5 Seasonal Boots I’m Considering

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.)

7 thoughts on “5 Seasonal Boots I’m Considering

  • Reply Lisa October 22, 2021 at 11:59 am

    Hi Latonya! I bought myself those Nisolo chelsea boots “just to try” (famous last words), and needless to say, they’re here to stay. Feels so good walking in them! Can’t wait for the weather to cooperate a little more. Also, those Aloha boots are 😍

    • Reply latonya October 22, 2021 at 12:23 pm

      Famous last words!!! Those aloha boots have a piece of my heart. So happy you’ve had success!

  • Reply Georgia October 22, 2021 at 5:25 pm

    I have never regretted a purchase from Nisolo! I have their oxfords and Huaraches and if $$ were no object would definitely go for their ankle boots with the chunky heel.

    (Side note- the link to the Christy Dawn victorian style boots takes you to the tall aubergine pair- just mentioning because I’d love to see the style you’re talking about, I own an old pair and I’m debating bringing them out for the season :))

    • Reply latonya October 22, 2021 at 7:32 pm

      Hi Georgia! I love all of you singing Nisolo’s praises. I fixed the link for the Christy Dawn boots, thanks for the heads up!


  • Reply Lauren Andersen October 23, 2021 at 9:40 am

    Those Nisolo’s are my style! I’m going to red to try them!! But I need to know, I also have those tall green hunter boots. I feel like the hunter trend has dying? Or is it not?

    • Reply steph October 23, 2021 at 7:15 pm

      trends never die if youuuu love them 🙂
      i’ve been disappointed w/nisolos. booties i got years ago sit in my closet b/c they are just not comfortable. i recently got the huaraches and while i love the look they’re not very supportive. maybs i just have bad feet? lol.
      my dream boots are a lace up that are similar to the christy dawn but a little little less heel and little more clunk – much better for hikes/my lifestyle. they were ariat riding boots i got secondhand and after wearing them into the ground i just had my beloved zapatero (cobbler) make me a similar pair for an obscenely affordable price. soooo so excited to wear them!

      • Reply latonya October 26, 2021 at 9:47 am

        Lauren! echoing Steph. ALSO. I never noticed it as trend or more as a classic that was ageless.

        Steph, I had a Nisolo pair that I couldn’t wear, so I hear you. I do think for certain feet they just dont work. I thought that I needed to just try a few different styles to get it right?

        omg I love love love when folks find The Right Boot and then are able to hold to it, or even, if ever, make it themselves! I can’t believe it. I have a local cobbler I am practically in love with. The little things matter so much.

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