Ok, let’s be honest. Riding boots have been a thing for a few years now, but it’s not too late to jump on board. The benefit of a trend lasting is that there are many options at all price points, so that benefits the buyer. (Yay!)

A few ground rules about riding boots.

1. They are made to be worn with pants tucked IN THEM, so don’t wear riding boots with a wide leg or boot cut pant. It looks bulky. If you can’t do tucked in, just avoid this trend with pants.

2. If you don’t own skinny jeans, (I suggest you do) you can take a slimmer fit jean and tuck and roll to shove them inside the boot. I think it feels weird, but that’s just me. Here’s a handy pin from Pinterest that shows how to do that.

3. If you wear leggings with your boots remember: LEGGINGS ARE NOT PANTS. What I mean by that- is have a sweater, or tunic, or shirt or SOMETHING that covers your behind. I’m not kidding ladies. It looks non-ladylike (sorry but it does) and honestly, those leggings are not thick enough to wear by themselves. We can see through them. You may not think we can, but TRUST ME… we can.

4. Buy leather. Unless you’re opposed to leather (vegan) I would avoid buying synthetic and get some cute leather boots. They will break in better and look more polished in the long run.

5. Round toe only. Don’t go with a pointy or squared toe. A classic riding boot has a rounded toe, so don’t mess with tradition.

Low Price Range ($0-$100):

Fitzwell Jelly Classic Boot $59.99

Fitzwell Jelly $59.99

Nine West Vintage America Boot $79.99

Nine West Vintage America

Mid Price Range ($100-$200):

Sole Society “Carolyn” $119.99

Sole Society Carolyn Riding Boot $119.95

Enzo Angiolini “Maro: Boot $189.95

Enzo Angiolini Maro Boot $189.95

High Price Range ($200-up):

Frye “Paige” riding boot $377.95

Paige Tall Riding - Cognac $377.95

Tory Burch “Brita” $495

Tory Burch Brita $495

It doesn’t matter if you get black or brown. Just purchase whatever you wear the most of. If all of your shoes now tend to be black, I would obviously stick with black boots.

There are always sales online and in stores, so take the time to find something you love. There’s no rule about buckles or color. Just go with what you love. If you’re a “basics” type of person, don’t go crazy.

Riding boots are awesome, warm, and stylish. The trifecta of fall wardrobe essentials. Grab some and enjoy!


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