How to Pair Pencil Skirts with Boots

How to Wear Skirts with Boots

While I’m still sizzling in Florida there are plenty of climates quickly cooling down as FB reader, Julie, mentioned the other day. Instead of diverting straight to your pants, consider pairing skirts with boots/booties. How to style them, Julie inquired, and here’s the answer. Check out these four ways to pair pencil skirts with boots, primarily for the office. Opt for chic and classic. I recall a former colleague wearing cute Coach booties with chain detailing that made noise every time she walked. (Trust me: you do not want to be that girl!). Walk in your booties — on tile, not the store’s carpet — before you commit, and then enjoy them.

Boots are perfect and all of the ones above can transition so easily from office to weekend, paired with your favorite skinny jeans (tucked in or cuffed above booties), boot cut or flares, and definitely with dresses or minis. If you forced me into booties with sparkle, these are currently my #1. Obsession city.

leopard skirt with black leather ankle boot (major look for less of these!) or black knee-high boots (1/2 off!)
faux leather oxblood skirt (mini version!) with cognac knee highs (flat riding boots for less) or wedge booties (in three colors)
scribble black and white pencil skirt  with black or grey wedge booties (love!)
black pencil skirt with black boot or grey ankle boot


  • Reply
    October 11, 2012 at 4:14 PM

    Alyson, you inspired me! I went online and got the Target Kamoni wedge in black, and because I am a sucker for the “buy one, get one 1/2 off” deal they were having at the time, also grabbed the Kaelyn bootie in taupe. Was a bit worried about quality but was surprised at how great they both looked when they arrived–and get this: both are comfortable as well as cute. Thanks!

  • Reply
    Stephanie Gerber
    October 5, 2012 at 9:07 AM

    I find it tough to wear pencil skirts with boots, but I do love them with booties!

  • Reply
    October 4, 2012 at 6:27 PM

    This is such a great post, Alyson – love those little wedge booties! 🙂

  • Reply
    October 4, 2012 at 6:14 PM

    Great post as I have 2 new pencil skirts and a pair of new riding boots waiting for the temps to dip!

  • Reply
    October 4, 2012 at 4:57 PM

    Oh, how I love boots! I am so happy it is boot season…about the only thing I like about cooler weather 🙂

  • Reply
    October 4, 2012 at 4:04 PM

    Pinning this post for some style inspiration later! Thanks!

  • Reply
    Kirstin Marie
    October 4, 2012 at 1:10 PM

    I love this idea. I really, really, REALLY want it to get cooler outside so I can wear my tights without sweating!

  • Reply
    Katie Cramer
    October 4, 2012 at 11:06 AM

    LOVE the black & white pencil skit! Definitely running to Ann Taylor to check it out!

  • Reply
    October 4, 2012 at 9:07 AM

    I really like matching my shorter booties to the color of my tights – it does work wonders at lengthening!

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