Looking for a fresh way to wear a midi skirt with boots? Think dark pleats with red boots, little floral prints or a full olive skirt with a cropped jacket.
There’s plenty to choose from here, whether you like simple outfits or something with a little more detail.
You can keep the colors neutral or go all out with sparkle.
Skirt and boot combinations worth saving
checked blazer and dark skirt
This blazer may just be one of my favorite pieces here. I love the tiny checks over the black top and long dark skirt.
Add a black belt with a curved gold-tone buckle to try the same look. The dark square-toe boots and deep brown bag finish it off without adding bright colors.
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all black and chunky soles
Don’t want to mix lots of colors? No problem!
Try this black ribbed top with a slightly shiny A-line skirt and chunky black boots. The little shoulder bag and oversized sunglasses are all the extras this outfit needs.
tiny flowers and full sleeves
How pretty is this floral skirt? The little orange and brown flowers look so good with the plain black sweater. I especially love those full sleeves.
Dark tights show through the skirt’s slit above brown heeled boots. Keep those details if you want to recreate this combination.
diagonal checks and tall boots
I love this checked skirt with the short-sleeve black turtleneck. The gray and dark diagonal checks are pretty enough on their own, so there’s no need to add another print.
Tall black boots and a small shoulder bag keep the rest simple.
matching brown and pointed boots
If you’re looking for an outfit that keeps the colors simple, go with this matching brown top and skirt. Both have fine vertical ribbing, with the long top opening below its front fastening.
The pointed black boots and bold pendant necklace are the details I’d keep.
leopard print and lace-ups
The print fans are going to love this! A leopard skirt with a ruffled lower edge sits below a black top and biker-style jacket.
Pair yours with chunky lace-up boots to follow this look. I love how the uneven hem leaves the boots on show.
brown skirt and khaki jacket
This is a lovely way to mix different shades of brown. The A-line skirt has fine vertical ridges, while the tall dark boots have little straps near the ankles.
Try a white cropped top under an open khaki jacket for the same combination. A black shoulder bag works here too.
olive cargo pockets
Don’t want a floral skirt or lots of pleats? No problem there!
Try this straight olive cargo skirt with a fitted black turtleneck and lace-up boots.
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The large flap pockets give you plenty of detail already. I’d keep the black belt and crossbody bag just like this.
wide pleats and a square buckle
I love the wide pleats on this dark skirt and the little gold-tone buckle at the waist. The loose turtleneck is tucked slightly at the front so you can see the belt.
This photo shows tights without boots, so it’s a starting point rather than a finished boot outfit. I’d add black knee-high boots to try it.
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brown front slit and black top
This is another pretty brown skirt look, but it’s a little different from the one above. The straight skirt has a front slit with brown square-toe boots underneath.
Tuck in a black ribbed turtleneck and add a dark belt if you want to recreate it. The silver-tone buckle is a nice finishing touch.
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tied blue shirt and cream skirt
This is actually one of my favorite color combinations here. The dark blue button-front shirt looks so pretty over the full cream skirt, with pointed brown boots below.
Try tying your shirt at the waist rather than tucking it in. Roll the sleeves to show the lighter cuffs, just like this.
navy sweatshirt and sheer pattern
Want to try something a little different? This navy sweatshirt sits over a long white tee and a sheer cream patterned skirt.
I love the unexpected mix with the black boots.
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The hem hangs lower on one side. Keep that uneven shape if you’re looking for a similar skirt.
checked skirt and buttoned vest
How cute is this checked skirt outfit? A taupe vest goes over a white collared shirt, with the sleeves pushed up.
The brown cap and tan ankle boots are such a pretty pairing. Try those accessories if you want to take a simple shirt-and-skirt outfit in this direction.
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striped shirt and black skirt
If you are looking for a simple outfit with a little pattern, this one is for you. The shirt has narrow vertical stripes with horizontal stripes across the chest pocket.
Tuck yours into a black skirt and add a black belt. Dark tights and heeled ankle boots complete the combination.
brown fringe and a bold belt
If you love a statement belt, then this one is for you. The wide brown belt has silver-tone decorations and a turquoise-colored center over a blue button-front shirt.
I love the long fringe along the brown skirt’s hem. Keep the pointed brown boots if you want to try this western-inspired look.
polka dots and tall brown boots
Last but definitely not least, we have this cute polka-dot skirt outfit. I love the black dots against the pale skirt, especially with that little ruffled edge.
Pair a white tee with a short brown jacket to follow this look. The tall brown boots and brown shoulder bag tie it together.