Anna Wintour & Co. Rep the Fashion Family in Style

When it comes to tastemakers and trendsetters in the world of fashion, the conversation typically centers on the celebrities, models, style bloggers, and other famous, fashionable faces who steal the spotlight at swanky soirees, annual awards shows, and other red-carpet events at every turn. That’s just one of the many reasons we all tend to forget that the ladies and gents behind the scenes of the fashion industry are just as fashionable and ahead of the curve — if not more so — as these well-known style stars.

But when some of fashion’s heavy hitters — including Vogue editor in chief Anna Wintour and J.Crew creative director Jenna Lyons, among others — gathered this week at The Hollywood Reporter’s annual 35 Most Powerful People in Media Celebration, it served as a quick and always-appreciated reminder of just how effortlessly chic and stylish these fashion folks are and always have been.

Wintour, who is undeniably one of the most powerful figures in both media and the fashion industry, showed up to the event in her typical polished and classic sense of style. Donning a short-sleeved, fit-and-flare dress in a bold shade of red; pointy-toed, metallic kitten heels; a double-strand crystal necklace; and her signature bob and dark sunglasses, the media maven commanded attention in the subtle-but-powerful way she always does.

Looking like she stepped right out of a J.Crew catalogue, Lyons attended the media event sporting a simple white blouse; distressed, cropped denim; and a tailored black overcoat. Pairing the look with a multi-strand chain necklace, a wrist full of bangles, t-strap heels, and her signature nerdy-chic glasses, the fashion pro looked casual and cool in her laid-back ensemble.

Supermodel Karolina Kurkova hit the event in a timeless style, opting for a flowing and belted Tamara Mellon jumpsuit, which she complemented with ankle-strap sandals, a shiny clutch, classic red lips, and beachy waves to add a bit of casual glam.

Stacey Bendet, designer of ready-to-wear brand Alice + Olivia, stuck to her failsafe dark glamour, pairing a simplistic black maxi with exaggerated eyes, a fun headpiece, and a patterned mini bag.

Designer and Project Runway judge Zac Posen also made an appearance at The Hollywood Reporter–hosted event, looking downright dapper in his charcoal trousers, tailored blazer, lightweight button down, and layered gray turtleneck.

Whether they're dressing down in denim, looking daring and vampy in an all-black ensemble, or rocking a classic red dress, Wintour, Lyons, and co. proved yet again that they can go head-to-head with even the most stylish of stars and fashion It girls. Was there ever any doubt?