One of the amusing things about this day and age is that nearly every style of jean works. When I was in high school, the idea of wearing anything that even resembled a tapered leg was an atrocity (hence why we all sported a "boot leg" cut). But now it's completely different. Whether you want to wear something high-waisted with a wide leg or a skinny jean with a dark wash, it's all up to personal preference. I'm a big fan of a boyfriend jean, one that's a little relaxed, but still fitted and like you've borrowed a look from the guys...without actually looking like one. With that in mind, I test drove eight different brands (cuffed twice at the bottom) to see which ones I liked best.
Madewell "Boy Jean" - size 26 ($115): This style had a bit of a mom jean vibe going for it, but not necessarily in a bad way. The color was pretty one dimensional with little discoloration. The fabric is stiff with little stretch with a slightly narrower leg.
Rag & Bone "Boyfriend Jeans" - size 26 ($220): These turned out to be my favorite pair for a variety of reasons - they're incredibly soft with a nice, worn-in feel. There are well-placed rips on the knees as well as an in-between color wash that I like. They're not fitted, but still manage not to feel baggy.
DL1961 "Riley Boyfriend Jeans" - size 27 ($168): These are so thin and soft that I would almost recommend also wearing these to bed. I like the '70s-esque faded cornflower blue and how they sit lower on the hips - they feel fresh and perfect for spring.
Gap "1969 Sexy Boyfriend Jeans" - size 4 ($69.95): Since my favorite pair of boyfriend jeans are by Gap, I was a bit disappointed in the look and feel of these. They're incredibly stiff, so perhaps I could break them in, but I also wasn't a huge fan of the unnatural-looking rips placed on the legs and the longer crotch that felt a bit too borrowed-from-your-boyfriend.
J.Crew "Vintage Straight Jean" - size 26 ($139.99): To begin, I'd recommend getting one or two sizes smaller than you'd usually buy. A medium wash with zero stretch (which I like) and a feminine, but loose fit.
Current/Elliott "The Boyfriend Jeans" - size 27 ($229): These were really comfortable with a wider fit. I like how they almost take on an ombré-like coloring, but could have done without the extra-wide opening at the ankles.
Old Navy "Cropped Skinny Boyfriend Jeans" size 4 ($19): With their higher waist, tighter fit at the bottom and structured but not thin fabric, these were surprisingly great. Though they had zero holes or discoloration, I liked the unexpected cream-colored stitching.
McGuire Denim "Mrs. Robinson Jeans" size 28 ($218): These were a slimmer take on a boyfriend jean that fit true to size with good fading. I'd never heard of this brand before, but like how this pair of denim could easily go from day to night due to the really tapered ankle.