September 6

New Fall Boots

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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.

fall boots
fall boots

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.

fall boots

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.

fall boots
fall boots

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.

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