boots That Pair Well With Dresses

1. Our Favorite: These Dream Pairs boots are a classic that you can throw on day after day. The hardest part is picking a color!

2. Simple Belt: For something with a bit more shine, these low-heel riding boots have a buckle on either ankle for extra pizazz.

3. All One Color: Go for a sleek, leg-slimming look with these 2-inch heeled boots that go nearly to the knee.

4. Suede Beauties: Tall suede boots automatically look fall-ready, but this fairly priced pair also comes in a leather-like material if you want to switch it up.

5. Cowboy Carter: These pointed-toe cowboy boots don’t look overly western, so you can rock them on the daily.

6. Night Out-Ready: You’ll give total rich-mom vibes in these to-the-knee boots with a chunky, 3.35-inch heel.

7. Short and Sweet: There’s something about tall boots that look super sleek with dresses, but mid-calf boots are just as classic.

8. Sexy and Slouchy: Suede-like material and a relaxed fit make these Amazon Essentials boots a total win.

9. Ankle Boots: At under $40, these sleek ankle boots are a versatile fall staple you’ll wear with dresses, skirts and jeans alike.

10. Chunky Heel: Get the height without walking like a newborn giraffe, thanks to these leather platform boots that’ll have you walking steady.

11. Winter White: Don’t pack away your white dresses just yet! They’ll look super chic when paired with these to-the-knee white boots that can be worn well through winter.

12. Splurge-Worthy: Treat yourself to real leather boots from Madewell that actually stand the test of time.

13. Instant Wow Factor: Over-the-knee boots are a guaranteed way to make whatever you’re wearing look a whole lot more sexy. Bonus: This pick is under $55!

14. Fold-Over Find: Yes, you can totally pull off tall fold-over boots, especially if you pair them with a shorter dress so that they get the spotlight they deserve.

15. Mid-Calf Cowgirl: For under $50, it’s worth trying these embroidered cowboy boots that spice up simple dresses.

16. Stretchy Style: Although these knee-high boots are fitted, they’re stretchy enough to fit different calf sizes. Plus, the burgundy color practically screams ‘rich girl fall.’

17. Plain Jane: It’s surprisingly difficult to find a simple riding boot without extra hardware details, but this no-frills option goes with any dress.

17 Comfy, Late-Summer Dresses Under $40 on Amazon

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