Take a page out of the late legendary fashion editor Diana Vreeland’s book and update your look with the unexpected, like these style mavericks.

Suzanne Timmins

Standing in heels at a cocktail party can be painful. But the modern sneakers in vogue feature sparkles or jewels (see above). For a red-carpet mode, this fashion director is a master-class study on how you can cover up and still look ravishing if you opt for a figure-hugging gown in an eye-catching print.

Kirsten Owen

For an evening gala, this model who helped popularize the grunge movement of the ’90s gives a simple black dress an edgy vibe when paired with boots. The asymmetrical hem on the dress softens the punky attitude. Note the absence of heavy sparkly evening accessories; it ups the cool factor.

Jean Fleming

Optical illusions such as graphic black-and-white blocks can work wonders in off-setting or hiding any figure flaws—styling tricks of the trade for this model and personal shopper. While this dress is striking in simplicity, the one-shoulder style gives a touch of cocktail glam while dark hosiery and pumps add a certain amount of edge.

Vonna Bitove

A gold medal winner in orchestrating the right mix of simplicity with a soupçon of decadence. Shimmering pinstripes and the narrow, above-ankle length both help to elongate the figure. But she ramps up the wattage with accessories—a bold gold minaudière and sexy T-strap high-heeled sandals.

Lynda Prince

This fashion doyenne’s play with proportions is masterful: a longer jacket with cropped pants. It’s also a unique take on the cocktail pantsuit. A printed pant adds interest to an otherwise ordinary white shirt and black jacket combo. And adding a pussy bow tie—which can easily be achieved with a long narrow scarf—is a chic and elegant touch.

Simona Schnaider

Here is a shining example on how to add some vitality to a beloved classic. The hard-working LBD that has saved you on many what-to-wear dilemmas can feel uninspiring after too many outings. Give it an entirely fresh outlook by pairing with a metallic cropped bomber, which adds some youthful vigour and a contemporary feel to this look.

Hanan Shams

An all-black outfit can be chic, but this interior architect takes it one step further with a dramatic shape and an explosion of interesting detailing on the bodice, which turns this dress into a conversation piece. The embellishment is esoteric in vibe and gives an arty sophistication. And adding a contrasting colour shoe completes the modernity of this evening look.

A version of this article appeared in the September 2016 issue with the headline, “Why Don’t You…”, p. 22-23.