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.