Every September, I find myself counting down the days until I can pull my boots out of my closet. Since I wear them often starting later in the fall and through the winter months, especially when we’re in NYC, versatility is key. I usually gravitate toward classic, simple silhouettes in shades of gray, beige, brown, or black. I’ve found that a great pair of high-quality boots (especially in leather or suede) prove worth the investment time and time again, since they tend to hold up best long-term. I’m already excited to pair some of my long-time favorites, like my Joie and Margaux boots, with new fall outfits and Gal Meets Glam Collection styles.

Styling boots usually starts with what I’m wearing. For pants, I prefer pairing them with short booties. I love the way booties look with skinny jeans (like here and here), but I’ve also paired them with wide-leg cropped pants (shown here) for a completely different look. To create an especially elegant, flattering effect, pair pants and booties in similar colors to create a monochromatic look—you can see how I’ve done so in the past here and here.

I reach for knee-high or over-the-knee boots most often when I’m wearing dresses or skirts. Regardless of the length of my skirt, tall boots double as a perfect extra layer on chilly days—it’s one of the best tricks I’ve found to extend dress-wearing season well into winter. With mini-length hems, I usually wear boots with bare legs to show just a little bit of skin. As the weather gets colder, I’ll pair black tights with black boots, or opt for any of my favorite tall boots under a midi or maxi dress.

Chelsea Boots

When taking a trip during the fall, like our trip to Watch Hill last year, this pair from Sezane is typically the first pair of shoes I pack. They’re comfortable enough to walk around in all day, yet polished enough for my favorite fall outfits. I love to pair these with my favorite jeans and a cozy sweater.

Heeled Knee-High Boots

When I want a little lift, I prefer chunky heeled boots over stilettos, since I find them more comfortable and versatile. These leather knee-high boots from Loeffler Randall are the perfect shape and color to pair with my fall dresses, both mini and maxi!

Suede Bootie

There is something so classic about a simple suede bootie. These Joie booties pair effortlessly with pants and a blazer, as seen here, or underneath a Gal Meets Glam Collection maxi dress.