Boots are a three-season staple for most Minnesotans, keeping our feet warm and dry through the fleeting fall, long winter and wet spring. But many women struggle to find styles that work for their figures and with their wardrobes. Others wonder how to select from knee-high, mid-calf and ankle styles when assembling outfits.

Here’s a guide to making boots work for you. Let’s begin with this primer on length.

Tall boots: Knee-high boots are eternally chic, though they can be tough to fit. Ideally, the shaft should hit around one inch below the bottom of your kneecap and fit closely to your calf. Both are tough marks to hit since boots come in a variety of heights and widths, so aim for both and if you hit one consider yourself fortunate. Tall boots should taper at the ankle, too, so your leg’s true shape is revealed. Otherwise they can create the impression of much-dreaded “cankles.”

Mid-calf boots: Many mid-calf boots can be challenging to style because they hit at the widest part of the calf, visually widening the lower part of your leg. Heeding proper fit will help. They should fit closely, hugging the calf without squeezing. Styles that hang away from the leg will make the calf look wider still, so seek pairs that are snug.

Booties: Ankle boots have been around for ages, but over the past five years they’ve surpassed taller styles in popularity. This shape was once worn exclusively beneath boot-cut jeans and wide-legged slacks, but now they’re paired with everything from shorts and sundresses in summer to wool socks and leggings in winter. Picking a height that works for you is key. Booties that are short enough to reveal the curve of your ankle bone will be the easiest to style with skirts and dresses. Taller booties that hide your ankle may make your legs look stocky.

Tall and sleek

Why this works: Sleek, relatively formal boots work wonderfully with tights, and can be paired with skirts and dresses for feminine winter looks. Contrasting hosiery works here so long as the dress or skirt hemline hits at the top of the kneecap or above. You need to show the curve of the knee to showcase your leg’s true shape.

Also try: For a longer leg line, choose hosiery that is a similar color to your boots. Sleek boots can also look marvelous in casual mixes, with leggings or skinny jeans.

What to avoid: Skirts that either graze or fall below tall boot tops can often make legs appear stocky and stumpy. Showing all or most of your knee will work best.

Cole Haan Russell, $279.95, Cole Haan, Galleria,

Tall and rugged

Why this works: Casual, rugged or distressed boots look fantastic with skinny jeans. If your boots gap at the top, try adding some chunky boot socks to fill the space. Allow just a sliver of the sock to show above the boot line for optimum leg flattery.

Also try: Match them with a dress outfit with tights and a cozy scarf. Rugged boots also are fabulous with leggings and tunics, a chic weekend staple for many Minnesotan women.

What to avoid: Truly rugged boots don’t belong at the office, so don’t mix these with skirt suits or dressy separates.

Mossimo Kerryl, $39.99, Target,

Snug mid-calf boots

Why this works: The best way to keep mid-calf boots from chopping up your leg line is to wear them with like-colored tights, leggings or slim pants. With little or no color difference between boots and legs, you create a longer, leaner leg all the way down to the floor. If you don’t have hose or leggings in all of the same colors as your boots, don’t fret. Go for a similar color value instead of trying to match shades.

Also try: Textured and patterned leggings and tights in similar colors to your boots.

What to avoid: High contrast between boots and legwear will create that hard line across your calf, visually widening it.

Fiorentini + Baker Eternity, $585, Pumpz & Co, Galleria,

Dressy booties

Why this works: Since booties end at the ankle, they can cut off your leg line in an awkward way. Ease the transition with like-colored legwear. Black booties with a black patterned tight still do a great job of creating a relatively unbroken line. Add color to your outfit up top with a bright skirt or dress.

Also try: Opaque tights and leggings in similar color values will be equally flattering.

What to avoid: If you go for a skirt or dress, longer hemlines that cover the knee or hit mid-calf will make your legs seem stumpy.

Vaneli Lavi, $159. Marmi, Galleria,

Casual booties

Why this works: Cuffing your jeans to hit right where your bootie ends creates a very modern look. In summer you can show a bit of bare ankle between jean and shoe, but in winter cuff a little lower and wear cute patterned socks in case of peekage. Cuffed skinnies show the shape and curve of the calf.

Also try: Booties and cozy socks can make fun, casual pairings. Scrunch your socks so they just peek out from the bootie tops, and wear the combo with leggings or skinny jeans tucked inside.

What to avoid: Although tough booties can be mixed with dressier items, truly rugged or undeniably casual styles won’t fly at most conservative workplaces.

Mossimo Kodi, $24.48, Target,


Sally McGraw is a Minneapolis-based style blogger and author of Already Pretty (