How to Wear Ankle Boots with Skirts and Dresses This Fall

Making your ankle boots more versatile is a great way to maximize your investment (because boots aren’t cheap!) and make smart, efficient use of your existing wardrobe. But how?

One fabulous way to maximize your fall wardrobe is to pair your ankle boots with skirts and dresses. But while wearing boots with jeans is foolproof, wearing them with skirts and dresses is a little trickier.

pencil skirt and ankle boots
Pencil skirts don’t have to be all-business. Click to learn how to style your pencil skirts for less serious pursuits.
short dress and ankle boots
A nod to the 90’s…. Click to see how I toughened-up a demure dress for a modern take on the grunge-era favorite.

Here are a few simple tips to embolden you to make your boots work with something other than your jeans.

Tip #1: Socks

Socks, for most of us, tend to be an overlooked necessity in our wardrobes. For one thing, the recent trend towards no-show socks with sneakers and athletic shoes means most people never even see our socks. For another, another recent trend – applying state-of-the-art fabrication technologies to socks – is making them more and more expensive. As much as I appreciate how great my high-tech socks feel when I run, they don’t increase the quality of my runs any more than the socks I paid $3.99 for.

short dress and ankle boots

dress and ankle boots
Click to see more images of this look.

My $3.99 running socks might work just fine in my running shoes, but they don’t work with ankle boots. The good news is, you don’t have to spend a fortune to acquire a couple pairs of women’s dress socks to wear with your ankle boots.

Hue makes great socks in a variety of neutral colors for $4 per pair at For a little more money, you can buy high-quality cashmere wool socks from Brooks Brothers, which also come in a variety of colors.

In my opinion, no one ever needs to spend more than $25 on a pair of socks, but no one wants to peer inside the gapping top of your ankle boots, so one or two decent pairs of dress socks is a must.

Tip #2: Hemlines

I have yet to see a hemline that couldn’t accommodate an ankle boot; you can wear them with any length skirt or dress you choose, from the shortest minis to the longest maxi’s.

mini-skirt and ankle boots
Ankle boots downgrade an otherwise sexy look to a playful one. Click for more styling tips for your mini-skirts.
pencil skirt and ankle boots
Do: Wear boots with pencil skirts. Click for more.
midi dress and ankle boots
A formal dress gets the casual treatment with a denim jacket and ankle boots. Click to see how I put the look together.

Take the time to experiment with ratios and proportions to find the combinations that work best for you and are most flattering. If your calves are the envy of an NFL linebacker, try a high hemline like a mini skirt to elongate your legs. If you’re on the short side like me, a tea-length or midi hemline with a defined waistline can help you look taller, your legs longer.

There are no rules and no one-size fits all!

Tip #3: Take Photos

Being a blogger and having to look at hundreds of photos of myself has taught me the power of a photograph to illuminate the best – and the worst – details in an outfit. If I had a dollar for every time I scratched a look after seeing it in photographs, even though it looked great in the mirror, I’d have, well, about $100. I don’t know if it’s in our heads, if our sightline to our own mirror image is distorting, or what, but whatever the cause, mirrors alone are not always reliable.

dress and ankle boots
For more tips on layering sweaters over dresses, click on the photo.

Whether your snap a pic of yourself in the mirror with your iPhone or get a friend to take one for you, get photos of yourself in ankle boots with various skirts and dresses before judging a look based on how it appears in the mirror. You’ll be surprised to see what works and what doesn’t.

When I was preparing outfits for this week’s photoshoots, I was quite surprised to see how Western-inspired a favorite pair of ankle boots are. I tried them with several different outfits and each time I thought I’d found the right combination based on what I saw in the mirror, I’d rethink the look after seeing it in a photograph. All I could see was “cowgirl”. I still love the boots and will wear them with jeans, but I have yet to find the right way to style them with a skirt or dress.

Tip #4: Balance the Message

In general, boots are statement-makers and can have a high impact on an overall look. Black ankle boots automatically lend a little tough-girl edge to any outfit, while low-heeled suede varieties tend to give off more of a hipster or boho vibe.

What this means is that boots work best when they provide contrast. A good example of using boots to set up a contrast is the grunge-era look of the 90’s: A babydoll dress with black, lace-up Doc Martins. There’s a reason the look is making a comeback. Juxtaposing a coy, flirty, or ultra-feminine with look with a pair of badass boots is more mysterious and alluring than delivering a one-note message.

mini-skirt and ankle boots
Don’t think you can pick up your kids from school in a mini-skirt? Think again! Click for tips on how to style your mini-skirts for day.

Mini skirts, for instance, are youthful and sexy, which is great for date night with my husband, but not the look I want when I pick my kids up from school. By topping my red mini skirt off with a prim collar, tomboy sweatshirt, and flat ankle boots, I turn the volume down from “sexy” to “playful”.

In a similar way, this zebra print dress would normally be way too formal for day. Adding a denim jacket and heeled-boots, however, brings it squarely into the zone of elevated casual style.

midi dress and ankle boots
Midi-dresses and ankle boots are fast, fabulous friends. Click for inspiration for styling your date-night dresses for daytime affairs.

Again, experiment. Trying using ankle boots to toughen up a girly look, bring a little edge to your business attire, or make an evening look daytime friendly.

By following these four simple tips, you can double or even triple the number of outfits you can wear with your favorite ankle boots and make great use of the clothes you already own.

Thanks for reading,


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