2013 / Tutorials

4 ways to wear jeans and heels

A while back, a reader suggested I write about wearing jeans and heels. Since my daily uniform generally consists of this combo, I figured a post weighing in on the trend was long overdue! I’m so excited to share four ways I pair the ultimate casual staple with heels.


I always pair loose fitting boyfriend jeans with classic heels like pointed toe pumps. The key to avoiding a sloppy look is balancing the masculine denim with feminine heels. Classic, simple shoes are your best bet — avoid platforms and complicated embellishments. I recommend a clean, tall cuff with the fold grazing the backs of the heels.


I try to keep things extremely simple with patterned denim, pulling one color (here, nude) from the print to coordinate with the heels. Don’t be afraid to let the lining show, I think it keeps things interesting and helps dress down the heels. A small cuff also creates a natural break between the pattern and heels, all while showing off your ankles!


You have plenty of creative range with skinny jeans. This popular fit is much less complicated than other shapes, naturally lending itself to a wide range of heel styles — classic pumps, sling backs, ankle straps and booties. I love haphazardly cuffing my skinnies to add intrigue to the traditional fit (even if the hems are uneven) and to dress down structured heels.

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If all this cuffing is too overwhelming, try a pair of cropped denim. To reinforce the obvious retro feel of ankle-length trousers I gravitate toward 1950’s inspired heels like these cobalt sling-backs. This look is effortless — no DIY or folding required. Pair with a silk ‘pajama’ shirt or denim button-down for a no-hassle day-time look!

As with all of my advice and tips, I urge you to trust your instincts AND step outside of your comfort zone as you navigate this trend. Be sure to check out my Jeans + Heels Pinterest board for more inspiration and share photos of your jean & heel combos with me on Twitter and Facebook!


19 thoughts on “4 ways to wear jeans and heels

  1. Great tutorial. I type this as I look at my rolled skinny jeans 🙂 I’m glad you are showing options with a “cleaner” look around the ankles so that you can see the shoes! Remember flared and bootcut hems that just engulfed your entire foot and shoe?!

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  3. These are cute pictures. 🙂 There’s an infographic on Pinterest that I saw months ago, showing how to cuff, with what shoe. You should check that out, although I think your tips are spot on.

    xo Ashley

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  5. Great tips and perfect photos! I especially love your idea about creating haphazard, uneven cuffs. I had never thought of this and am definitely going to try it!


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