Our readers always want to know about the most stylish boots of the year, so we regularly dish out a ton of recommendations every fall and winter. This time around, my favorite trend is riding boots. They solve my biggest annoyance with boots: as a tall person, I never seem to find the right length of jeans to skim the top of ankle boots. But with riding boots, you just grab your favorite skinnies and tuck them in—easy as pie.
Clearly, Angelina Jolie is also on board with the riding boot trend. She recently wore Tod's Timeless Boots ($1295) with an all-black outfit—mask included—for a shopping trip in Los Angeles. I love that "timeless" is right there in the name of her boots because they are, in fact, classic. Scroll down to shop Angelina Jolie's outfit and other pieces to copy the look.
On Angelina Jolie: Everlane The Organic Cotton Box-Cut Pocket Tee ($18); Tod's Timeless Boots in Black ($1295); Valentino Roman Stud Nappa Chain Bag ($3350); EvolveTogether Milan Face Mask ($9 for 7-Pack)
Shop Angelina Jolie's Outfit:
These tees have a cult following.
These beautiful boots will last you for years and years.
It's not a celebrity outfit without a new designer It bag.
Tons of celebrities are wearing these practical triple-layer masks.
Shop More Riding Boots and Skinny Jeans:
Next, an expert told me the 5 most soothing colors to wear right now.
Opening image: Getty Images
-
*Not* Brown Suede: Everyone With Taste Is on the Hunt for This Dated Winter Boot TrendGrab a pair before it's sold out everywhere.
-
Every Fashion Person Has a Version of These 6 Night-Out LooksHow to reply to "What are you wearing out tonight?"
-
These $50 Old Navy Zipped Boots Are Just as Chic as the $1500 Pair I Have Been Coveting Since Last WinterThey're on sale for $30 right now.
-
Looking Chic in Cropped Jeans This Winter Means Wearing This Boot Style and ColorElizabeth Olsen would know.
-
The 2026 Version of Skinny Jeans Is Here, and I Tried It On—This Is Why It's a Game ChangerThere's nothing dated about it.
-
My Sister Asked Me What She Should Buy From Amazon—30 Fashionable Items I SuggestedBasically, everything on my Black Friday wish list.
-
Elizabeth Olsen's The Row Boots Are Chic, But These Ones Cost $1360 LessIt's girl math.
-
It's My Job to Find Wardrobe Staples, and These 35 Pairs of Black Boots Are ItWe're talking everything from sleek knee-highs to classic riding boots.
