Photo:
Beretta/Sims/Shutterstock
On Middleton: Penelope Chilvers Long Tassel Boots ($695)
This is a casual outfit formula Middleton tends to repeat often, involving a utility jacket, skinny jeans, and, of course, riding boots.
Naturalizer
Rena Boot
$250
These have plenty of glowing reviews on Nordstrom.
Tory Burch
Riding Boot
$648
$389
The sleekest riding boots for the city.
Photo:
Tim Rooke/Shutterstock
We’ve noticed how she sticks to dark neutrals with this combo. Black jeans and brown leather boots look so polished together.
Totême
The Riding Boot
$1130
It simply doesn’t get any chicer than this Totême pair.
Dear Frances
Saddle Boots
$930
These also come in black, since I know you were wondering.
Photo:
The Image Direct
Photographed at a horse show, Olsen wore traditional boots made for competition, but the equestrian trend can be worn well beyond the saddle.
Stuart Weitzman
5050 Leather and Neoprene Knee Boots
$750
The stretchy back on these ensures they fit like a glove.
Khaite
The Derby Boot
$1480
Only Khaite could make a pair of riding boots that are timeless and of-the-moment.
Photo:
Backgrid
Angelina Jolie wore Tod’s Timeless Boots ($1295) to run some errands in Los Angeles.
Proenza Schouler
Square Toe Riding Boots
$1395
$488
The square toe on these feels especially fresh.
Reformation
Kata Bucket Boot
$498
Classic riding boots with a little edge.
Photo:
Courtesy of Brandon Maxwell
Brandon Maxwell proved they’re the perfect match for your skinny jeans.
Naturalizer
Jessie Knee High Riding Boot
$180
The buckle details elevate this simple pair.
Franco Sarto
Meyer Knee High Riding Boot
$250
$105
The two-tone style is especially traditional.
Photo:
Courtesy of Tory Burch
Over-the-knee styles were spotted in full force at Tory Burch, styled with (drumroll, please) skinny jeans.
Proenza Schouler
Boyd Leather Knee Boots
$1397
$419
An investment pair you won’t regret.
Mango
Leather Boots With Tall Leg
$130
$120
A great under-$150 pair.
Photo:
@camillecharriere
Khaite’s Derby boots, pictured here, became a street style It item during the latest fashion weeks.
& Other Stories
Leather Riding Boots
$349
Simple perfection.
Sam Edelman
Penny Boot
$190
These Nordstrom favorites have a shocking number of good reviews.
Photo:
@fakerstrom
Grab a boxy blazer to re-create this casual-cool ensemble.
The Row
Grunge Calfskin Riding Boot
$2100
A minimalist’s dream pair.
Frye
Melissa Boots
$358
No one does equestrian boots like Frye.
Photo:
@jennymwalton
The boots are a favorite among NYC girls, too.
Stuart Weitzman
5050 Flat Boots
$295
An A+ pair from Stuart Weitzman.
Hunter
Refined Tall Matte Boots
$170