Revisited Latest Trend- Shoes to Wear with Cropped Flare Jeans

Revisited Latest Trend- Shoes to Wear with Cropped Flare Jeans

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Grey embellished sweater for over 50 women

Revisited Latest Trend- Shoes to Wear with Cropped Flare Jeans

I’m showcasing shoes to wear with cropped flare jeans per a request from Gail. Both Lesley and Charlotte gave options with other kinds of shorter pants. And I wanted to revisit this pair of jeans that I showcased last October.

Quote of the day: “If you want to live a life you’ve never lived, you have to do things you’ve never done.” Unknown

The quote reminds me of the saying about doing the same thing over and over and expecting different results (which is the definition of insanity, right?).
And it’s no different with clothes. If you’d like to feel better about your style, you can’t expect to buy or wear the same things and look any different.

So even if you think the latest trend of cropped pants would be terrible on your body, you won’t know until you try!

Insider tip: Remember, not every item “categorized” as cropped or any other adjective is created equal. Which means, if you try on one pair and hate them, don’t think that every pair will be the same. The details, cut, material and sizing can make a HUGE difference.

BTW, in the original post with these pants, I wore all different shoes, yet mainly the same styles. This post I’m including a wild card option that I wouldn’t normally wear.

Jodie’s Outfit

White cropped flare jeans

Pants: Ann Taylor~~ Sweater: Catherine Malandrino~~Hat: thrifted (worn due to a bad hair day)

I bought these cropped flare jeans when there was an incredible sale on them for less than $20. The only reason I succumbed to the sale was I had put on some weight and wasn’t fitting into this pair of ivory culottes that I had from years ago.
The original pair was categorized as “culottes” and they are a silkier material plus not as flared at the bottom. Yet, even though both pair are marketed with different descriptions, they are very similar.

So let’s get on with my ideas of what shoes to wear with cropped flare jeans.

Spoiler alert–I really think ANY style of shoes go with these pants. I feel like we need to stop obsessing over those “rules” that this style cuts your leg off or this vamp isn’t flattering!!
Enough with that, and just have fun with the clothes!!
So I showcased not only different color shoes but 6 different styles.


Since both of these boots are SO similar, I wanted to show them side by side. But these cropped flares are perfect for wearing your tall boots or booties. With both of these options, you can show off the boots since they aren’t hidden under the pants material.

The tall boots are a recent purchase from Macys and the booties are Walking Cradles. Obviously I love the snakeskin pattern and think it goes with so much in my closet.

White Sneakers as Shoes to Wear with Cropped Flare Jeans

Most of you are comfortable matching your pants to your shoes. So it should be no different even with a cropped pair of pants.
I decided to wear my espadrille sneakers for this outfit, but in my original post with these pants, I wore blue ones!!!

Insider tip: Sneakers come in all kinds of styles and shapes. Don’t cross them off your list with “dressy” pants because they can look like regular shoes many times.


We all have heard how every woman should have a pair of nude shoes to “elongate” the leg. Depending on your skin tone, that pair of shoes could also be blush colored.
I had picked out a pair of sandals and mules to go with these pants, and realized how similar they really are.

The sandals are from Naot which I won from an Instagram giveaway and the mules are J.Jill.

Insider tip: Want to win giveaways on Instagram? I have the post on what to do and how to do it.

Wild Card

My combat boots are finally getting more love from me, but they certainly weren’t part of my initial thoughts of what shoes to wear with cropped flare jeans.
Yet, when you analyze them, they are basically an ankle boot. Sure, they are a “heavier” shoe or “clodhopper” as my mom likes to call them. Yet, Lesley also paired a heavier shoe with her cropped pants.

Do they work? Of course my answer is YES!!

Other ways to style masculine footwear
Exploration of 5 Ways of How to Wear Combat Boots
Using My Imagination For 5 Ways of Styling Brogues

Shoes to wear with cropped flare jeans

Photo credit: Rob Filogomo

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