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Minidresses and Boots

This '60s-inspired silhouette needs to be matched with something harder-edged to keep it from feeling too cutely retro.

Wool "Tab" dress, $414, Milly New York, tobi.com

These are tough but really simple, so they won't overwhelm the dress.

Leather "Engineer 12R" boots, $198, The Frye Company, fryeboots.com

Such a pretty, feminine style: It begs to be given a shot of sex appeal.

Silk/cotton dress, $328, Rebecca Taylor, pinkmascara.com

With a just-high-enough heel and a modern, to-the-ankle shape, these have a sultry, rocker-ish quality.

Leather "Aplegate" boots, $129.95, stevemadden.com

Slouchy and a bit oversize, this piece requires sleek, polished boots to balance its casual mood.

Wool sweater dress, $568, Vanessa Bruno, shopbop.com

These are nicely fitted and super-slick, with a sliver of a wedge to give a subtle dose of height.

Patent leather "Matilde" boots, $695, Loeffler Randall, shopbop.com

This flowy satin number is so girly: Fitted boots will offset its flowiness, and earthy ones will temper its sweetness.

Viscose/cotton dress, $375, Mint Jodi Arnold, jodiarnoldnyc.com

Small strappy buckles up the leg give this perfectly snug pair a low-key, slightly rugged feel.

Leather "Latchh" boots, $139.95, stevemadden.com