How To Wear High-Shaft Booties With Jeans

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As many of you may already know, I’ve been a fan of PAIGE’s Willa booties for months now. I bought them in snake print this past winter, so was thrilled to see a studded version in this year’s Anniversary sale. When I first introduced these higher-shaft, Western-inspired booties on TME (here and here) we got a bunch of questions about how to pair them with jeans. Because of the higher shaft (yet very walkable heel height) it was…tricky. Do you tuck skinny jeans into the top? Pull the jeans over top of the boot? Should you even be wearing skinnies with these booties??? WHAT.

In response, I threw together a little video explaining why one might have trouble pairing these boots with skinny jeans, how to fix it, and the one style of jean I personally think were MADE for these boots.

(Eagle-eyed readers might wonder why I’m publishing a video with turtlenecks in July. If you MUST know, we filmed…and then got totally overwhelmed by spring and end-of-school-year craziness, and by the time I was like OH, THE VIDEO the weather was warm. So we planned to drop it in the fall….and then the Nordstrom Anniversary Sale happened and THE BOOTS WERE IN IT. So here we are.) 

How I’m Wearing High-Shaft Booties With Jeans

In case you are wondering, here are the pieces featured in the video:

PAIGE Willa Booties in snake print – not part of the NSALE, but they come in two different snake prints and both are GORGEOUS. These boots, BTW, run a bit narrow in the toes, so if you are between sizes, go up a half-size. Also, they will stretch out with wear. I love mine enough to travel in.

PAIGE Willa Booties (studded) – the exact same boot, but on major sale (until Aug 4th, then prices go up). I can’t decide which color I like better…but for some reason, I really want the brown to work.  

AG ‘The Legging’ Jean (size 25) – these are the first jeans I try on in the video. Lower rise.

AG ‘The Farrah’ Jean (size 25) – exactly the same jean as ‘the legging’ but with a higher rise. Some of my most-worn denim right now.

MOTHER Tomcat Jean (size 24) – my wash is long gone, but I actually like the one I linked too (with a cool bit of distressing) better. 

Equipment Turtleneck Sweater (xs) – forever and always my fav.

Z Supply T-Shirt Dress (xs) – one of my fav t-shirt dresses. Runs pretty short though (but I like it like that).  Size up for a bit more length.

Hope this helps!

xo,

S

P.S. This one’s for the Pinners!

Styling jeans & boots = hard. Add a high-shaft to ankle boots — complex. Our how-to video for skinny & straight-leg jeans with my fav snake print booties.

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About Author

Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and shorts known as denim-underwear, always.

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7 Comments

  1. All good, but I’m going to make a pitch for matching Paige Willa booties with high rise flares–my new favorite combo.

  2. Great video. I also wear my higher-shaft booties with my cropped demi-boot styles, like the Madewell Cali Demi-Boot jeans, and cropped wide-leg styles. No leg showing — I think they look great and it’s a way to keep wearing these styles into fall and winter. Does TME approve?

  3. I totally agree with Elisabeth. My Cali Demi-boot jeans are in heavy rotation now with sandals, andI think the higher, shaft boots will be my go to with the Cali jeans this Fall.

  4. Elizabeth Rafter on

    Love this! Those boots are amazing and look great with all of the jeans. I will pray to the denim gods, though, that we stick with high rise jeans from now on!!! 🙏🏻 So much more flattering!

  5. I’m with Elizabeth; high-rise FOREVER. I love, love, love seeing these styling tricks videos! I would really enjoy seeing more of them, from a few people – like could you and Laura and Tiarra all style the same/similar cut of denim with the same/similar bootie shape/shaft and show us the shirt/top options that work best with each person’s shape? I buy so many of the pieces recommended here, and I love them dearly, but I get in real style ruts sometimes and I love seeing how a new mixture of pieces can look totally fresh and how it works in real life on real people. I guess what I’m asking is….more “How to wear X with X” style advice, please? You’re all so great at it!

  6. Hi there! What else do you style that Z Supply side knot dress with? Denim jacket and athletic shoes, obviously…but I found the pairing of it with the denim and boots interesting! Any other interesting suggestions?

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