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
-
Simone Ashley Is in the Fast LaneSince her breakout role in Bridgerton, our Spring Issue cover star has quickly risen to A-list status. Up next, she masters the rom-com leading lady.
-
The Spring 2025 Shopping Guide: Where to Buy the Biggest Trends of the SeasonYour short list of the season's key buys.
-
I Can't Wait for People to Quit Flats and Bring Back This Elegant Shoe TrendThere's simply no better style.
-
These Are the 7 Stylish Shoe Trends Fashion People Will Be Wearing With Jeans This SpringI see chic denim outfits in your future.
-
I Thought I Hated Skinny Jeans, But Kate Moss Just Made Them Feel Cool With This Shoe TrendSuddenly I need a pair.
-
So You've Heard Skinny Jeans Are Back—Here Are 6 Elevated Ways to Wear a Pair in 2025Bring on the compliments.
-
If a French Woman Shopped the Gap and Banana Republic Sales, These 30 Chic Picks Would Catch Her EyeOui, merci!
-
It's Official: French Women Love This Boot Style for SpringHere's how they are styling it.
-
When Sydney Sweeney and Lady Gaga Own the Exact Same Boots, You Know They're GoodGreat minds think alike.
-
7 Extremely 2025 Trends I'll Pair With Skinny Jeans and Leggings to Make Their Return Less ScaryWho's with me?
