50 Vintage Style Dresses, Outfits, and Iconic Style Stars

Vintage style dresses evoke that kind of elegant nostalgia, which just about every woman on the face of the planet dreams of. All would-be fashionistas model themselves after one iconic style star or another, so it’s only normal that they should revere the past, with its wonderful fashions. In a certain sense, this kind of adulation for the past is the modern-day equivalent of Cinderella, looking up to her step-sisters and longing to become a princess in her own right. So, to celebrate the most beautiful, complex, and sophisticated looks in style history, today we’re bringing you the 50 most iconic, admired, and well-known style stars, in their best attire.

We cover all decades and trends, starting with the 1930s (think Ginger Rogers and Rita Hayworth), moving up through the classy 40s, the exciting 50s, the swinging 60s, the liberating 70s, the glitzy 80s, and the dramatic 90s. We’ve got movie star icons like Marilyn and Audrey on our list, but also icons from the younger generation (Gwyneth Paltrow, Alicia Silverstone, Kate Middleton, and Kate Moss, to name but a few). There are singers, royals, and even ladies associated with politics on the list. And we’ve even got a surprise male feature – included for the way he carried the dress, more than for the dress itself. Read on, enjoy, and let us know if you think we left someone out!

 

50 Vintage Style Dresses, Outfits, and Iconic Style Stars

 

1. Natalie Wood in ‘I Feel Pretty’

The dress itself might not look like much. It might even seem a bit on the frumpy side. But what’s really important about the dress Natalie Wood wears in West Side Story (1961) is the fact that she sings “I Feel Pretty” wearing it. And that is precisely the message of the movie – to accept your own identity, to celebrate your sense of personal worth (and, implicitly, your own style). Fifty years after the launch of the movie, it’s difficult to imagine anyone else in this dress, embodying Maria with as much passion and talent as the legendary Natalie Wood.

2. Great green expectations for Gwyneth Paltrow

There was quite a lot riding on the update to the screen adaptation of classic novel Great Expectations, released in 1998. Unfortunately, the movie proved to be both a commercial failure, as well as an artistic achievement of mediocre value at best. However, not everything about it is horrendous: on the one hand, the soundtrack is rather pleasant and, on the other, Gwyneth Paltrow’s outfits in the movie were entirely designed by celebrity designer Donna Karan. That’s why we get to see her character, Estella, glide about from one scene to another wearing nothing but beautifully crafted green dresses, like the one featured in the image above. The outfits perfectly complemented Paltrow’s natural good looks and added a much-needed touch of contemporary sophistication to the otherwise bland movie.

 

3. Babs goes sheer for the 1969 Academy Awards

She might not be the world’s most beautiful, but there is no denying Barbra Streisand’s presence, charisma, and sheer talent, too. The Academy of Motion Pictures also seemed to think so, when, in 1969, they nominated Babs for the Best Actress in a Leading Role award, pitting her head to head with none other than screen veteran Katharine Hepburn! Babs, who was nominated and won for her role in Funny Face dared to show up for the ceremony in an outfit that was controversial then – and would probably even raise a few eyebrows today, when it looks like there is some sort of spaghetti-strap dress uniform for female nominees. Instead, Streisand, who certainly doesn’t lack in the personality department, opted for a sheer two-piece pant suit by celebrity designer Arnold Scaasi. The outfit was surely noticed, especially for the way it glimmered, as well as for Babs’ accessorizing choices: the wide white collar and oversized velvet bow definitely work with her cute late-sixties bob haircut.

 

4. Olivia Newton John – Grease Lightning!

There are many things to be said about the way Olivia Newton John’s character Sandy, from the popular 1978 musical Grease, chooses to outfit herself. Most importantly, throughout the movie, Sandy transitions from being a typically square goody two shoes, in A-line dresses, pearls, and proper updos, to… well – what you see in the image above. Both outfits speak of values that are equally relevant for American society, even to this day. By becoming the sexy vixen at the end, who is no longer afraid to show off her street cred in the sleek black leather pantsuit, Sandy also reveals she is no longer the insecure little girl in the beginning of the movie. Newton John certainly had the figure to pull off such an outfit and also gave us one memorable song and dance number after another, alongside screen partner John Travolta.

