Slideshow will continue in seconds. Click to skip
Olivia Palermo
Olivia's retro-cool gray booties are a perfect match for her vintage-looking shift.
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.
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.
Straight from the '40s and utterly ladylike.
Such a cool take on a traditional desert boot.
A combat style that offers just the right amount of tough.
This dusty navy pair is a great way to veer from basic black without going out of your comfort zone.
A modern take on a military style, done in a completely original pale olive.
This sand-colored option is perfect with relaxed, cuffed jeans and a cozy sweater.
Quirky and artful, but still appropriate for work.
These are the hiking boot's dressier cousin!
If heels were allowed on bowling lanes, you could bet we'd be wearing these.