Denim Tips: Pair Your Boy Jeans With Bossy Heels

I just love a good contrast, don’t you? I think my very favorite thing about styling my denim (that comes especially easily in the spring months) is dressing up casual, washed-out, distressed denim, and dressing down slick, fitted, dark denim. Same goes for mixing up masculine and feminine pieces.

If you know me personally, you know that I have this crazy dream that someday I’ll be a girl who wears heels all the time – with ease. It’s as if I think one day I’ll just wake up and tadaaa I’m wearing stilettos and wedges daily and feeling fantastic. While this may not actually happen, I am making strides when I can, to give my flats and loafers a rest and elevate my style, if you will.

The latest incarnation of this dream for me, is pairing perfectly slouchy and distressed boyfriend (or just boy, if you’re feeling trendy) jeans and seriously amazing, killer, you-can’t-not-look-at-these-shoes shoes. Give me colors, give me all kinds of straps, give me excess. I’m ready. All you need to complete this kind of look is a slouchy tee (like this), or silk blouse for the office, and simple, structured blazer.

How I envision pairing them:

1 .J Brand Aidan Slouchy Boy Jeans + Rag & Bone Apollo suede sandals

2. Current / Elliott The Boyfriend Cropped Jeans + B Brian Atwood Luciana Fringe sandals

3. Madewell Destroyed Indigo Boy Jeans + Elizabeth and James Sam T Strap heels


[Image credits: Capture The Castle; The Sartorialist; Sincerely, Jules]



  1. April 3, 2012 / 12:06 pm

    This is easily one of my favorite combos. There’s just something so effortlessly cool and sexy about the mixture.

    Rebecca (hearts)…

  2. April 3, 2012 / 2:27 pm

    Such a great combination!!! Too often, I pair my bf jeans with sloppy flip flops or flats. Need to dress ’em up!

  3. Leslie H
    April 3, 2012 / 7:25 pm

    the use of “bossy heels” is amazing. great post!

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