NOW Mess it up a bit. With spiky asymmetrical pieces on top (a la Halle Berry), the new pixie is more forgiving than the flat, boy-cut versions of the past, says Mancuso.
THEN Twiggy's chic runway style in 1967.
INSIDER TIP This style works best with a small face.
NOW "Don't take the flip too seriously," says N.Y.C. stylist Kevin Mancuso. "Instead of the ends flying out like Mary Tyler Moore's they should barely hint at an upturn."
THEN Mary Tyler Moore's feathered flip, 1970s.
INSIDER TIP Take a cue from Michelle Obama's style: adding in layers and an undefined part can soften the formerly structured style.
NOW "Keep locks longer, almost to the shoulders, so they're choppy in the back and even and angled in front," suggests L.A. stylist Mark Townsend, who recently cut Ashley Olsen's hair.
THEN Molly Ringwald's short style in 1986.
INSIDER TIP For an elegant effect, flat iron hair starting a few inches from the scalp.
NOW Ditch the Pebbles Flintstone height. "These days, ponytails are low and streamlined," says Townsend, who recommends smoothing hair before securing it a few inches above the nape of the neck, like Debra Messing's.
THEN Pebbles Flintstone's spunky ponytail, 1960.
INSIDER TIP Add polish to the sleek style, wrap hair around the elastic.
NOW Waves are smoother like Sienna Miller's, which means trading in your beach spray for a shine pomade. "The effect now is glossy soft, and a bit more refined than the messy waves we've been seeing in recent years," says L.A. hairstylist Adir Abergel.
THEN Farrah Fawcett's signature style in 1976.
INSIDER TIP For a relaxed wave the curl should start below the ear-line.
NOW Play up the shag's rock and roll vibe with choppy layers like Taylor Momsen's, but "keep them on the straight side," suggests Abergel. "You don't want too much body."
THEN Jennifer Aniston's famous style from her days on Friends in 1995.
INSIDER TIP Try not to overstyle it, adds Mancuso: "A shag is best when there's a lived-in, natural feel to it."
NOW Stars like Monique Coleman show that it's time to live large. "Big Afros are strong and sexy," says N.Y.C. stylist Ted Gibson. "The shape is somewhat abstract with uneven edges, and it's pulled apart a little bit," adds Mancuso.
THEN Whitney Houston's short and curly style in 1986.
INSIDER TIP Keep styling products to a minimal this style should seem organic.
NOW "Keep it loose and touchable—not like the crunchy look of the '80s," says Townsend.
THEN Glenn Close's blonde curls in 1987.
INSIDER TIP Spirals like Leighton Meester's should also start lower on the head (around the ears as opposed to the scalp). This leaves the top of the head smooth, so you avoid the dreaded pouf.
NOW Stick with something simple but polished, like Anne Hathaway's low bun. The overachieving styles of Hepburn's time feel too fussy today. "Now it's gathered at the nape of the neck and twisted into a sleek shape," says Townsend.
THEN Audrey Hepburn's iconic Breakfast at Tiffany's style in 1961.
INSIDER TIP Tame hairline frizz with a dab of styling paste.
Long & Straight
NOW With volume at the roots and long, face-framing layers like Fergie's, the latest version has more movement (and less weight) than in the super-straight '70s, says Townsend: "I bend the ends of the hair as I iron it so you can see the layers more."
THEN Maureen Mccormick's Brady Bunch style in 1971.
INSIDER TIP Bend the ends of the hair as you iron it so you can see the layers more.