When American Eagle introduced the “boyfriend jean” back when I was in high school, I was dying to try a pair out. Half because I liked the idea of having a boyfriend (no, I didn’t actually have one) and half because I always envied how laid back and comfortable my guy friends looked. Meanwhile I crammed and wiggled my way into bootcut jeans every morning, longing for those magical pants that somehow looked loose around the legs but hugged all the right places.

Then I tried a pair on.

M.I.S.T.A.K.E.

How those American Eagle models managed to look feminine and confident in those pants, I will never know. I looked like a construction worker taking his lunch break.

The boy pant is still something I struggle with today, and a look that I envy every time I run across it in magazines or blogs. But I think I’ve figured out a way to make it work in real life, without the help of Photoshop. Today, I would love to share these tips with you, in hopes that I’ll see more women confidently rocking this look, so maybe I feel brave enough to try it myself.

1. Cuff ’em and wear heels. Seriously. Wonder how you’ll get those long legs? This is the trick. I especially like the idea of just wearing a casual t-shirt and letting the heels be the only dressy accessory. This is probably one of my favorite looks ever.

2. The more holes and the more inseam, the better: Never wear boy jeans down low on your hips, pull them up, cinch them with a belt and make them look as worn in as possible. By wearing a soft floral blouse and heels you can make the somewhat sloppy pant situation look absolutely fantastic.

3. For casual occasions, don’t be afraid to embrace the slouchiness: If you’re headed for a weekend grocery shop or a midweek coffee break at Alterra, wear a light wash jean and an oversized sweater or this chambray shirt.

If you’re looking to complete one of these outfits without the help of your boyfriend or your guy friend’s closet, here are a few pairs that are on my wishlist:

Gap 1969 boyfriend jeans – $69.95, for dressier occasions

Madewell boyjean – $125.00, for just knocking around

Urban Outfitter’s colored jean – $100.00, for when you feel extra gutsy

And of course, the jean that started it all, that ironically doesn’t look so boyfriendy anymore and that I would never want to actually see on my boyfriend. Thanks American Eagle.