From Anna Wintour’s indestructible bob to Anna Dello Russo’s obsession with feathers, fashion’s inner circle are known as much for their style signatures as their ability to influence others. We invited two authorities with differing perspectives to analyze the distinct looks of the aforementioned tastemakers. Author Robb Young makes a study of the loaded dress codes of female political figures in his new book Power Dressing: First Ladies, Women Politicians and Fashion, unpacking everything from Michelle Obama’s J. Crew-helmed casual revolution to Carla Bruni-Sarkozy’s sophisticated embrace of Dior; Leandra Medine’s witty Man Repeller blog dissects the fashion statements women love and men love to hate—from harem pants to clogs. The conversation that ensued takes on industry power dressers Daphne Guinness, Diane Pernet and Emmanuelle Alt.

Robb Young: I’ve always felt like [Vogue Japan editor-at-large] Anna Dello Russo was tutored in a dress-up school where Isabella Blow was headmistress and Anna Piaggi was teaching physical education. If it’s not flyaway feathers it’s a watermelon hat. There’s something powerful about not taking your look too seriously.

Leandra Medine: Let's also note that RuPaul likely played the role of fine arts teacher. [Dello Russo] wears gilded apples on her head. One highly respected man repeller indeed.

RY: That’s something [American Vogue editor-in-chief] Anna Wintour would never, ever do. With her fur stoles and floral frocks, she’s a walking advertisement for appropriateness. But she still makes a visual impact. I think it’s the helmet hair. No doubt it’s as soft as alpaca, but the way that the impenetrable bob frames her sunglasses always makes me think of NASA-approved headgear with a bulletproof visor.  

LM: I do commend her for making outfit repetition a societal norm. As to her hair, three words: Dora the Explorer. And I mean that with utmost respect!

RY: If anyone beats Anna in the hair department, it’s our lady of perpetually shaded blackness, [editor of influential blog A Shaded View On Fashion] Diane Pernet. There’s such fortitude in that silhouette of hers. She’s magnetic and aloof, austere and decadent. Contradictions like that spell power, if you ask me.

LM: Diane Pernet is my queen of darkness, the substance of which my dark abysmal insides are made. If anyone knows how to garner attention, it’s D. 

RY: And when style eccentricity runs through blue-blooded veins, it's always a traffic-stopping combination: step forward the chaos of [socialite] Daphne Guinness’s canvas. I just saw her at the Charlie Le Mindu show in London looking as refined as ever. When a woman with as delicate a figure as hers can stomp around in those alien McQueen hooves and still look both elegant and ferocious, it says a lot.  

LM: Daphne Guinness? Refined? That's a name and adjective I never thought I'd see in one sentence. Unless the sentence was Daphne Guinness is the antithesis of refined. How a woman could wear heelless Nina Ricci shoes with ensembles that resemble vertebrae and still manage a busy love life and a romp or two is mind-boggling. In a good way.

RY: If you thought my sense of refinement was unique, you might think I've lost the plot when I say I think there’s more than just discipline in [Vogue Paris editor-in-chief] Emmanuelle Alt’s look. There’s a touch of decadence, too. In her world, wearing a cornucopia of the wildest runway looks would be the default, but, instead, she dares to wear “comfy rock-n-stroll” every day. It says, “I'm a natural authority and I don’t need to prove it.”  

LM: I'm on the same page as you on this one. Her monochromatic tendencies—which only include the crème de la crop of designer labels—speak lengths to her personal style. She spares no expense on the flimsiest of cotton tees, which goes back to your point about her touch of unusual decadence. I'm looking forward to watching her rule the new Vogue throne.