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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, www.pumpzco.com
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, shop.marmishoes.com
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, www.target.com
Sally McGraw is a Minneapolis-based style blogger and author of Already Pretty (www.alreadypretty.com).