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!


  1. My big question is where to find these jeans long enough…every pair Of boyfriend jeans I see are Capri length to begin with. Being just outside of Rochester NY I have the same problem of cold ankles….Thanks!

    • yes..I know…longer boyfriend jeans are harder to find..but there are some out there.!
      Shana…is that a pretty free people lace bra peeking out? 🙂
      going to copy this look tomorrow! cause thats what i do!
      Thank you

    • Tricia – the madewell jeans I linked to are long, as are many of jcrew’s or blank denim. I often end up just using straight leg jeans as my boyfriend jeans because I like the fit better.

    • I just broke out my boyfriend jeans for the first time this winter to take my daughter to the Strong Museum’s Royal Ball! 38° felt like a warm spring day after this winter.

  2. I’m not feeling the way the jeans look slouchy at the top of your boots. Looks kind of 90s hip hop-ish, especially with the Timberland-yellow colored boots. I think boyfriend jeans need to just hang at the ankle. I would do a really low cut ankle boot and cuff the jeans just above. Definitely not as warm, but truer to the effect of boyfriend jeans. Otherwise, they just look like baggy jeans. Aside from the critique, I have searched Pinterest for the exact same thing- winter boyfriend jeans ideas- and been totally annoyed. Winter in Savannah, maybe.

    • Agreed. Not my favorite look.. Tho I appreciate the effort! I have been trying to figure out how to make this look more chic bc this IS what I typically look like in winter.. Baggy jeans so my long johns fit beneath, no heel, waterproof Keens, several layers on top.. Spring will be better!

  3. Can we get a few details about you hair? I’m due for a cut as my long pixie/short bob? is way over grown. Are you still air drying – even though the thought of air drying the in the ccccold is too much for me to bare!

  4. Sigh. *Love* this French connection coat but “final sale” is such a buzzkill! Beautiful jewelry! The polished/slouchy mix gets me every time. So good!

  5. I’ve struggled with the same concept of wearing boyfriends in winter. Heels in CO just ain’t happening. Thanks for giving this a try!

    Is the Madewell Transport Tote new? Do you like it? I’ve been debating on getting one. Would love to see a bag roundup soon.

  6. I think all those people who have bare ankles must spend winter in LA. It was 90+ here in SoCal today. Craziness. I’m not ready for summer yet!

  7. Hi Shana! I’m back!! I have a lot to catch up on over here on TME. Looking forward to it.

    And….I couldn’t agree more! I want to look so cool in heels, but they are sooooo impractical. But, you are very right! A bootie makes me feel like I’m in a heel–even though they’re super comfortable. In fact I’m wearing a pair to work right now. I swear by my DV Juju. Great purchase! Then with my old pair from last year, I turned them into sparkly ones. Although, I prefer your glittery ones from a post this past December. (Hmm….I wonder if they’ve gone back on sale now…?) I think that was right when I found you. I’ve been in love since:D


    Ann of Kremb de la Kremb

    • I just gave a solid hunt for the BCBG Charm in bronze but to no avail. Only available in silver and black. I have a black pair from Zara, but they just don’t tickle my fancy like your bronze do. Let me know if you have any tricks up your sleeve–oh and hey! Do you sell your stuff anywhere? I’m a 37 if you’re done with them;D A x

  8. Just came across this post as this is a problem for me as well – the way to do it is to not let your jeans touch your shoe, when they do it becomes decidedly masculine. A better way to do it is to roll or cuff your jeans up enough that a sliver of sock shows. It really is cute and fresh looking – though you really need to have the confidence to rock it. I’ve even worn rolled up BF jeans with wool socks and heels, that looks pretty cool too and a bit French. But I do have to agree with some of the girls above, it just looks so heavy when the jeans come all the way down to a heavy shoe, too masculine. A way to fix it would probably be to wear something very feminine on top….. Gwen Stefani-esque. Anyways, LOVE you blog.

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