Best Dressed Oscar Looks of All Time

Now that awards season is in full gear and one of Hollywood’s (and fashion’s) biggest nights is just around the corner, I feel compelled to do a fashion round-up of some of the Oscar’s most iconic looks. Back in the day, celebrities didn’t always wear gowns or couture looks from the top 10 design houses. There was no such thing as a “Best Dressed” list so people took more risks, and the fashion choices celebrated individuality and personal style. I chose 11 women who either exemplified beauty, taste, risk-taking, individuality, or all of the above. As a stylist, I always gravitated towards collaborating with artists known for risk-taking and self-expression. Naturally, when thinking about my blog post and what I wanted to write about, I gravitated towards the more eccentric and unique, because for me, that is when fashion is at its best. 

In addition to my Oscar roundup, I've called out what undergarments you would wear with each look--just in case you have pieces like these in your closet. So take cues if you have similar silhouettes at home. I'm here to make getting dressed more enjoyable--because it doesn't have to be a complicated struggle! 

I support you. 

xo, Simone

Audrey Hepburn is one of my all time fashion icons. She had an elegance and grace that was just innate.  Her iconic gamine style complemented her frame and made everything she wore pure perfection. When she took home best actress for her role in “Roman Holiday” in 1954, Hepburn wore a white lace gown by her favorite designer Hubert de Givenchy. The two had a long-standing friendship and work relationship, but this was her first time wearing his designs publicly. 

Undergarment recommendations
Top: For bigger breasted women, I recommend our Convertible Push-up BraFor women who don’t need as much support, I recommend our Bandage Tape or no bra at all.
Bottom: High-Waist Brief


Grace Kelly wore a satin mint green gown designed by the famous costume designer, Edith Head, when she won her Oscar for best actress in “Country Girl” in 1955. 

Undergarment recommendations
Top: Same as above. For bigger breasted women, again, I recommend our Convertible Push-up Bra. And for women who don’t need as much support, I recommend our Bandage Tape or no bra at all.
Bottom: High-Waist Thong


Barbra Streisand took home an Oscar for “Funny Girl” in 1969 in a sheer tuxedo pantsuit designed by Arthur Scaasi. She apparently didn't know the suit was sheer until the lights hit her once she was on stage. 

Undergarment recommendations
Top: I recommend Petal Pasties, Bandage Tape, or go free! 
BottomTap Short, no question.


Diahann Carroll’s light pink fitted empire waist gown with sheer crystal overlay in 1969 makes my decadent 60’s fantasies come true! And it was the perfect prelude to where fashion headed in the 70s. 

Undergarment recommendations
Top: I recommend the Molded Plunge Soft Bra
Since this gown is loose and not figure-hugging, I would go with the underpant of your choice. Personally, I am a brief girl. My body never met a thong it liked, so I would probably go with the Seamless Classic Cut Brief or the High-Waist Brief.


Ann Margaret stole the show in 1974 when she wore this beaded gown with rhinestone-embellished hood. I trolled the internet and there were no full-length images of this look, but you get the picture with this close-up photo.

Undergarment recommendations
Top: I suggest using Bandage Tape for necklines that don't allow for bra straps. Or, if you need more support, the Convertible Push-up Bra
This dress seems pretty tight to the body, so I would suggest our Seamless Thong.


Lauren Hutton wore Halston to the Oscars in 1975. This look is chic and head-turning, yet not over the top, making it timeless. In fact, this look is still widely referenced in fashion today.

Undergarment recommendations
This gown has a pretty sheer and narrow neckline, especially at the shoulders. I would suggest our Petal Pasties.
Bottom: And of our seamless underwear in Sand.


Diane Keaton had an innate sense of style that was all her own. Her iconic pant suit looks were “borrowed from the boys,” but perfected with quirky and unexpected accessories and proportions.  It one-up'd them. That individuality was shown through in the character Keaton played in Annie Hall. Her character’s fashion was Keaton’s own and thanks to her, it changed the standard for female fashion and the definition femininity. Here’s a picture of Diane Keaton at the 1978 Oscars, where she won Best Actress for “Annie Hall.”

Undergarment recommendations
Since Diane’s look doesn’t show skin and is pretty loose, I say wear what you feel most comfortable in! That’s always the most important choice!



The all-time Oscar fashion winner for me would have to be Cher. She has had so many iconic Oscar looks, it wouldn’t be fair to just pick one. Above are a few of my favorites...

Undergarment recommendations
Since all of Cher’s looks are fairly revealing and skimpy, I suggest going with the bare minimum here. Our Adhesive Thong would do the trick for all these looks.


Madonna and Michael Jackson turned heads when they went as dates in 1991. Michael dressed as himself in a beaded white blazer and Madonna channeled Marilyn Monroe in this white beaded Bob Mackie strapless gown.

Undergarment recommendations
Top: A sweetheart neckline usually presents a challenge, even with strapless bras. I would suggest no bra, but if you need extra support here, try our Bandage Tape. You can be sculpt and shaped the tape to fit your desired neckline.

Bottom: I suggest a Seamless Thong for a tight, form-fitting dress to avoid any major VPL. 


Gwyneth Paltrow was pure pink perfection when she won best actress in 1999 for her role in “Shakespeare in Love." This look was thoughtfully executed with tempered elegance. From her severe side part hair, to her diamond choker, Paltrow stole the show in this pink Zac Posen gown.

Undergarment recommendations
Top: I would suggest no bra, but if you need extra support here, try our Bandage Tape. 
Bottom: Because the gown is not fitted around the hips, I suggest our Seamless Classic Cut Brief or Seamless Thong


Charlize Theron channeled Hollywood glamour when she wore this Gucci gown to the Oscars in 2004, when she took home the Oscar for best Actress in the movie “Monster.” The look was the antithesis of the character she played in the movie. It was simply dazzling paired with diamond cuff and old Hollywood waves.

Undergarment recommendations
The top of this dress does not really allow for any undergarments, because the cups are small.
Bottom: Because of the low back and the lightweight fabric, I recommend our Adhesive Thong.