Truly Stylish People Always Wear These Elite Skirt-and-Boot Pairings

It’s official: we’ve entered that time of year when the weather makes the prospect of getting dressed in the morning tumultuous. It’s far too warm to wear our warm thermal pants, yet we can’t get away with slipping into a pair of sandals either. That’s not to say that there aren’t benefits to being in the midst of transitioning from one season to the next—we get to think about what new trends we want to adopt and even shop for new staples. Still, none of that negates how challenging the prospect of picking can be when temperatures constantly fluctuate. It’s not a walk in the park, ok! However, there is an effortless formula that fashion people rely upon to make the process a bit easier: pairing skirts with boots. 

When it comes to crafting an outfit that works for transitional weather, there’s no more elite pairing than this bottom with these shoes. On a practical level, it allows one to get more usage out of both items and transition their items from winter to spring and even summer to fall. But how exactly do you style a skirt with boots easily? In an effort to help you find that answer, we first identified the four most popular shoe silhouettes based on standard heights (e.g., everything from ankle to knee-high lengths). Then, we broke down various ways to style each type of boot with different kinds of skirts. The result is a masterclass in how to pull off pairing skirts with boots, no matter the season.

1. Knee-High Boots

What You'll Need: Knee-high boots + maxi column skirt

Style notes: Don't think you can wear knee-high boots to work? Think again. Try styling the footwear with a tailored maxi skirt, turtleneck, and blazer for an office-friendly ensemble.

What You'll Need: Knee-high boots + denim slit skirt

Style notes: If you love the idea of wearing a longer skirt but still want your boots to be semi-visible, then opt for a denim skirt with a leg slit. It's the easiest way to show off your boots without having your bare legs out.

What You'll Need: Knee-high heel boots + mini skirt

Style notes: Do you prefer to show off your favorite pair of knee-high boots? Try pairing them with a mini skirt, sweater, and trench coat. It will allow your shoes to be the focal point while being functional enough for transitional weather.

What You'll Need: Knee-high western boots + bubble mini skirt

Style notes: For a more casual (but still cool) approach to styling this footwear, pair western-inspired knee-high boots with a bubble mini skirt and a t-shirt layered over a long-sleeved shirt.

What You'll Need: Knee-high riding boots + mini skirt

Style notes: For a more formal approach to styling this footwear, pair riding boots with a mini skirt, waistcoat, and longline coat.

2. Ankle Boots

What You'll Need: Slip skirt + heeled ankle boots

Style notes: One of the easiest ways to style this staple boot silhouette is by pairing it with other foundational wardrobe items. No matter the weather or what's on your calendar, you can't go wrong with styling heeled ankle boots with a long slip skirt, crewneck top, and blazer—it's a winning formula every single time.

What You'll Need: Heeled ankle boots + maxi skirt

Style Notes: While most might think that ankle boots are easy to pair with pants, the truth is that they look far chicer with skirts—case in point: the outfit above. A pair of statement ankle booties can give a basic maxi skirt and t-shirt a stylish twist.

What You'll Need: Sock ankle boots + full skirt

Style Notes: For the tightly-fitted sock boot styles, try to play with portions by pairing the footwear with a full skirt, as the contrast will allow both pieces to shine. Just be sure to keep the rest of the look minimal by wearing a crewneck sweater and a low-key handbag.

What You'll Need: Pleated midi skirt + combat ankle boots

Style Notes: Can't be bothered with wearing a pair of heeled booties? We get it. Go for a more effortlessly cool outfit for the day by pairing a pleated midi skirt with combat boots and a jumper.

What You'll Need: Maxi pencil skirt + combat boots

Style Notes: Those combat ankle boots in the back of your closet can feel more polished by recreating the outfit above. Style this footwear with a maxi pencil skirt, waistcoat, and blazer for a business casual ensemble that's far from boring.

3. Over-The-Knee Boots

What You'll Need: Over-the-knee heel Boots + leather mini skirt

Style Notes: Let's be real, over-the-knee boots are possibly one of the most challenging types of shoes to style. But what if we told you they didn't have to be? One of the easiest ways to style them is with a cute leather mini skirt with a matching leather jacket.

What You'll Need: Over-the-knee heeled boots + leather midi skirt

Style Notes: Consider this your reminder that you don't have to save these boots for more casual occasions. Make them wearable for everyday life by styling them underneath a leather midi skirt with a matching bomber jacket. It will make the sultry but a bit more approachable, plus it will keep you super warm on extra chilly days.

What You'll Need: Over-the-knee heeled boots + pleated midi skirt 

Style Notes: Instead of trying to make this boot conform to more modest approaches to dressing, you can lean into the style's innate edginess. Try paining over-the-knee boots with a plaid pleated midi skirt and fitted denim jacket to channel your inner rebel.

What You'll Need: Over-the-knee heeled boots + pencil skirt

Style Notes: Not a risktaker? That's totally ok. Rather than trying too hard when styling these boots, you can keep it simple by pairing them with a classic pencil skirt and sweater. It's a fail-proof formula.

What You'll Need: Over-the-knee heeled boots + utility skirt

Style Notes: There's a large misconception that over-the-knee boots aren't necessarily the type of footwear that can be worn daily because of how hard they are to style. But let the outfit above be your blueprint for breaking that idea. You can absolutely make this footwear feel more functional by styling it with a utility skirt, button-down shirt, and classic quilted handbag.

4. Mid-Calf Boots

What You'll Need: Lace skirt + mid-calf moto boots

Style Notes: We've all dealt with those types of boots in which their mid-calf height makes them virtually impossible to wear with jeans. But what if we told you that you didn't need pants? Enter skirts into the chat. Pairing moto boots with a lace skirt and jacket is a no-frills way to style this boot silhouette.

What You'll Need: Mid-calf cowboy boots + denim slit skirt

Style Notes: If you can't get over the idea of ditching denim altogether, then you'll want to look to the outfit above as inspiration. You might not want to wear jeans with mid-calf cowboy boots, but a denim slit skirt and statement coat is a dashing alternative.

What You'll Need: Mid-calf Chelsea boots + mini skirt

Style notes: Another effortless way to wear this boot height is by pairing it with a matching skirt suit set. Chelsea boots are already quite chic, but they can be even better when worn with a pleated mini skirt, matching blazer, sweater, and shoulder bag.

What You'll Need: Mid-calf moto boots + knit midi skirt

Style notes: Not to sound like a broken record, but matching skirt sets really are the easiest way to style boots. The prime example of this is the look above—moto boots become easy to pull off when paired with a knit midi skirt, matching crop top, and leather bomber jacket.

What You'll Need: Mid-calf heeled boots + sequin skirt

Style notes: By now, we've hopefully given you ample inspiration on how to wear skirts with boots, but should you need one last nugget of wisdom, let it be the following: it's all about choosing which piece you want to shine. You can do that quite literally by pairing taller ankle boots with a sequin skirt and a leather jacket for a night out. Or you can do that by simply choosing which item you want to be the focal point of the outfit (i.e., the skirt of the boots) and then going from there.