Work It! Office-Appropriate Over The Knee Boots

Olivia palermo work appropriate boots

When it comes to one of this fall/winter’s hottest trends, over-the-knee boots, there’s a fine line between appropriate and too much. In this post, our stylists guide you through the best office-friendly over-the-knee boot looks.



“Wearing all black might be tempting this time of year, but instead, go for chic neutrals like taupe and grey in suede. The other day I was with Agnes Bielska, Barney’s superstar personal shopper, and we were both dying over these Gianvito Rossi grey boots. You can’t go wrong with them” says VT co-founder Jesse Garza.

New York-based VT stylist Kellye Henton adds, “If you are going to wear black over-the-knee boots, pair them with black opaque tights and a mid-length ladylike dress. It will create a clean, sleek line and elongate your silhouette.” 

Olivia-Palermo-perfected-classics-powder skirt

Gianvito Rossi over the knee suede boots


If you want to keep it professional, stray away from pairing your over the knee boots with short skirts/dresses, shorts or leggings. Go for a midi a-line skirt (like Olivia Palermo), a modernist boxy dress (as seen in the Celine’s collection from last season), or a power lady dress (Victoria Beckham nails the look). The power lady dress will bring your look from day into evening with a switch of bag to clutch.

Celine fall 2013 over the knee bootsVictoria Beckham over the knee boots pencil dress copy


While there’s a way to wear high heel over-the-knee boots and not channel Pretty Woman, your safest and most practical bet are block heel and flat boots. “Practical, comfortable, and chic, flat over-the-knee Prada boots were Lisa Marie’s go-to while during Paris Fashion Week. A girl’s gotta be able to get around! Her fresh look drew attention of Bill Cunningham, too! Lesson? You don’t always need high heels to make a style statement.”

All in all, there’s a very fine line between tastefully sexy and over the top with over-the-knee boots, and we hope that our stylists’ guidelines will make it easy for you! Shop our favorite pairs below.