Because this super slim cut tucks right into boots, it was the first shape I used to transition my winter wardrobe to spring. Come warmer weather, I suggest rolling the cuffs over beat up sneakers. Click through to shop this style for every budget.
Kate Cropped Skinny Jeans With Ankle Zips in Vintage Civil 2 Wash, $89, guess.com
This works with everything my skinnier style does, but has a little more breathing room in the legs. Since it's such a classic style, I like to pair it with equally timeless shoes, like ballet flats or ankle boots. Click through to shop this style for every budget.
'Ava' Straight Leg Jeans (Mystic Blue), $228, Citizens of Humanity, nordstrom.com
Cropped Vintage Straight Jean in Indigo Foam Wash, $178, jcrew.com
Always make sure the shoe is chunky—pointy-toes and stilettos will read Hollywood circa 2003 in a very bad way. I like to wear something a little preppy up top, like a striped tee or cable knit sweater, to avoid any sort of boho cliché. Click through to shop this style for every budget now.
A slouchy cut in faded material can read sloppy if you don't take care with the rest of your outfit. Pair it with tailored boyfriend-y pieces, like a fitted blazer and brogues. Click through to shop this style for every budget.