Wearing Cropped Jeans With This Type of Shoe Keeps Them From Looking Dated

Ah, cropped jeans. They used to be a non-controversial wardrobe staple, but these days, there's much debate about whether or not they're "in." I happen to be of the thinking that cropped jeans remain a wardrobe staple, even though full-length jeans feel a bit fresher these days.
What keeps cropped jeans looking current is what you wear with them, and Katie Holmes just provided a great example while walking around NYC. Holmes wore her wide-leg cropped jeans with an oversize plaid shirt and black scarf, but it was her shoes I was drawn to. Holmes opted for ankle boots that were high enough to be covered by the hem of the jeans. If you ask me, cropped jeans look the chicest with shoes that don't show any skin between the shoe and the hem of the jeans. It's subtle, but it makes a difference—trust me.
With that, keep scrolling to shop cropped jeans and mid-calf boots to wear together.
On Katie Holmes: Khaite bag; Saint Laurent boots
Shop Cropped Jeans
Shop Mid-Calf Boots
Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
I Found a Trove of Cool-Girl Basics From the Nordstrom Sale—31 Chic Standouts
These have closet-staple status.
By Jennifer Camp Forbes
-
It's Here: The 2025 Version of Skinny Jeans
Spotted on Emily Ratajkowski in NYC.
By Allyson Payer
-
35 Incredibly Chic Luxury Finds I Would Immediately Buy If My Salary Tripled Tomorrow
A girl can dream, right?
By Jennifer Camp Forbes
-
I Own $500 Jeans, But This Under-$150 Pair Looks and Feels More Expensive
Trust me.
By Nikki Chwatt
-
Not Black, Not White: The "Just Right" Sneaker Color Everyone in Fashion Is Wearing
Get on board.
By Nikki Chwatt
-
I Tried This Curve-Friendly Denim Brand for the First Time—These Are the Jeans I'm Wearing Now
Everything you need to know about popular Good American denim styles.
By Chichi Offor
-
Anti–Skinny Jeans Are Still Ruling in 2025—Finally, 15 Fresh Ways to Wear Them
Stealing these looks this season.
By Michelle Scanga
-
Amal Clooney's Croc-Embossed Thigh-High Boots Are About to Cause a Stir
Guaranteed.
By Erin Fitzpatrick