Boyfriend Jeans: I Want To Wear Them With Heels, But My Life Doesn’t Support That


If you’ve spent any time on Pinterest, I’m sure you’ve seen some iteration of boyfriend jean styling that involves bare ankles and high heels.  Sometimes with slouchy, fuzzy sweaters, sometimes with blazers, sometimes with long tailored coats – I love it all.  But puzzling (at least to me) is how these outfits keep ending up on best-dressed lists called, “What You’ll Want to Wear All Winter!”  Or “The Best Way To Style Boyfriend Jeans When It’s Cold!”

I just…can’t.

I mean, even if I swap the heels out for some killer, sexy (yet walkable) flats….I still have a cold ankle problem to contend with.  But I’ve been drooling and swooning and desperately wanting to recreate these outfits….so…

The Challenge:  Come up with a way to wear boyfriend jeans now (with my Smartwool socks), but preserve that sort of I’m-not-really-trying-to-dress-up-but-I’m-so-totally-dressed-up vibe that this look is all about.

The Inspiration:


It almost doesn’t matter what pic I choose – there are so many similar variations on this theme.  But here’s the gist:


My Take:


The Shoe

For this, heels are a must.  I tried this look with several different iterations of flat shoes and came up with some cute options, but the vibe was decidedly different.  To get the look I wanted, I had to pair my boyfriend jeans with a pair of sleek, heeled booties.  But heck – boots like this are both comfortable (mine have a low, block heel – walkable, even when babywearing) and cheap.  I picked these boots up at DSW last winter for under $50.


The Coat

A tailored coat also helped.  It’s still too cold to go without one, and tons of layers + slouchy jeans + my short self is NOT a recipe for success.  Scaling back to a cool graphic sweatshirt and a tailored winter coat was the way to go.


The Details

There’s a lot going on, so I finished the look off with some pretty, understated jewelry.   The choker (or collar necklace?) and bracelets are by Another Feather, and are hand made in Portland, OR using recycled materials.  The nice folks at Zady sent me some pieces to see up close, and they’re pretty special (the copper bracelet is my fav – I’ve been wearing it alone almost every day for a little bit of easy glamour).




coat: French Connection Quilted Nylon Mixed Media Cutaway Coat c/o (size 0 for reference, but go up a size if you want to wear bulky sweaters)

sweatshirt: long gone, but Banana Republic’s Tomboy sweatshirt is pretty great (see more of my fav graphic sweatshirts here)

boyfriend jeans: old Goldsign for JCrew, but Madewell’s Patched Slim Boyjean is so similar (patches are my wintertime rips)

boots: Guess from DSW…Yoox has a very similar pair of tan suede ankle boots with a wood heel, and 6pm has a bunch of similar pairs on sale – my top picks would be these Loeffler Randalls (so sleek!!) or these heeled chelsea boots by Frye or maybe even this pair from Aldo (although that heel is looking a bit too high for me)

bag: Madewell Transport Tote

jewelry: Another Feather Pearl Collar Necklace and bangles, Gorjana stackable ring set (gold and silver mixed)

sunglasses: Ray-Bans

on Pax: Splendid hoodie (mine has lasted through two boys, and has remained one of my favorite pieces EVER), Braveling tights (yes, you read that right…he wear tights EVERYWHERE), sunglasses (they’re polarized and bendy so they won’t break when he puts them on himself)

How To Do The Cuff

Boyfriend jeans are tricky to wear with boots because the cuff of the jean interferes with the top of the boot.  Here’s my fav way to roll them for boots:

1.  Fold them up where you want them to hit (at the top of the boot, or just below the top)


2.  Fold the cuff back over top of itself (keep the top edge visible, it’s almost like scrunching…but you are actually folding in this step)


3.  Repeat on the other side, then scrunch a little to keep them from looking too perfect.


They don’t have to be perfectly even, the look is pretty haphazard.  And I have noticed that the cuffs inch down a bit as you walk around.  Because of this, I typically do this cuff an inch or so lower than I’m showing here (fully covering the top of the boot).  It holds its shape a bit better.





Ha ha just kidding.  Of course I’m going to round up coats – they’re my latest obsession!