The IWTBH Fall Shoe Guide: Sexy Knee-High Boots

I have had heeled, dress-and-skirt friendly boots on the brain as soon as the first wave of crisp air hit New York. And I also love them over skinny jeans or under wider boyfriend-y ones rolled up. First up: This cool slouchy embossed vegan pair that instantly elevates the frayed denim skirt
Here’s a chic understated A.P.C.esque one for under $200. 
These feel very ’70s and would be perfect with floaty feminine dresses.
Here’s a cool snake-embossed style that would make any plain black jeans or a simple skirt way more fun.
Loeffler Randall’s streamlined black number would be perfect with fall classics like tweed jackets and shirt dresses.
You can’t so wrong with camel suede, and this Splendid boot is an easy everyday shape to wear with all kinds of blue and black denim.
This pair has a slight Mary Tyler Moore shape and is kind of calling out for a camel A-line skirt!
These Vince Camutos have a cool patchwork detail, and are very much on the Ulla Johnson tip.
The square toe and cubed heel here are giving off some real Françoise Hardy- Anne-France Dautheville vibes. 
This chic pair is by none other than Naturalizer, so you know they’re comfy!

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  1. Love a lot of these, but as someone with some muscle tone in her calves, I’ve basically given up on anything higher than an ankle boot. 2 pairs of these boots have 15″ calf circumference – all others are 14.75″ or smaller, and none offered a wide calf option (that I could find).

    It’s such a bummer that this isn’t something considered by a wider range of footwear designers, as it seems to be a relatively common problem. Erica Davies (@erica_davies, British fashion editor) had a fascinating conversation about this on Instagram yesterday (expanded within her Stories).

    The fashion industry finally seems to be a bit more focused on size-inclusivity, and hopefully that will make its way to boots soon too!

    (Of course this isn’t a commentary on Andrea or her wonderful work, but the broader clothing manufacturers at large!)

    1. As a lady with muscular calves I’ve found some success with Madewell tall boots that usually offer a wide calf width. I’ve also had good experience with Frye boots 🙂

    2. For anyone with calves outside the average range (plus or minus), please check out Duo Boots from the UK. I have bought multiple pairs from there. They have custom calf sizes going from 30-50cm (about 12-20 inches), and you tailor the calf size and the shoe size. As someone who could NEVER find knee-high boots that fit me, this place is amazing. The shipping from the UK is quick, the customer service is amazing (you can call them up and chat to them about things like what styles are best for wide/narrow ankles, wide/narrow feet, etc.). The quality has been great–I have leather, suede, and all have lasted/worn very well. Highly recommended!

    3. Count me in as one who’d be interested in wide calf boots. And a lot of current pairs look cheap, cuz the manufacturers must think that larger women lose their taste proportionately to their size.

  2. I feel for you ladies – I have the opposite problem. I have very skinny calves (and I am not a skinny person) and I have never yet found a pair of knee high boots that don’t flap around my legs as I walk. I do love thos Naturalizers though!

  3. So glad I scrolled down and saw the wide calf comments! I get frustrated by the lack of options for my thicc legs as well. Off to check out Duoboots!

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