What’s your ideal autumnal boot? Of course, I say autumnal, because the use of a boot varies largely between fall and winter. In the winter, I’m looking for pretty much anything to keep me warm, that’s remotely appealing, and also stable enough for slippery city sidewalks. The fall promises more outfit options. And while the weather these days often seems wild (ranging from 60 to 77 within a few days), my desire for that semi perfect seasonal boot is palpable. 

The other day my friend Karyn posted an instagram story asking myself and four of her friends about the boots she just purchased. “Do I keep these?!” she questioned while trying on a handful of different outfits. Karyn is a stylist and single-handedly the most stylish person I know. Her question made me giggle, because the seasonal cute boot dilemma affects us all!

I was no help to Karyn, really. I said the boots only worked with a mini short set or a mini skirt. “Yes!” Karyn quipped. And that was that. But my own search for the perfect fall boot (while we are well in it) still stands.

In the meantime, here are five I’m eyeing (and keeping in my cart) if you’re interested:

+ I’m obsessed with the tonal feel of these Timberland Chelsea boots

+ I very rarely dream of a boot. But these off-white Alohas riding boots have been popping up in my dreams!

+ I think the Nisolo Chelsea boots are the ideal chunky sweater every day pair

+ Okay, let’s just say if we had all the money in the world. WOAH. These stretch Aubergine boots are it!

+ In 2010 and 2011 I had a vintage pair of boots that look similarly to this Victorian style pair form Christy Dawn. I’m not sure if I could pull of the narrow style now, but it’s nice to get nostalgic about it all.

Any that interest you?

(Photography by Kelsey Cherry for LY. This post includes affiliate links. If you choose to purchase something, we may earn a small commission. As always, thank you for supporting our small business.)