Kendall Jenner Makes the Case for Architectural Shirting at West Hollywood Holiday Party
Kendall Jenner descended upon the OBB Media holiday party in West Hollywood on December 13th, delivering a sartorial lesson in the enduring power of contrast dressing. The supermodel’s appearance wasn’t merely an outfit—it was a manifesto on how to wield monochrome with surgical precision and modern sensibility.
The foundation of Jenner’s look centered on a tailored black mini-skirt paired with a crisp white long-sleeved button-up shirt, a combination that might read pedestrian in less capable hands. But Jenner’s styling elevated the ensemble into something altogether more compelling. The shirt remained untucked yet disciplined, cinched at the waist with a narrow black belt—a technique that maintained structural integrity while allowing the fabric to drape naturally over her hips, creating movement without sacrificing polish.
The true genius, however, revealed itself in the details. Oversized, dramatically flared cuffs transformed the white shirt from boardroom basic to contemporary architectural statement, their exaggerated proportions adding a refined, almost sculptural element that pushed the look firmly into 2025 territory. This wasn’t your mother’s work-appropriate blouse—this was high-contrast dressing reimagined for the Instagram era.
Jenner completed the monochromatic vision with sheer black hosiery and sleek black pointed-toe stiletto pumps, creating an unbroken, elegant vertical line from hemline to floor. A black handheld clutch served as the final punctuation mark, reinforcing her unwavering commitment to the two-tone scheme with the kind of discipline that separates style icons from mere trend followers.
Her footwear choice proved particularly noteworthy—The Row’s Cybil Mules, featuring strapless short stilettos and pointy toe boxes, have become something of a signature silhouette for the model. The kitten heel style has emerged as Jenner’s go-to, photographed on her feet with stirrup leggings as recently as 2024. It’s the kind of foolproof pick that works equally well for December holiday parties and casual street style moments.
But Jenner’s dedication to The Row extended beyond footwear. She carried the brand’s coveted Dalia Bag, the geometric top-handle purse that Dakota Johnson, Zoë Kravitz, and Emily Ratajkowski collectively elevated to It-bag status months prior. Saturday’s appearance marked Jenner’s inaugural Dalia-clad outing—a calculated move that signals her understanding of fashion’s invisible hierarchies and her willingness to embrace what’s already been vetted by her industry peers.
Earlier that evening, Jenner was spotted departing another holiday engagement in black stirrup pants paired with a navy blue fitted jacket featuring brown shearling trim along the collar, closure, and cuffs—a Ladies-of-the-Eighties workwear moment accessorized with a brown handbag, thin leather-strap watch, and blood red nails. The pointed-toe kitten heels reinforced the retro-professional aesthetic, proving Jenner’s range extends far beyond a single style narrative.
While Dakota Johnson’s $11,000 leopard fur Valentino from December 11th remains the season’s most extravagant street style splurge, Jenner’s approach feels more attainable, more replicable—and perhaps, more relevant for exactly that reason.
