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Olivia's retro-cool gray booties are a perfect match for her vintage-looking shift.
PROENZA SCHOULER SUEDE LACE-UP BOOTS, $795,
Photo Credit: Startraks
Equal parts Victorian and sleek, with a cute cap-toe detail.
The rich cognac color is timeless.
These really hug the ankle and give all the height you could ever want. The moto buckle is a nice edgy touch, too.
A foldover detail slims the ankle, plus the green is totally unexpected.
DIANE VON FURSTENBERG, $395,
Wing tips go feminine with a stacked heel, graceful lines, and a patent finish.
The wraparound ankle strap adds an extra shot of attitude to this colorful pair.
JEFFREY CAMPBELL, $175,
Straight from the '40s and utterly ladylike.
NINE WEST, $76.30,
Such a cool take on a traditional desert boot.
ROSEGOLD GENIE, $185,
A combat style that offers just the right amount of tough.
FOREVER 21, $27.80,
This dusty navy pair is a great way to veer from basic black without going out of your comfort zone.
ELIZABETH AND JAMES, $395,
A modern take on a military style, done in a completely original pale olive.
DOLCE VITA, $229,
This sand-colored option is perfect with relaxed, cuffed jeans and a cozy sweater.
STEVE MADDEN, $39.95,
Quirky and artful, but still appropriate for work.
PAUL SMITH, $354.20,
These are the hiking boot's dressier cousin!
If heels were allowed on bowling lanes, you could bet we'd be wearing these.