Thanks, bitches! Changed the shoe to a flat and went bare ankle. I knew I could count on you all! Answer from cookiethumpthump on reddit.com
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Pinterest
pinterest.com › explore › women's fashion
How to Wear Ankle Boots in Various Styles and ...
September 23, 2014 - There are various styles of ankle boots, and it’s better to know which way a boot can be worn with an outfit · My Style · 2.4k Pins · 2y · Boots With Capri Pants · Fitted Ankle-length Capris For Fall · Chic Ankle-length Capris For Fall · Capris In Winter ·
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Reddit
reddit.com › r/bitcheswithtaste › can i wear ankle boots with a cropped pant? or go bare ankle and a flat? neither?
r/bitcheswithtaste on Reddit: Can I wear ankle boots with a cropped pant? Or go bare ankle and a flat? Neither?
August 16, 2024 - That style of boot where it is really low is not on trend these days, most boots have a slightly higher shaft now for this reason. You would want the pant a little longer to hit the top of the boot or just over. As for a flat, it’s hard to tell from the picture how short the pants are, but you can definitely go slightly · cropped pant with bare ankle and a flat for sure.
Discussions

I need help with cropped pants + boots!
I think the big rule with cropped pants is that your boots are supposed to be taller or use a sock to fill in the gap. Showing a gap is a little dated right now. But you can also wear knee-high boots over pants again. That’s back. More on reddit.com
🌐 r/fashionwomens35
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January 17, 2025
Which shoes with these dark capri leggings: sock boots or booties

The ones without the buckle are much more modern. The buckle ones are giving “millennial showing their age” (from a millennial constantly showing her age)

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🌐 r/fashion
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February 25, 2022
[deleted by user]

As said in the main post, this is pretty niche, and kinda silly, guide overall. But hopefully it'll be of help to some.

If you notice any spelling mistakes or broken links please reply to this comment.

Also if you've appeared in the inspiration album and don't want to be included just shoot us a message and I'll be happy to remove.

