As I’ve said before, I love incorporating some androgyny into my style. There’s truly a bit of an art to pulling off a menswear look; whether you’re going full suit a la YSL or you’re literally just pulling pieces out of your significant other’s side of the closet, it’s important to be mindful of how items fit on your body type. As much as I’d like to steal more cozy pieces from my fiancé’s closet, alas I’m a slender-framed 5’9 gal and he’s a 6’2 grown man. The proportions just don’t work on most pieces. Enter the boyfriend-fit jean style, AKA The Boyfriend Jean.

It took me a long, long time to find the right boyfriend jean. Along the way, there were countless trials and errors, and some serious hesitation around throwing down more than a 100 bucks on a trend that I was already wavering on, as I was uncertain of how much mileage I could expect to get from such a piece. Finally, of all places, I found that Gap’s Sexy Boyfriend Cut denim fit great and didn’t break the bank. No, this is not some crazy flashback of the 90′s GAP. I was quite surprised myself, since I’ve had the worst luck finding any style of denim that fits properly from there in recent years.

But the point of this post is to not recount memories of Gap purchases from my high school years, but rather show you that you can find a reasonably-priced pair of boyfriend jeans that will get you a lot of mileage through versatile styling.

For part one of this three part series on how to rock the boyfriend jean, I decided to do an easy, sporty (take this with a grain of salt as it’s coming from probably the least sporty girl you’ll ever meet), girl-on-the-go and, in my case, work appropriate (start-up life…) look that is not only ridiculously comfortable to wear, but also exemplifies a laid back, yet clean and put together approach to dressing.

(Jeans: Gap, Sweater: Gap, T-shirt: Matt’s Vintage Nike T-Shirt, Boots: Kimchi Blue from Urban Outfitters, Belt: Banana Republic, Bracelet: Bridge Collection Cuff from Betsy & Iya Bag: Will Leather Goods)