Look for: Elastic gussets, stretchy leather or fabric, buckles, or laces for extra give. Also, an angled cuff (not one that cuts straight across) creates a flattering curve on the leg.
Avoid: Pull-on styles that are hard to get into, boots that end at the widest part of the calf muscle, and wraparound straps that accentuate any fullness.
Try wearing them: With tights or leggings in a matching color to create a long, lean line.
2 of 6Jason Brownrigg
If You Have Short Legs
Look for: Heels or wedges to lengthen the legs visually. “Stick with a streamlined design with vertical accents—zippers or laces—so the eye moves upward instead of side to side,” says Meghan Cleary, a shoe expert and the author of The Perfect Fit.
Avoid: Square toes, straps, and slouchy cuts that add width.
Try wearing them: With a pencil skirt or slim pants to continue the sleek, elongating effect.
3 of 6Jason Brownrigg
If You Have Wide Feet
Look for: Round or almond-shaped (rather than pointy) toes that offer plenty of room and slim heels for a touch of femininity. “A zipper that opens to the sole is easiest to slip your feet into,” says Tousif Ghani, a store manager for Geox in New York City.
Avoid: “Broadening details, like buckles or straps, near the ball of the foot,” says shoe designer Chie Mihara. Chunky heels also look masculine.
Try wearing them: With trousers that skim the toe box, to break up the width of the foot.
4 of 6Jason Brownrigg
If You Have Skinny Calves
Look for: Anything with flexibility—buckles, laces, stretchy material—so the boots can mold to the calves, says Ghani. A slim ankle style also tends to fit well. Make legs look curvier with a bold color, like plum or gray, or three-dimensional details like a ruffle.
Avoid: Slouchy cuts. “More than an inch of space between the boot and the leg exacerbates the issue,” says Mihara.
Try wearing them: With contrasting tights and a patterned skirt to add more dimension.
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Boots: Two Annoying Problems and How to Solve Them
“My Favorite Pair Just Doesn’t Fit”
A good shoe-repair shop can make surprising alterations.
Stretch the shafts up to a half inch: $25 to $50.
Widen the shafts by adding up to three inches of extra material: $50 to $200.
Insert an elastic gusset in each boot: $40 to $120.
Take in the shafts up to six inches: $80 to $140.
Widen the toe boxes up to a half inch: $15 to $25.
Shorten the shafts: $40 to $100.
No reputable cobblers near you? NuShoe.com has a mail-order repair service.
“I Can Never Find My Size”
Do your feet fall on the small or large end of the spectrum? Bookmark these especially accommodating sites.
“I’m Worried That Rain and Snow Will Ruin My Boots”
First pretreat leather and suede styles: Spray them with a silicone-free water repellent, such as Vectra-16 Spray ($13, footwearetc.com). Reapply at least twice a season. Have a cobbler attach rubber sole protectors (about $20) to the bottoms so that water won’t seep in.
When boots get wet: Stuff them with newspaper to preserve the shape and speed the air-drying process. Next, condition leather with colorless Kiwi Leather Lotion ($7, shoetreemarketplace.com). Or remove water marks on suede or nubuck with a suede eraser, and restore the nap with a brush. (Kiwi Suede & Nubuck Kit, $7.50, shoetreemarketplace.com.)
If boots get stained with salt: Combine 1 part white vinegar and 1 part water. Using a paper towel, dab the solution onto the spots until they disappear. (Suede boots should be cleaned by a professional.)