How to Style These Essential Boots
Sometimes the easiest way to get dressed is to choose your boots first. The shaft height, toe shape and heel help determine which pants work, where a skirt should fall and how much volume to wear on top.
For fall, I’d build around three essential shapes: 1) a sleek ankle boot, 2) a tall riding boot, and 3) a heeled knee boot. Each creates a different mood and a different reason to revisit what’s already in your closet.
Look 1: The Sleek Ankle Boot and Full Length Denim
Choose a black or brown ankle boot with a tapered toe and a slim or sock-like shaft, then add full-length straight jeans, a fine black knit and a camel coat. Let the denim fall over the boot rather than bunch above it. A black belt and a roomy leather tote finish the look. This is the outfit I’d reach for on a busy weekday when I want everything to feel pulled together quickly.
Tara’s Style Edit: Try the jeans with the boots before hemming. The hem should clear the floor, and the boot shaft should sit smoothly underneath.
Look 2: The Heeled Knee Boot and Short Skirt
A modest, heeled knee-high boot gives a short skirt an elevated feel. I’d pair a dark brown leather version with a charcoal wool mini, opaque tights and an oatmeal sweater. Add a navy coat and a simple crossbody bag. Keep the sweater slightly relaxed and tuck just enough to show the waist; the proportions should feel comfortable rather than like a riding uniform.
Tara’s Style Edit: Try tall boots with the tights you’ll wear. The shaft should feel comfortable at the calf and behind the knee when you sit.
Look 3: The Riding Boot and Fluid Midi
For dinner, choose a chocolate suede knee boot or a solid black riding boot paired with a midi skirt in cream or a fun pattern. Add a fitted espresso knit and a cropped jacket that ends near the waist. The skirt should skim over the shaft, creating an uninterrupted line. Finish with sculptural earrings and a small clutch; the mix of suede and movement supplies the interest.
Tara’s Style Edit: Check the skirt in motion. A boot shaft that catches the fabric or pushes it outward can disrupt an otherwise beautiful silhouette. Before buying another pair, decide which outfit gap it fills. The most useful boots make several pieces you already own easier to wear.
