The Essential Guide to Styling High Knee Boots This Winter

It's amazing how fashion always comes full circle. I remember circa 2017 when riding boots were the undisputed accessory of the Fall/Winter season. They offered a perfect balance of utility and flair, instantly spicing up basic looks—a trend I wholeheartedly embraced.

Fast forward to today, and knee high boots are making their return right here in Milan. Women are effortlessly sporting both heeled and flat styles, transitioning them seamlessly across all times of the day. As we move deeper into the crisp, cooler winter months, this versatile boot is proving to be an essential anchor for any stylish wardrobe.

Here are 3 of my favorite ways to style knee high boots this upcoming season.

1. Upgrading The Everyday Classic: Jean Tuck-In

This is the most timeless way to wear knee-high boots. Whether you opt for a flat or heeled boot does not matter as much - the simple act of tucking a well-fitting pair of jeans into the shaft will automatically polish off your outfit.

Pro-Tip: For the best fit and least bunching, choose a stretch or skinny cut of denim. 

2. Winterizing Summer Garments: Long Coat and Short Combo

Think shorts are strictly reserved for summer? Think again! This is a sophisticated way to incorporate warm-weather staples into your winter wardrobe. By playing with proportions, you can expertly orchestrate a chic daytime look that will not leave you cold. The secret lies in the combination: opaque tights, a dramatic long coat, and flat knee-high boots create necessary warmth and balance.

3. Day to Night Transition: The All-Black Uniform

Want a daytime look that seamlessly transitions to night? The All-Black Uniform is the answer. This ensemble demands use of different textures and fabrics—think combining leather, satin, and wool—to add depth and visual interest to the monochromatic scheme. Pairing heeled boots with a midi skirt creates a silhouette that serves a dual purpose: it keeps you warm while making you look undeniably elegant. 

These styling suggestions are just the tip of the iceberg. There are countless other ways to leverage the knee high boot in your winter wardrobe rotation, though these are great places to start. Which look will you try out first?

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