How to wear ankle boots for a professional image

While ankle boots (a.k.a. booties) are not a completely new trend, they’re hotter than ever this year. But it seems many women see booties as trendy and less professional. To the former, they’ve certainly been around long enough to show they’re fashionable, but not trendy. To the latter, ankle boots with skirts may not be the way to go if you work in an extremely conservative office, but they’re a great updated and stylish option for casual and business casual environments.

Here are a few different ways to wear ankle boots to refresh your wardrobe:

Wearing an ankle boot with wide legged trousers provides warmth without all of the bulk of a tall boot. Granted you don’t see all of the “cuteness” of the boot, but I’m sure this is music to your ears if you have a hard time finding tall boots to fit your calves. If you’d like to wear your booties this way, aim for a pair with a pointed or tapered toe. You’ll look sleek, and your legs will look a mile long! (Elongating your body is a great non-verbal way of adding stature, i.e. power to your look.)



Teaming cropped pants with a taller shaft ankle boot is a great way to get more mileage out of said pants for fall and warmer winter days. If your pants are close to or a little over the top of the boot, you still get the look with more warmth than cropped pants with flats sans socks.  For skinny jeans, you want to roll them to create just a sliver of skin between your boots and jeans. (No tucking, please.) And while it’s not totally main stream, and I don’t necessarily recommend it, it probably wouldn’t be then end of the world if you wore the look with dark opaque tights/socks.

Skirts and boots go together like bread and butter, but for ages the look has been tall boots with skirts. You probably have plenty of knee length and midi skirts, so why not mix things up a bit and pair them with booties? Just yesterday when I was creating outfits with one of my premium clients, who works in a real estate office, she donned a printed, somewhat classic, sweater dress. The outfit looked great with tall black boots, but was elevated to FABULOUS when we paired it with gray tights and gray booties!

Skirt with booties

Pop on over to my Pinterest page for tons more examples of booties with skirts and cropped pants/jeans. You don’t have to have an account to take a peek, but if you have one, I’d love for you to follow me while you’re there!

While it’s not a hard, fast rule these days, matching your tights and boots will lengthen your legs the best. Skipping tights? Choose boots to match your hem or flatter your skin tone. FYI, going without tights is a more informal look that I don’t always advise…there are a lot of factors that play into your decision.

I especially love midi skirts with flat, ankle boots. It’s a great way to dress down your skirt and pamper your feet at the same time. One of my favorite fall outfits has been a long, tube skirt with a knit top and my Sam Edelman booties. Because my boots are a little rugged looking, I harmonize the look by wearing chunky, rugged looking jewelry. And in flats, my feet love me!

Whether you prefer your booties with trousers, jeans, leggings or you’re all in with ankle boots and a skirt, adding this style into your wardrobe is a great way to update even classic pieces and keep your wardrobe fresh! I’d love to know how you like to wear your booties or if you have any questions, so feel free to leave a comment below.

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