More on reddit.com
🌐 r/malefashionadvice
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STYLECRAZE
stylecraze.com › home › for you › fashion › here’s how you style cropped pants with boots
Here’s How You Style Cropped Pants With Boots
November 18, 2024 - Ankle-length boots look amazing with capris. Also, these boots can cover the distance between the boots and the pants. Some thing wrong with illustration image shortcode.
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Pinterest
pinterest.com › wendyertel › cropped-pants-with-boots
Discover 9 Cropped Pants with Boots and how to wear ideas
13 Cool Ways to Wear Cropped Trousers With Ankle Boots | Who What Wear UK · Military Street Fashion · Hippie Mode · Unique Outfit Ideas · Boho Mode · 90s Fashion Outfits · Mode Casual · Crop Dress · Mode Inspo · Moto vest with capri culotte pants and boots ·
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ShoeTease Shoe Blog
shoe-tease.com › home › shoe styling › how to pair ankle boots with any style dress pants – a woman’s guide
How to Wear Ankle Boots with Dress Pants - A Woman's Guide
December 19, 2024 - Toe shape is also essential. Ankle boots with square or almond toes are great boots to wear with flared dress pants – especially longer ones – for a softer look under the pants.
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Fabulous after 40
fabulousafter40.com › home › best boots to wear with cropped pants & styling tips
Best Boots to Wear With Cropped Pants & Styling Tips - Fabulous after 40
September 17, 2025 - Now imagine wearing cropped, wide-leg pants that sit about 2-4″ above your ankle. There’s going to be a big chunk of your leg exposed. Ankle booties leave a gap between the top of your boot and your pant hem.
Find elsewhere
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Who What Wear
whowhatwear.com › home › fashion › shopping › shoes
12 Cool Ways to Wear Cropped Pants With Booties | Who What Wear
July 8, 2023 - Style Tip: The cropped silhouette helps to show off a statement pair of boots. Because why would you want to hide them? ... Style Tip: Black-and-white pieces make for some beautiful contrast that shows off your daring proportions. ... Style Tip: Pair playful patterned, cropped pants with some sleek, streamlined ankle boots for a standout look that is guaranteed to turn heads.
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Be So You
besoyou.com › home › which ankle boots actually work with jeans and pants in 2025?
Which Ankle Boots Actually Work with Jeans and Pants in 2025? - Be So You
October 30, 2025 - Learn how to wear ankle boots with jeans. See 7 outfit ideas showing which ankle boots work with wide-leg, cropped, and straight styles.
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Jess Keys
jesskeys.com › home › blog › how to style ankle boots with cropped pants
How to Style Ankle Boots with Cropped Pants - Jess Keys
November 19, 2019 - This typically means you’re going to need a boot that is cut a bit higher on the ankle–above the ankle, so it hits at the slimmest part of your ankle rather than right at the ankle bone.
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Houzz
houzz.com › discussions › 2416755 › how-to-wear-ankle-boots
How to wear ankle boots
Some younger girls can get away with high-heeled booties worn with bare legs. I don't wear high-heeled anything anymore so not for me! I very seldom wear panty hose anymore no matter what the season. Hate them. But I do wear tights. Matter of fact had on a knee-length slim skirt and suede Eileen Fisher low-heeled boots and a long sweater yesterday.
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Lookastic
lookastic.com › women › capri pants › ankle boots
Capri Pants with Ankle Boots Outfits (5 ideas & outfits) | Lookastic
Dial it down for the day in this comfortable combination of a black leather biker jacket and capri pants. Get a little creative with footwear and throw ankle boots in the mix.
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The Joy of Style
thejoyofstyle.ca › home › how to wear ankle boots with your pants – an easy guide
How to Wear Ankle Boots With Your Pants - An easy guide - The Joy of Style
March 21, 2024 - To this end, don’t pull skinny, straight or boyfriend jeans down over your ankle boots. Keep those hems ending above your ankle boots. This will create the styled and fresh look you are going for. There are many iterations of short booties: flat or heeled, fitted or wide open at the ankle, straight across the top or dipped at the front, above the ankle bone or below.
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Putting Me Together
puttingmetogether.com › home › uncategorized › how to wear ankle boots with pants for work – straight leg and skinny pants
How to Wear Ankle Boots With Pants for Work - Straight Leg and Skinny Pants
October 17, 2019 - Nothing extreme, but enough of a point to add crispness. A pointy toe also helps extend the leg line, which is especially helpful with straight leg or bootcut pants. 2. A skinny kitten heel. While most of us would rather wear flats everyday, sometimes you need a tiny lift for ankle boots to work well with pants.
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TikTok
tiktok.com › discover › capri-pants-and-ankle-boots
Capri Pants and Ankle Boots
November 17, 2025 - TikTok · Log in · Search · For You · Explore · Following · Upload · Profile
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Blundstone
blundstone.com › blogs › guides › how-to-wear-ankle-boots-with-jeans
How to Wear Ankle Boots with Jeans, Wearing Boots & Jeans - Blundstone
Cropped skinny jeans paired with ankle boots are a casual and effortless appearance. This is a great way to lengthen your leg while showing off your ankles. Check that cropped jeans hit right at the ankle bone so that they don't bunch up or ...
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Real Simple
realsimple.com › beauty-fashion › shoes-accessories › shoes › how-to-wear-ankle-boots
How to Wear Ankle Boots With Practically Every Outfit You Own
November 14, 2025 - Cropped jeans and ankle boots are a match made in heaven. Cuff the hems—instead of tucking them into the boots—for some major ankle action. The cropped hemline creates a frame for showing off your favorite booties.
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Macys
macys.com › macy's › women's fashion, shoes & accessories › shoes › booties & ankle boots
Women's Ankle Boots & Booties - Macy's
November 25, 2025 - Step into style with Women's Ankle Boots & Booties at Macy's. Explore our collection of ankle boots and booties now. Free shipping available! Shop now!
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Who What Wear
whowhatwear.com › home › fashion › outfit ideas
Wondering What Shoes Pair Best With Capri Pants? Your Search Ends Here
April 30, 2025 - Straddling the line between tailored trousers and shorts, capri pants demand thoughtful styling, particularly when it comes to shoes. The wrong pairing can throw off proportions or dull the look entirely. Are flip-flop sandals the answer? Perhaps a retro-inspired sneaker or a kitten heel?