When the weather drops, we must admit our worn-in Levi’s and motorcycle boots get tons of mileage. This no fuss approach to fall dressing make them a no brainer and a classic go-to.

Inevitably, as the months drag on, we start itching for something other than this tried-and-true pairing.

We’ve rounded up some of our favorite boots that are bound to be in heavy rotation come winter.

But instead of reaching for your 501’s, opt for skirts, a warm, chunky knit and opaque tights to get you out of a style rut.


Perfect for an edgy, downtown vibe, Iro’s Jalie Skirt is anything but basic. Pair it with Maison Martin Margiela’s tilted boots for a luxe minimalist effect. Ann Demeulemeester’s cuff provides a great contrast to Johnny’s slouchy sweater to round out this sleek, polished look.


Suno’s embroidered skirt paired with Guess’ Finlay booties give a fresh update to this look inspired by the wild west. Channel your inner “Little House on the Prairie” vibes by topping off this look with a Rag & Bone fedora.


Thankfully, in fashion everything is cyclical. Thanks to Saint Laurent’s Hedi Slimane, 90s fashion has definitely made a comeback, and we can’t get enough. Update old favorites by opting for richer textures and neutral colors. River Island’s skater skirt pops, when paired with leather over-the-knee boots and Alexander Wang’s sleek Oyster backpack.


You’ll be party ready when pairing Marios Schwab’s sequined pencil skirt with Shoe Republic’s peep toe booties. Little else is needed in terms of accessories for this ultra feminine look. We just couldn’t resist upping the glam factor by adding Elizabeth and James’ shearling bag to round out this look.


Pair Saint Laurent’s studded moto boots with a color block skirt for a bold, edgy look. A heavy metal cuff by Reed Krakoff offsets a feminine ear cuff and provides a nice compliment to the heavy boots.