Like peanut butter and jelly, Thelma and Louise or Ina Garten and fresh organic ingredients (or store bought is fine), some things are just better when they’re together. And the same goes for a fall dress and boots. Here, we break down the eight greatest no-fail ways to pair dresses and skirts with boots for your most fashionable fall yet.
8 Fall Dress and Boot Combos to Wear on Repeat All Season Long
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Published Oct 26, 2018
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1. Miniskirt + Flat Chelsea Boots
One of the best fashion tips we’ve ever heard: The shorter the hemline, the lower the heel. A tough flat bootie is the perfect way to balance out a sexy mini-length dress or skirt.
Get the look: Forever 21 skirt ($18); Blank NYC skirt ($98); Blondo boots ($150); Marc Fisher LTD. boots ($180)
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2. Flouncy Pleats + Slim-fit Otk Boots
Who needs tights when you can rock cozy suede boots instead? A leg-hugging over-the-knee pair helps keep your proportions in check while you twirl your heart out walk along in a full, pleated skirt.
Get the look: Abercrombie & Fitch skirt ($58); Eloquii skirt ($100); Sam Edelman boots ($225); Alias Mae boots ($400)
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3. A-line + Structured Tall Boot
A shapely skirt and stiff leather boots might seem like a lot of material, but the combo is actually chicly elevated and totally put-together.
Get the look: Lane Bryant dress ($90); J.Crew dress ($118); Sarto by Franco Sarto boots ($140); M.Gemi boots ($548)
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4. Flowy Midi + Sock Boots
Volume control is key when wearing a longer billowy silhouette. Luckily, the tight sock boot trend is still going strong. Choose a pair that hits a bit higher than your dress’s hemline for maximum leg slimming and lengthening effect.
Get the look: Leith boots ($110); Nic + Zoe skirt ($188); Schutz boots ($290); Vince skirt ($325)
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5. Hip-hugging Knee-length + Slouchy Boots
The slouched ’80s style is back, but please don’t go wearing it with your acid wash jeans. Instead, try a simple unfussy dress that hugs your curves in all the right places.
Get the look: Bar III dress ($90); Sole Society boots ($120); Nine West boots ($144); Eliza J dress ($158)
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6. Maxi Dress + White Booties
Don’t let yourself get buried under a long hemline. A pop of stark white boots under a floor-grazing dress adds lightness and brightness.
Get the look: Halogen boots ($120); Betsey Johnson dress ($124); Splendid boots ($199); Equipment dress ($498); Oscar de la Renta dress ($2,490)
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7. Pencil Skirt + Tall Stilettos
A fitted pencil skirt is wonderful for lengthening your frame, so why not continue that effect with some boots that do the same? Look for a pair that fits close to your leg (in other words, opt for a sock-like fit over slouched leather) and that will overlap just two or three inches with the hem of your skirt.
Get the look: Halogen x Atlantic-Pacific skirt ($89); Boden skirt ($110); Calvin Klein boots ($229); Linea Palo boots ($260)
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8. Midi Skirt + Pointy-toe Booties
To avoid looking frumpy in a style beloved by both the Amish and the fashion set, select boots with a sleek pointed toe and a heel that’s at least two inches high. Even better if you can show a little shin between the top of your boots and the bottom of your skirt (how scandalous!).
Get the look: Topshop skirt ($85); Banana Republic skirt ($118); Karl Lagerfeld Paris boots ($149); M.Gemi boots ($398)
