The Best Skirt & Boot Pairings To Try This Fall!

Isaura M. League

business casual outfit

Fall is almost round the corner, and for what we know of fall is the mix of hot cappuccino and cool breezes just makes it more warmer. As a season which is loved for Halloween, Thanksgiving and an ode to the upcoming festivities, it is also the best weather to dress up as casually as possible. No gusting winds, no cold feet. This the season to style all those flowy skirts with boots to crumple the leaves beneath it, with the pleased presence of a fabric that is comforting and snug. 

Leather Midis

For the ones who like it bold, a black leather skirt is all you need to amplify your look. Heeled boots work well with the ‘leather on leather’ aesthetic, and when contrasted with a softer, more inviting fabric such as sheer laces or chunky knits, the ensemble creates a perfect balance. 

Go with a figure-hugging skirt if you love the corporate look, or if you are the type to follow the current trends and fashion statements, opt for a more flowy silhouette which has yards of fabric to drape around you. 

Sequined Wonder

Sequins are on the rise since the pandemic ended, and we are all in awe of the new ways designers have been using the glittery reflections in their garments, and what better way to create the perfect balance between a party-worthy, scintillating beauty than with a pair of basic block boots, right?

Experiment with Vibrant Prints

A granny square knitted into an asymmetrical skirt? Take this DIY project and give it a stylish twist by pairing it with a boot that matches at least one of the colors in your skirt. 

Distressed Denim

Denim on denim is the best look to opt in fall. Denim as a material keeps you warm and stylish, making it a perfect choice to stand out amongst the falling orange leaves. Traditional denims are often in the shades of light blues, and the tint of whites match well with a white knee-high boot.

Mini Skirts FTW

Fall is by far the only season where it is the tolerable amount of cold, somewhat pleasant, and more so wholesome. Pair a mini with your knee-high boots this season for the perfect popular girl look. The versatility of this look also makes it easy to pair with a comfy oversized sweater or a fitted turtleneck for a sophisticated, clean girl aesthetic. We suggest going with a small sling bag to carry all your essentials with this look, instead of a bulky one to keep everything snug to your body, just like the fitted silhouette of the mini skirt and boots. 

Uniform it Up

A beige skirt can go a long way if you style it right. Pair the basics with an upbeat leather boot to go for a chic look for the evenings, such as a Miu Miu skirt with a basic cropped tee. Layer it with a trench coat for a rather windy day, and you will be ready to slay. 

Another way to incorporate a skirt and boot combo in your business casual looks is by layering it with a well-fitting blazer. Accessorize the basic look with a tote bag and black sunglasses for a sleek, no-nonsense silhouette. 

Maxi Dress & Boots

If skirts are not your first choice of clothing, opt for a maxi or a midi dress to match with your boots. Not only does this silhouette add the extra length to your figure (which especially counts if you are on the petite side of body frames), but also helps coordinate and juxtapose the flowy, feminine nature of a dress with the brave and daring appeal of a structured boot. 

We suggest going with a dress that has a slit, or perhaps has buttons all the way to the hemline for you to adjust the slt to your comfort, so that the boot gets its deserved show. Alternatively, you can also use the same layering trick with an oversized shirt over a dress. 

Fur Love

Fall is a humble season, but that does not mean that you can’t amp up that extra oomph in tour outfit. Pair a statement fur coat or shawl with your midi skirt to call out the bougie in you. Completing this ensemble is only possible with a leather boot to keep everything polished and poised. 

While fur will look best on any skirt that is below the knee, you can also try and pair it with a mini skirt to see if you feel confident in it. We don’t want you to go too out there, but a mini paired with a blazer and a fur shawl sure does give a chic appeal. An ultra-feminine and cute look can also be created with a fur boot itself!

A Statement Red

We know the trouble of having a wardrobe that is similar to a grayscale movie. If you are inclined towards wearing darker colors during fall, keep your accessories and additionals (such as jewelry) in a color that pops. Not only will this give a contrast to your outfit, but also colorblock it seamlessly, allowing you to utilize a statement boot with multiple outfits

Pair a plaid skirt and blazer set with red boots to drift away from the schoolgirl academia aesthetic to give a more outgoing, party or an evening supper look.

The Perfect Sole-Mate

If you don’t have a boot to style with and are looking to invest in one, go bold and beautiful with a sole that speaks volumes, truly! Platform heels have been all the rage during the Spring-Summer section of the year, and the trend is not going to turn into a fad anytime soon. If you enjoy the look of towering platforms, go with a sole that amps up every look you pair with it. 

colored sole boots
via callwehappiness

Rusty colors are a good choice to go cohesive with the season, but lavenders, pinks and reds are also a good choice if you have some pieces to match with it. 

Frequently Asked Questions

Do boots go with long skirts?

Absolutely yes! In fact, the long skirt and boot was a major trend seen as one of the street styles of NYFW. Style a flowy skirt with a structured, stiff boot and the materials of both the pieces compliment each other in the most fashionable way. 

Which colors go well with a pair of brown boots?

Brown is the color of fall! An humble, earthy tone, browns and tans work well with similar hues found in nature. Think greens, ochres and even mustard yellows to pair with this versatile shoe! Browns also work great to create an academia aesthetic for your wardrobe, so if you are naturally drawn to earthy tones, you are one step ahead to curate a cohesive wardrobe. 

Which other bottom wear can I wear with boots?

Jeans of all types (both skinny and flared) look great with boots. It is one of those combinations in which you don’t need to overthink it, and it will look effortless on all body types. 

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