Several weeks ago I decided to break out of my skinny denim rut and give boyfriend jeans a shot.  I don’t know about you, but trying on denim in stores is painful for me because (a) stores inevitably do not have the size you want (b) in the wash you want and (c) the sales people tend to be pushy about making you show them how they look but then are (d) completely incapable of being honest about how your backside looks.  My way around this miserable situation was to order almost every make and model of boyfriend jeans available through the great online clothing mecca, Shopbop.  The photo below shows only half of what showed up on my doorstep:

Several lessons were learned while trying on 30+ pairs and wearing the ones I ultimately picked (Citizens of Humanity’s Dylan Boyfriend).  To save you time and agony, my unscientific but completely honest research is presented here:

Lesson #1: Order one size smaller than your usual  – your normal size in boyfriend will swallow you whole.  This finding was consistent with every brand.

Lesson #2: Stay away from the wildly distressed versions to avoid looking like you’ve just painted a house or laid asphalt.  I remember reading in The Lucky Guide to Mastering Any Style half a decade ago that you can buy a pink jacket and you can buy a motorcycle jacket, but you should never buy the pink motorcycle jacket.  In shopping lexicon that means one statement at a time, my friends.  And I bet the denim sales associates would never tell you that.

Lesson #3: You may want to carry an emergency belt in your handbag as they seem to loosen up more than fitted jeans.  I was literally – embarrassingly – centimeters from being in a low-rider situation on my way to lunch one day last week.  And hiking them up only bought me a few strides before I had to do it again, and again, and again…

Lesson #4: Pair your new baggy denim with something a bit more fitted on top.  The following is a conversation shared with my almost-11-year-old daughter on a recent Saturday morning while she sat on my bed as I dressed:

H: Um, what’s with the mommy pants?

Me: They are NOT “mommy pants” they are boyfriend jeans and they happen to be VERY popular.

H: Popular where?

Me: You see street style photos and pictures in magazines of women wearing them with their heels and blazers all the time.

H: Then you should put on heels and a blazer or change back into your skinnies because you’re looking a little…down on the farm in that button-down.

It may sound like I regret my baggy-denim purchase, but I really am loving the relaxed silhouette.  And I confess to still wearing them with my button-downs, though only in our home or when well covered by a trench.

images 1 & 3 via tumblr, image 4 via Atlantic-Pacific