Fashion & Style

Style Rx: How to Rock Boots with Skirts!

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In case you missed it, I started a new series called ‘Ask the Style Medic’ where you can send me your style, fashion, wardrobe, shopping, or money saving (it is my super power you know) questions.

So let’s kick things off with this question from Allison:

“What are appropriate boot/skirt height ratios? For example, what lengths work best for booties, over the knee/thigh highs, and mid-calf boots?”

Here’s my answer:

It’s definitely boot season so this question is right on time! Boots are one of my favorite fall/winter wardrobe staples. Boots can be sexy, stylish, or casual (or all three!). They can be dressed up or down and paired with a bunch of different looks.  Although most women will just rock them with jeans or pants, boots definitely play well with dresses and skirts. Keep reading for How to Rock: Boots with Skirts:

Watch the hemline: The most flattering look for boots worn with skirts is to keep the hemline (bottom) of the skirt higher than the boot. Basically, you want to have a little peek of skin between the skirt and the boot. Obviously this isn’t a big deal with maxi skits.

Mini – Go ahead and rock boots with your mini skirt or dress but pay attention to the heel and boot shaft height. You don’t want to look like Julia Roberts on Pretty Woman. Go for mid-calf length to dress it down or booties to dress it up.

Midi – The best boot pairing with mid length skirts is an ankle boot. Depending on the skirt length, you could also rock a knee or thigh high boot.

Maxi – If you’re rocking a maxi skirt, the type of boot isn’t as important as the heel height. Rock a higher heel to avoid looking too casual or frumpy.

Keep out the cold: As the temps continue to drop, it’s just good fashion sense to pair your skirts with tights for a little warmth. You could add an extra dose of personality with funky colors and prints. Some tights are even fleece lined to make them even more warm and toasty.

Dress for the occasionWhile a good pair of boots can take an outfit up a notch, not all boots are created equal. At work, for example, you might get away with rocking a pair of heeled ankle boots or knee boots, but thigh-high versions may be a little risqué. Also, unless your workplace is super casual, I’d avoid wearing Uggs or similar weekend friendly styles.

Pick a star and let it shine – If your boots feature studs, zippers or other adornments, let them be the star of the outfit and keep everything else simple. You don’t want to overdo it. 

Now that we've gotten that all taken care of, here are a few styles to get you started: How to wear Boots with Skirts

(1-8) ShoeDazzle ‘Mayar’, $55.95 | Buckled Ankle Strap Booties, $34.90 | Steven by Steve Madden Wedge Boots, $106.40 (sale) | Shoedazzle ‘Aaliyah’, $39.95 | Shoedazzle ‘Calli’, $49.95 | Shoedazzle ‘Aurora’, $45.95 | Sam Edleman ‘Keaton’, $149.95 | Pointed Metallic Booties, $34.90


What say you? How are you rocking boots this season?

Do you have style, fashion, wardrobe, shopping, or money saving  questions? Send them to me HERE



**This post contains affiliate links. That means that I may get a commission if you decide to make a purchase using these links. All opinions are my own.**


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T. Espinoza is CEO at The Style Medic. She's the Diva next door, the girlfriend who always looks Fab but doesn’t spend a bundle. She works with the active, focused Diva who wants to look fly, save time and most of all, save money. T. can help you streamline your wardrobe, maximize your budget and take your style from flat-lined to FABULOUS!


  1. Allison


    Whoo hoo! Now I just need to find some more skirts to rock with all my boots!

  2. Great tips! I'm all about the ankle boot right now. Love the pointy metallic ones listed!

    Thriftanista in the City recently posted…{Thrift Haul} Goodwill vs. RetailMy Profile

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