Then and now: These celebs and fashion insiders know how to do retro without going back in time

Then: Mary Pickford
Also known as “Little Mary,” Canadian actress and producer Mary Pickford took the ’20s by storm, appearing in numerous silent films such as Pollyana, Rosita, and Sparrows. Her curly brown hair and laidback style epitomize the relaxed attitude of the ’20s. Following the First World War, fashion loosened up (quite literally) leaving behind the constricting garments of centuries past. The drop waist was born and straighter, body-skimming dresses became the vogue. A long string of pearls up the sweetness of Pickford’s flowing dress.

Photography: Mary Pickford by Kate Gabrielle

Now: Kirsten Dunst
The drop waist has been reinvented countless times now since its inception in the ’20s. Kirsten Dunst looks anything but outdated in the sometimes body-neglecting cut. Like Pickford’s look, Dunst opts for a detailed dress that catches the eye. The high neck keeps the look sweet and ensures that things don’t get overly sexy. Yet the Melancholia star still manages to look flirty and feminine because of the light and sheer fabric, floaty squares, and her popping red lips.

Photography: Kirsten Dunst by Dave M. Benett/Getty Images

Then: Josephine Baker
Before Spring 2011, when a number of designers printed their clothing with fruit, there was Josephine Baker. The performer was notorious for dancing at the legendary Folies Bergères in Paris in a skirt made of faux bananas. The unravelling of women’s dress codes meant the ’20s held a degree of female emancipation. As an early sex symbol, Baker can be considered an important figure in relation to the newfound freedoms offered to women during the decade, as well as in a broader history of sexual liberation.

Photography: Josephine Baker by velvettangerine

Now: Giovanna Battaglia
The fashion world went bananas for Prada’s fruity Spring 2011 prints. Editor Giovanna Battaglia, wears a shorter version of the hugely popular skirt that was shown on the runway for a more youthful look. Kudos are owed for the purple sandals and bag, the perfect complement to the unripe bananas. Although Battaglia’s black top and stockings are more covered up than Baker’s stage ensemble, the overall look channels the fun, carefree attitude that the performer represented.

Photography: Giovanna Battaglia by Venturelli/Getty Images

Then: Greta Garbo
Swedish actress Greta Garbo exemplified the sophisticated style of the ’30s. After a more laid-back period of relaxed cuts, fashion returned to structure. Hemlines were elongated a few inches, and new emphasis was placed on the shoulder. Garbo’s covered-up torso shows just how serious a turn dressing took during the decade. Still, the extended line of her puffy shoulders attests to the fact that high drama and exciting design weren’t sacrificed for austerity alone.

Photography: Greta Garbo by Vintage-Stars

Now: Hailee Steinfeld
As precious as Greta looked in her big shoulders, dare we call the look a bit busy for today. So when attempting the trend, it’s best to keep things simple. Fourteen-year-old film and fashion darling Hailee Steinfeld takes the right course pairing her white, pleated top with a simple, black, high-waisted pencil skirt. Although Steinfeld’s sleeves are softer than Crawford’s, they’re still squared off and reminiscent of the late ’30s. By not piling on the jewelry and opting to leave her hair down, Steinfeld’s look is sophisticated yet doesn’t overshadow her youthful features.

Photography: Hailee Steinfeld by Jon Kopaloff/Getty Images

Then: Ginger Rogers
The structured shoulder that gained popularity in the ’30s continued on into the ’40s. Accompanying it, though, was a curvier, waist-defining silhouette, one that accentuated the hips and bust. Hollywood starlet Ginger Roger’s jacket may be boxy at the shoulders, but a nipped waist ensures that her figure isn’t lost. In true ’40s style, traditionally masculine elements such as suiting fabric and heavy tailoring are given more feminine appeal with a curvaceous cut.

Photography: Ginger Rogers by danceonair1986

Now: Kate Middleton
Kate Middleton effortlessly channeled the ’40s in the red coatdress she wore on the last day of her Canadian tour. The slightly structured shoulder didn’t overwhelm her frame, while the A-line skirt added some playfulness to the formal outfit. Keeping accessories neutral was a good call, so they didn’t compete with the rich shade of the dress. All in all, the entire look is feminine and refined but not aging for the young duchess. 

Photography: Kate Middleton by Chris Jackson/Getty Images

Then: Grace Kelly
When you think of old Hollywood, Grace Kelly instantly comes to mind. Whether it’s because of her classic beauty or timeless fashion sense, the actress is the epitome of the post-war optimism and the glitz and glam associated with cinema’s Golden Age. Stylewise, the ’50s meant a shift away from boxier practical wartime clothing to more decadent womanly shapes. Christian Dior’s New Look (narrow at the torso with a voluminous skirt), which emerged at the end of the previous decade, played a huge role in influencing trends. Kelly’s head-turning dress is perfectly matched with demure pearls and white gloves.

