The Most Stylish Women Ever

"Jackie Kennedy is the classic American style icon."

Bing: Jackie Kennedy's fashion style

"Marilyn Monroe is famous for the billowing-white-dress moment, but for me it was her more casual sexiness that I remember: a pair of jeans and a white oxford shirt."

Bing: Marilyn Monroe's most popular styles

"Not only is Beyoncé a trendsetter with her effortless look, but she is a true role model for so many young women."

"Ali MacGraw's unconventional simplicity in The Getaway, with Steve McQueen, was fantastic. She has a special way of drawing you in."

Bing: Ali MacGraw's most popular fashion picks

"Grace Kelly is the princess of class. She is timeless and the ultimate definition of charm."

Bing: Grace Kelly's style

Lucky's Picks From the Icon Collection: Offering up 25 flawlessly rendered pieces, this entire limited-edition mini line telegraphs the deeply American aesthetic that Hilfiger has made his own.

This shawl-collar fisherman's sweater is so Cape Cod–at-its-chicest.

Cashmere-blend "Ay Ay" sweater, $128 (avail. late Sept.), Tommy Hilfiger 25th Icon Collection, tommy.com

Lucky's Picks From the Icon Collection: A brilliant—and insanely cool—update on the cowboy boot.

Leather Cowboy Boots, $228 (Avail. late Sept.), Tommy Hilfiger 25th Icon Collection, tommy.com

Lucky's Picks From the Icon Collection: Crisp and oversize but tailored exactly where it counts.

Cotton Boyfriend Shirt, $88 (avail. late Sept.), Tommy Hilfiger 25th Icon Collection, tommy.com

Lucky's Picks From the Icon Collection: Perfectly slouchy and worn-in, these already look like your best-loved jeans.

"Girls Crazy Horse" jeans, $128 (avail. late Sept.), Tommy Hilfiger 25th Icon Collection, tommy.com.