Because of her position, Wintour's wardrobe is often closely scrutinised and imitated.
Earlier in her career, she mixed fashionable T-shirts and vests with designer jeans.
When she started at Vogue as creative director she switched to Chanel suits with miniskirts.
She continued to wear them during both pregnancies, opening the skirts slightly in back and keeping her jacket on to cover up.
Wintour was listed as "one of the fifty best-dressed over 50s" by The Guardian in March 2013.

According to biographer Jerry Oppenheimer, her ubiquitous sunglasses are actually corrective lenses, since she suffers from deteriorating vision as her father did.
A former colleague he interviewed recalls trying on her Wayfarers in her absence and getting dizzy. "
I think at this point they've become, you know, really armour," Wintour herself told 60 Minutes correspondent Morley Safer, explaining that they allow her to keep her reactions to a show private.
As she rebounded from the end of her marriage and the turnover in the magazine's editorial staff, a fellow editor and friend noted that "she's not hiding behind her glasses anymore.
Now she's having fun again."
Because of her position, Wintour's wardrobe is often closely scrutinised and imitated. Earlier in her career, she mixed fashionable T-shirts and vests with designer jeans. When she started at Vogue as creative director she switched to Chanel suits with miniskirts. She continued to wear them during both pregnancies, opening the skirts slightly in back and keeping her jacket on to cover up. Wintour was listed as "one of the fifty best-dressed over 50s" by The Guardian in March 2013.
According to biographer Jerry Oppenheimer, her ubiquitous sunglasses are actually corrective lenses, since she suffers from deteriorating vision as her father did. A former colleague he interviewed recalls trying on her Wayfarers in her absence and getting dizzy. "I think at this point they've become, you know, really armour," Wintour herself told 60 Minutes correspondent Morley Safer, explaining that they allow her to keep her reactions to a show private. As she rebounded from the end of her marriage and the turnover in the magazine's editorial staff, a fellow editor and friend noted that "she's not hiding behind her glasses anymore. Now she's having fun again."
Anna Wintour