 

5. Forever Pretty in Pink, Molly Ringwald

At the time the movie Pretty in Pink was released, in the mid-eighties (1986, to be exact), fashion critics left and right jumped to criticize what they called the horrid dress sported by Molly Ringwald’s character at her high school prom. Little did they know that the shoulder cut out dress, with mesh paneling and oversized polka dots, would come to redefine the style of the 1980s. Ringwald’s look is utterly iconic by now, complete with the tousled poufy hair – and it’s no plot coincidence that the dress is DYI – you can actually make it yourself with the aid of this tutorial. The character makes her own dress in the movie, out of a hand-me-down and something she bought at a thrift store. The end-result might not have appealed to the high-brow critics, but it certainly rang true to kids around the United States, who finally got the chance to see someone who dressed like them on the silver screen.

 

6. Julie Christie and the Zhivago look

The 1965 drama Dr. Zhivago might not say much to some of the younger generation, but, at the time, actress Julie Christie launched a global frenzy with her Russian-inspired looks. Behind them, the genius of iconic costume designer Phyllis Dalton was hard at work. Dalton managed to bring out Christie’s spectacular natural beauty, while playing up early 20^th century Russian style elements (boots, silk, and fur coats, most notably), and also factoring in hot trends from the 1960s. Many of the outfits that Christie’s character sports in the movie, as she goes on her odyssey from seamstress to nurse, went on to inspire some of the day’s biggest names in fashion design: think Dior and Yves Saint Laurent, most notably.

 

7. Clueless in Calvin Klein

Clueless (1995) is one of the more recent classics we included on our list of vintage style dresses and accessories, but we couldn’t have consciously made the decision to leave out the skimpy white mini slip dress worn by Alicia Silverstone in the movie. Perhaps the most apt description of the outfit is issued by the father of Cher Horowitz, who, upon seeing her get ready to leave the house in that dress mistakes it for underwear. This, of course, after Cher has paraded through the movie in no less than fifty different outfits, like the true blue fashionista she is. The same model dress was re-released in 2010 for the film’s fifteenth anniversary, by Francisco Costa, the creative director of Calvin Klein, and could be purchased online in white and red, for $916.

 

8. Disco sleek Michelle Pfeiffer in Scarface

Scarface (1983) is one of the best movies of all times, when it comes to gangster flicks. To boot, it’s also interesting to analyze from the point of view of costumes. Michelle Pfeiffer, for instance, spends most of the movie gliding about in long, sleek evening gowns, such as the one in electric blue featured above. There is something distinctly eighties and disco about her look – and it definitely has a lot to do with the color of the dress. Aside from that, however, the costumes also help reinforce the gangster chic charm of the 1930s, when flappers would prance about speakeasies in sequined dresses. Pfeiffer thus perfectly lends her face and figure to the character of Elvira and pulls off the look of a love interest for drug overlord Tony Montana (Al Pacino).

 

9. Kate Middleton getting engaged in Royal blue

The past two years have truly been royal: the royal engagement was followed by the royal wedding, and, of course, the famous royal baby. But it all started with the beautiful and classy blue dress that Kate Middleton, the Duchess of Cambridge, wore at her engagement with Prince William. The Issa dress is believed to have been designed in royal blue as to match the blue sapphire engagement ring, that belonged to William’s mother, the late Diana, Princess of Wales (who also features on our list!). Kate has become a style icon of sorts in the United Kingdom, which is probably why her dress was copied into infinity in High Street stores all over the country. It’s worth noting that, prior to donning the now famous royal blue engagement dress, Kate Middleton had often been spotted in Issa designs. This has actually earned her the title of ‘unofficial brand ambassador’.

 

10. Brigitte Bardot rips her skirt to do the mambo

Now, with the young Brigitte Bardot, you never know if it’s the outfit or her smoldering good looks which turn a dress into an iconic fashion statement. However, no one could really argue against how memorable this particular scene in And God Created Woman (1956) really is. In the end scene of the movie, Bardot’s character tears her green skirt all the way up to reveal her underwear and lets loose, as she dances the mambo to improvised percussion. Bardot was barely in her 20s when the famous film was shot and instantly became a star thanks to the part.