Photography: Grace Kelly by ___carmendy

Now: Katie Holmes
Despite flattering virtually any figure, a full skirt can be tough to pull off just because of how nostalgic and precious it can look. So how to wear volume on the bottom without looking like a retro housewife? Take a cue from Katie Holmes. The actress keeps her look current by choosing a dress with a simple top that reveals just enough skin. Holmes also avoids looking too sweet by opting for basic black and accessorizing with classic pointy-toed pumps.  

Photography: Katie Holmes by John Shearer/Getty Images

Then: Twiggy
British model Twiggy’s wide-eyed androgynous beauty emerged in sharp contrast to the proper ultra-feminine look that was popular in the early ’60s. A fresh face, neatly combed short hair, and long eyelashes made for a look that was pure, youthful, and a mainstream manifestation of mod aesthetics. The model was often seen in clothes characteristic of the subculture like straight-cut trousers and dresses, low-slung belts, miniskirts, and flat shoes. Although waifs saturate runways today, at the time Twiggy’s slender frame offered an alternative view of femininity.

Photography: Twiggy by Ron Galella/Getty Images

Now: Michelle Williams
Okay, comparing Michelle Williams to Twiggy may seem a bit obvious on account of the shared short blonde locks. Really, though, what we’re focusing on is the outfit. The actress is able to get a look that’s reminiscent of the supermodel without looking like she’s about to head out for some go-go dancing. The grey dress is simple in cut and flatters Williams’ figure without drawing too much attention to it. Also key is the above-the-knee length; any shorter and the look would have been at risk of losing points in elegance. Finally, the contrasting black sleeves add just the perfect graphic pop while staying true to the minimal appeal of the look.  

Photography: Michelle Williams by Charles Eshelman/Getty Images

Then: Jane Birkin
Emerging as an actress during the late ’60s, sex symbol Jane Birkin was still a force to be reckoned with throughout the ’70s. Serving as muse to Serge Gainsbourg, Birkin even collaborated with the singer on projects such as the controversial single “Je t’aime… moi non plus.” But it really is her sense of style that’s given the actress/singer a significant place in fashion memory (how many stars get an iconic Hermès bag named after them?) Here she looks incredibly effortless and casual in a simple white tee tucked into cuffed denim flares. That adorable basket’s just the right finishing touch to this easy summer look.  

Photography: Jane Birkin by Jerine Lay

Now: Claudia Schiffer
Supermodel Claudia Schiffer gets the flared jean right by coupling her pair with a pale yellow button up. Although cuffing your jeans like Birkin during the warmer months may be tempting, the look can risk shortening your legs. Although Schiffer probably doesn’t have to worry about cutting off her long limbs, the long, lean style she chose further elongates them. You should also pay attention to her medium wash: light enough for summer and a bit boho, yet dark enough that most figures can pull it off.    

Photography: Claudia Schiffer by Simon James/Getty Images

Then: Madonna
When it comes to pop icons few rival Madonna as influencers and in terms of sheer stardom. The superstar has been reinventing herself for almost three decades now and doesn’t seem to be stopping anytime soon. Even though the infamous Jean Paul Gaultier –designed cone bra technically only made its appearance during 1990s Blond Ambition tour, we still feel the look represents the over-the-top excess of the previous 10 years. The extreme lingerie still seems to stand for the Madonna of the ’80s and all that eroticism and controversy with which the singer was synonymous.  

Photography: Madonna by Jim Smeal/Getty Images

Now: Daisy Lowe
Model Daisy Lowe was seen front row at Jean Paul Gaultier’s recent couture show paying homage to the designer’s Madonna moment. Less costumey than the original, the cones on this fitted, sexy, pale pink number are not nearly as exaggerated. The look is also more formal, as its length almost reaches the floor, turning lingerie into an outfit appropriate for evening. Ensuring that Lowe looks completely right for 2011 and not the end of the ’80s are her unfussy locks adding to the overall sex appeal.  

Photography: Daisy Lowe by Eric Ryan/Getty Images

Then: Chloë Sevigny
With grunge, scrunchies, and crop tops all characterizing ’90s fashion, it’s hard to pick out a single unifying element from the decade. One term that does stick out is “practicality.” In reaction to the extravagant big hair, puffy shoulders, and sequins of the ’80s, the ’90s were about stripping away excess and paring looks down. Actress Chloë Sevigny achieved “It girl” status during the decade because of her choice of interesting offbeat film roles and easy effortless style. Her little black dress paired with an oversized jacket screams minimalism without being boring.

Photography: Chloë Sevigny by Ron Galella/Getty Images

Now: Chloë Sevigny
It girls come and It girls go, but it seems like we’ll always have Sevigny to look to for style inspiration. Why does she have such staying power? If we’re just talking clothes, then it has to do with her ability to not let age get the best of her. At 36, Sevigny is still able to pull off almost any outfit better than a 20-something can. Just look at the way she manages to dress down a short knit black dress with a denim jacket and fringe vest. And those black square-toed booties? Oh-so ’90s. 

Photography: Chloë Sevigny by Alberto E. Rodriguez/Getty Images