4 Fresh Takes on Classic Boots I'm Buying Right Now

Kristen Nichols, Who What Wear’s managing editor, is a staunch advocate of high-waist vintage denim, classic footwear, and cropped tweed jackets, and you better believe she only adds trends to her outfit as she sees fit. "I see my style as ever-evolving, and I’m not afraid to embrace new trends, but if I’m making a big investment, I choose classic pieces over items that only have a one-season shelf life,” she explains.

Given that Kristen and I both work in Who What Wear’s Los Angeles office, I have the daily pleasure of seeing all of the polished looks she puts together, and I’m constantly taking notes. Currently on her radar? The fall boot lineup from PAIGE. Personally, I’ve been following the brand’s shoe evolution since they launched, and I was thrilled to hear that Kristen was eyeing them too. She showed me her top four favorites, how she’s styling them, and offered some nuggets of styling wisdom.

Stiletto Thigh-High Boots

Pants? Boots? Boots that look like pants? Whatever you want to call it, we’ll take it. "I took inspiration from one of Carolyn Bessette-Kennedy’s iconic ’90s looks that paired a black V-neck sweater with a midi skirt and over-the-knee boots,” Kristen told me when I asked her about the genesis of this ensemble. At first glance, a stiletto boot can be a little intimidating, but when styled in a classic way, it’s actually super easy to pull off. It really comes down to finding the right proportions, Kristen says: "I find it’s always pretty foolproof to layer them under a slip skirt that falls below the knees.”

Lace-Up Boots

Let’s take a moment to appreciate this outfit: It’s part pink, part chocolate-brown, and there’s a chunky gold necklace involved. In theory, this is simply a sweater-and–skinny jeans outfit. Not rocket science, right? But it’s Kristen’s thoughtful details that turn it up a notch. "Sticking to one color family always reads as elevated, which is why I chose to pair these chocolate jeans with brown boots, as opposed to black,” she notes. And hey, if black is your thing, you’re in luck.

Ankle Boots

Ah, the classic ankle boot: It’s basically the LBD of footwear. Kristen noted that a black suede boot is particularly essential to help mix up the textures when you’re leaning into leather: "All-leather looks will be one of the biggest trends this fall—and it happens to be one I’m most excited to incorporate into my wardrobe this season. To pull it off, I love the idea of mixing leather in different colors, like the cream and black paired here.”

Over-The-Knee Boots

An over-the-knee flat boot is an absolute staple in Kristin’s wardrobe. It also happens to be the perfect footwear to style skinny jeans with. Why? It creates a sleek line, making it an ultra-flattering style to wear if you want a streamlined effect (or if you’re feeling just a little equestrian). Kristen noted that balance between the boot and the printed jacket is what makes this look feel elevated: "Skinny jeans and over-the-knee boots were spotted all over the fall 2019 runways, so they were my starting point for this outfit. This toile jacket in a luxe jacquard is the perfect statement piece to add dimension to the look.” Note PAIGE's silver touch on the heel again? Subtle, sure, but also chic AF.