One of you lovely readers requested a fall boot guide and of course now I can’t find your comment or direct message to remember your name! Please let me know if it was you. 🙂 I decided to split this into separate categories for ankle boots (booties), riding boots, and over-the-knee boots as all three are fall must-haves for me. Happy shopping!

fall boot guide design darling ankle boots

one  //  two  //  three  //  four  //  five  //  six  //  seven  //  eight

I picked up this pair of suede ankle boots before our honeymoon and proceeded to live in them the entire trip. The shape is similar to this pair that I wore into the ground last fall and winter, which I still recommend as a great affordable alternative. I’m 5’1″ and pretty used to wearing heels so I don’t mind the height on either style, but I included some lower heel options like these, thesethese that offer a similar look that’s more practical for everyday wear.

fall boot guide design darling riding boots

one  //  two  //  three  //  four  //  five  //  six

I fell in love with these J.Crew riding boots but sadly they were too tall for me and kept scrunching up over my knees. But if you’re taller than I am, I seriously think they’re the perfect classic riding boot! And if money is no object, these are basically the riding boots of my dreams. But this pair is a similar style under $200! I have a pair of suede Tory Burch riding boots that I love and this leather style is a chic update. And lastly, our friend Paul’s business Tecovas just came out with a western-inspired equestrian boot that I’m obsessed with.

fall boot guide design darling over the knee boots

one  //  two  //  three  //  four  //  five  //  six  //  seven  //  eight

I’ve had this pair of navy suede over-the-knee boots from Stuart Weitzman for four or five years and they’re still in great shape thanks to a recent trip to the cobbler. I know the price tag can be a tough pill to swallow but I’ve gotten so much wear out of mine that I’m seriously considering getting a brown pair by the same designer. I have a tan suede pair that J.Crew made last year which I also love and thankfully Madewell has a pretty similar pair out this season (albeit with a slightly higher heel). But if it’s your first foray into over-the-knee boots and you’re not looking to make a big investment, you’d never know this pair or this pair were under $200.

Shop the post:

8 thoughts on “FALL BOOT GUIDE

Leave a Reply

Your email address will not be published.

  1. I was the one who requested the post and I love your selections of boots! I get so overwhelmed when I go looking for boots myself so this is amazing. Thank you!

  2. Curious about your color choice – you only show one pair of black boots. The others are within a relatively narrow range of brown. Is that because black boots are out and brown are in?

    1. Haha thanks for pointing this out — just my preferred / most worn boot color! Black will forever be “in” but I wear very little of it so all these are brown/tan plus one navy pair. Most of them are available in multiple colors; I should have mentioned that in my post!

  3. I was not the reader that requested this post – but I am so glad someone did! I have been wanted a pair of boots for the fall and am so happy you made this post. I’m appreciative of the variety along with the affordable options. Also, thank you times a million for including affordable over the knee boots haha! I have been dreaming of some but most people tend to only talk about the SW ones! Love this post.