The Perfect Boyfriend

Boyfriend jeans. Another thing that you can add to that list of things (like skinny jeans and block heels - also pictured here) that I thought I would never, ever wear. I held off for a while when boyfriend jeans first became popular, but when they appeared to be going nowhere any time soon, I caved-in and gave them a try. Okay, I get it now. They're pretty gosh-darn comfortable, and look cute rolled-up to showcase whatever shoe you're wearing; a look that has sort of come to define the second decade of the 2000s. However, I think it's madness that anyone would spend more than the $5 it cost me to grab this pair of "boyfriends" off the rack in the local thrift store (during my last trip to the USA). The boyfriend jean is essentially a sized-up version of the "mom" jean, and we all know how rife with such things thrift shops can be.

I wanted a pair in white because I wanted a second white pair of white jeans (my other ones are skinny), but find that white can really look quite "dressed" if the denim isn't distressed in some way. I figured the boyfriend style would be a good alternative to a distressed jean. I'm not opposed to distressed white jeans, but they aren't as wearable, and doubly-so in Scotland, where summer is more of a theoretical construct than an actual season.

This preference for a more casual white pant most likely stems from my many years working for a cruise line and having to wear crisp, perfectly turned-out white skirts. Those days are long gone; the uniforms of most cruise lines have gone the unfortunate way of the corporate polo shirt and a pair of Bermuda shorts. Eew.

But I digress. Still resisting the boyfriend jean but secretly want to give it a go? Don't spend a lot of money! Here are a few things to look for in your local thrift shop the next time you're out that way.

How To Not Spend A Lot Of Money On Your Boyfriends. 
Insert your own joke here. 
  1. Look for that 80's cut; larger in the hips and thighs, tapered at the ankles. 
  2. Size up; one or two sizes from what you usually wear should do the trick. Remember that clothing from several years ago fits a lot smaller than same-sized clothing nowadays, so make sure to try everything on. 
  3. Choose a pair that has a flat front - no 80's front-pleats - bleah!
  4. Look for a waistband that is medium-high, but be careful; super-high waists can look strange once you size up…the crotch of your boyfriend jeans might be dangling between your knees in order to achieve that perfect loose-fitting look. 
  5. Make sure you choose a pair that still flatters your posterior, even in the larger size. Check for droopy rear pockets, baggy "crotchal regions" (to quote Ron Burgundy), and big gaps at the back of the waistband. 
  6. Do not fear wearing a belt, although they should fit well enough (before wearing them all day long) that you feel like you could get away without one. 
  7. Don't worry about the inseam. Boyfriend jeans are meant to be worn rolled anyway. Just be sure to try them on to make sure that the "roll" works at whatever length they are. 

Thrifted boyfriend jeans, similar / Gap tank / H&M shoes (last season), similar, similar (bargain) / Judith Ripka hearts ring / sterling feather bracelet (old), similar / sterling star earrings (old), similar


  1. Great tips. Can't wait to go shopping!!


  2. Ah boyfriend jeans....and I are NOT meant to be together. I tried my best last year to find a pair that fit me. But they were all too big in the bum, way too short in the leg so that rolling them turned them into pedal-pushers, or they slid off my hips at the least provocation. I'd abandoned low-rise jeans because I was constantly hiking them up...and knew I'd have the same issue with bf jeans. I still like the look...on you and others, though


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