Sock boots may be the season’s trendiest pick and lug-soles the hero for winter’s snowiest days, but pointed-toe boots are for everything in between. The classic silhouette has been reimagined in fresh, modern ways—yet its timeless appeal remains uncontested, effortlessly carrying you through the day with sharp, polished ease.
Vogue’s Favorite Pointed-Toe Boots, at a Glance:
From supple black leather to rich brown suede and even bold chocolate pony hair, there’s a style to match every mood and outfit, giving any look a refined edge while still feeling current and endlessly versatile. Their versatility makes them the ultimate footwear investment, no matter how your wardrobe evolves. Few brands proves that point quite like The Row: After this year’s CFDA Awards—where sister duo Mary-Kate and Ashley Olsen took home the Accessories Designer of the Year award for their work with The Row—it’s little wonder to see how coveted their Liisa bootie is. With its sleek, sculpted shape and perfectly pointed toe, it delivers instant sophistication to anything you pair it with, proving why a beautifully made boot always outlasts the trends.
Styling-wise, there’s no limit to how you can wear it: Slip it beneath classic denim and a white tee for an effortlessly chic ensemble, or style a knee-high pair with a pencil skirt and statement belt for a bolder, directional look. Whether you find yourself drawn to J. Crew’s classic black ankle bootie, Tory Burch’s pierced toe bootie, or Chloé’s bohemian studs, there’s a version on the market that fits every personality and price point.
Below, discover the best pointed-toe boots to shop this season—from modern minimalist takes to embellished maximalist shapes.
The Classic Ankle Style
Boots remain one of the most versatile footwear staples, from daily wear to nights out. This winter, let the pointed bootie take center stage as your go-to choice for polished versatility. Manolo Blahnik’s stacked heel offers comfort and elegance for long days on the move, while Loeffler Randall’s Doria boots look best peeking out from beneath a statement dress.
The Knee-High Silhouette
The knee-high boot continues to define the season and makes for a great match with pencil skirts, skinny jeans, or sleek straight-leg trousers. Channel ’90s minimalism with glove-like silhouettes or embrace a touch of the countryside with equestrian and western-inspired designs.
The Trending Brown Suede
This year’s hero hue comes alive in suede—bringing warmth and depth to winter dressing. The Row’s modern take on the glove boot is best with a cozy knit dress, while Saint Laurent’s long and lean version strikes a sharper and more sculptural note that would be best contrasted against relaxed denim.
The Printed and Embellished Pairs
Designers are having fun with the classic pointed shape this season. Khaite, Chloé, Tory Burch, and Jil Sander all introduced (or brought back) decorative details—buckles, embellishments, metal piercings, or snakelike finishes—to breathe new life into the familiar shape. One revival gaining attention this season is Chloé’s Susanna buckled ankle boot. A favorite from the early 2010’s at the height of the indie sleaze movement, it’s triple buckle and gold studded flower motif fits seamlessly into today’s boho mood.
Khaite
Nevada stretch high boots
Modern Twists
For more subtle twists, brands explored new silhouettes, textures, and fabrics: Toteme’s croc-embossed sock bootie is a favorite of the season for an IYKYK statement, while Ayede’s chocolate calf-hair iteration is a great moment to incorporate materiality and allure into your look.
