Rich-Looking Ski Outfits Inspired by Princess Diana and Jackie Kennedy

A ski trip is as much about careening down a mountainside as it is the perfect opportunity to embrace winter dressing in all its forms. After all, layering is an art that invites both practicality and ingenuity. From heritage-rich Fair Isle sweaters to one of the latest hat trends, ski wear offers the chance to play with a seamless pairing of high-performance gear with loud luxury fashion. Plus, ski style remains delightfully frozen in time, still harkening back to the same inspiration from Princess Diana in St. Moritz, Jackie Kennedy in Aspen, and Audrey Hepburn enjoying a ski break on the piste (with wine and fondue obviously). Of course, your winter jacket and thermal base layers are non-negotiable—we're not suggesting you forgo the necessary armor. But consider your next alpine excursion an invitation to experiment, especially off the slopes: Pair your snowproof pants with a furry Ugg, or offset that perfectly engineered parka with your new Bottega bag. The interplay of old and new, a bit practical and indulgent, makes slope-side style so much fun to recreate.

Start with a Sweater

Heritage-inspired ski sweaters in classic Fair Isle motifs—favorites of both royals and A-listers—and timeless cable knit weaves are must-pack staples for any slope-side trip. Off the mountain, you can elevate your après-ski look with tailored trousers and luxe fabrics like velvet and sequins that add depth and play with texture. Meanwhile, classic layers in cashmere and wool are always a good choice for water-wicking and warmth.

Play with a Personality Puffer

Keeping the cold away doesn’t have to mean sacrificing your personal style. A puffer jacket in a trending hue, a poppy print, or a geometric pattern can do everything—keeping you well-equipped on the mountain and in an aprés ski setting. Start with a water-resistant base layer for practicality, then layer on sleek ski pants and cozy, textured snow boots to keep the chill at bay.

Add Winter-Proof Accessories

Winter’s chill calls for cozy accessories that keep you warm and elevate your cold-weather wardrobe. Consider your outfit's winter essentials, functional necessities, and finishing touches. From charm-clad beanies to classic cashmere scarves, these pieces can actually become the standout heroes of your ski ensemble or everyday winter outfit. On super cold days, balaclavas and knit hoods offer extra insulation, while a colorful crochet version can inject a playful pop of color.

Style Some Statement Snow Pants

This season, finding snow-proof pants and bibbs that blend style and practicality is easier than ever as they take their design cues from winter’s biggest fashion and color trends. High-waisted silhouettes, retro '70s motifs, and utility-inspired designs reflect fashion’s enduring love for combining all-terrain ski wear with luxury.

Cozy Up in Base Layers

Thermal undergarments are as essential as outerwear when planning the perfect ski vacation look. Fleece-lined leggings offer unbeatable warmth in freezing temperatures while artfully sandwiching your sleek merino wool turtlenecks and sweaters, provides a breathable, moisture-wicking foundation for layering.

Lean Into Après-Ski

Let’s be honest: any adult ski trip is primarily about the après-ski experience. After all the hard work on the slopes, it’s time to embrace fun accessories—that both support your look—and enhance the glamour of après-ski. Now is the perfect opportunity to showcase the pieces you packed but couldn’t wear on the mountain. Consider indulgent fabrics like a faux fur or shearling teddy coat, which always feel right at home while enjoying a drink by the fire.