Gabriel Held’s B*tchy Best Dressed: Oscar Edition

Instagram’s “king of the throwback” Gabriel Held walked us through the Oscar archives for a list of the best dressed women in the history of the Academy. Here are his pointers and analysis of the best Oscar looks ever. Buckle up.

1. Go for Oscar gold

Some say “dress for the job you want” and if that job is Academy Award-winning actress, it doesn’t hurt to emulate that statuette you so desire in your wardrobe choices.

I would not, however, recommend trying to match your spray tan or injectables to Oscar’s poreless golden complexion. Look to these ladies for inspiration.

Farrah seems like the quintessential golden girl. I know she inspired me and countless other victims to experiment with Sun-In.


This must have been a learning experience for Nicole’s then-husband Tom Cruise, who has only been seen with women in flats since.


Cher and designer Bob Mackie make magic — but they also make a lot of worst-dressed lists. I disagree!


Julie Christie actually made this dress herself. I love that. It reminds me of when Aaliyah wore an off the rack dress to the Oscars.

2. Cultivate a squad — strategically

Sometimes a high-powered gal pal can be not only the best date, but the best accessory. Ditch the chiffon shawl, and pick up a star of equal or preferably lesser fame than yourself.

What better way to show your confidence than to befriend your competition? It’s what I refer to as “the Beyoncé method.” Make your competitor your collaborator, and if you happen to eviscerate them, do so graciously.

Is this a cynical take on what might just be strong female friendships? Perhaps, but we are discussing Hollywood after all. You may not have seen “All About Eve,” but I know you saw the Gwyneth and Wynona story.


Drew and Liv I buy as a genuine friendship – girl power IS the Drew Barrymore brand and Liv Tyler was the Epitome of cool girls in the 90s.

I’d rather not sully the memory of the “First Wives Club” by speculating that these women aren’t as close as the group of girlfriends that they portrayed in the movie. But. You know.


Courtney Love and who? It’s British socialite/photographer Amanda De Cadenet, but you get my point. I will love them forever for bringing this dime-store tiara and vintage slip dress aesthetic  to my attention, but what I love more is Courtney’s knack for keeping herself the center of attention by pairing up with a relative unknown.


Madonna and Fiona Apple – I see more than I’d like to of one of them, and less than I’d like to of the other. Let’s leave it at that.


Geena Davis and Susan Sarandon – Thelma and Louise: the sequel. This time it’s everybody else who dies.


Angelina Jolie and Cate Blanchett – this moment I also believe as a genuine one. They are two magnificent creatures, magnificent enough to appreciate each other instead of repel each other. Mostly because they’ll never both be up against each other for the same role.

3. Look to the past

Vintage Oscar looks can teach us what “works,” but what’s right for Elizabeth Taylor may not be what’s right for you, especially if you’re not Elizabeth Taylor, and I happen to know you’re not. Vintage-inspired looks work… when they are a reinterpretations , not simply reiterations of the past, which is really just a costume.

Old Hollywood is a wealth of inspiration. If you (or your stylist) cant be inspired , perhaps you (or they) should be retired. Here are some looks that are worth copying today.

Time for a history lesson: by 1970s standards, Racquel Welch was a voluptuous, bronzed, ethnically ambiguous dark beauty. Today she’d be considered whiter than white. How far we’ve come! She still looks amazing.


Lauren Hutton: the quintessential all American girl of the 70s wearing Halston, the quintessential American designer of the 70s. Compared to today, this is a completely effortless look. It reminds me of something Christian Lacroix once said about striving to give his gowns the appearance that they are barely draped on the wearer and could fall off at any minute.


Barbra Streisand and I have a lot in common: we’re both glamorous, Jewish, and from Brooklyn. This is another staple of the worst dressed lists , and also a staple of the most iconic Oscar looks of all time lists. I think the one is worth the other. The look was designed by the legendary Arnold Scaasi. P.S. sheer pants are huge right now!

Elizabeth Taylor, the pinnacle of glamour. She was dressed here by prolific Hollywood costumer Edith Head. This was a common practice at the time, but I doubt it ever happens in the present. It reminds me of what Dorian Corey said in the documentary “Paris is Burning.” Something along the lines of, “Nowadays it’s all about designers, and labels, about what you can buy… Or acquire… Somehow… not about personal creativity.” Also one cannot ignore the three gorgeous gems she’s displaying on her chest.


Cher – probably one of the most iconic midriffs in history, alongside Britney Spears. I would love to see the turtleneck and skirt look on somebody current. Are you listening Zendaya???


Diane Carol: isn’t it strange to see an actress of color with an Academy award 40 years ago, knowing that it’s a literal impossibility that one will win one this year?


Ann-Margret – one of the only redheads I love, not that you can tell here. Rihanna should mimic this look. Nobody else need apply.


Anjelica Houston – what can we learn from her? Be Hollywood royalty, a former model, and a movie star’s girlfriend, and do all of the above uniquely.

4. Be a supermodel trophy date

There’s no shame in riding someone else’s coattails all the way to the Oscars. Dating your way to the top takes a special kind of talent, after all. You’ll have a leg up if you’re a model.

Just be a real-life Bond girl and a ticket to the Oscars is yours for the taking, as Claudia and Naomi prove here.

5. Be a fashion “faux positive”

Sometimes, the “worst dressed” have the most success at creating iconic moments. Considering The notion of the ” fashion police,” I couldn’t help but wonder: What qualifications are required to become a professional “fashion policer”? Having an opinion?  A thirst for public attention? The ability to somewhat coherently string a series of words together?

In what other profession are these “qualifications” considered adequate to make one an authority? Fox News correspondent? Republican presidential candidate? If everybody dressed for the fashion police, we would have lost out on some major moments!

For instance, Bjork’s iconic swan dress. That’s what I refer to as a “fashion faux positive.” Whether people loved or hated that look, we’re still discussing it 15 years later, and the value of that kind of cultural contribution is something that cant be underestimated. It’s as famous at J. Lo’s Versace dress.

Juliette Lewis – I. Love. This. Look. Mixing two totally disparate sensibilities always makes something new. It also fits with her image, and I can’t help but read it as a subtle F you to Hollywood. I also love braids and think they’re appropriate everywhere (ahem Giuliana Rancic), as well as a gold doorknocker earring. Honestly.


Without a doubt my all-time favorite Celine Dion look. The tux may have been backward, but the look was very forward. Also backward: all the people who consider this one of the worst Oscar looks in history. I don’t know how intentional this was, but taking such a classic red carpet visual as a tux, and not only flipping it by changing the typical gender of the wearer, but by literally wearing it backwards is so subversive and so John Galliano.


Liz Hurley and Pamela Anderson – what I like about Pamela here is she knows who she is and she’s not trying to pull one over on us, unlike some celebs who will show up in a classic Old Hollywood glamour look and try to be slick when it’s just not them.


Lizzie Gardiner in hands-down my all time favorite Academy Awards look, no question. The designer of the costumes from the visual feast that is Priscilla Queen of the desert, made this look work on every level for me. First of all, she’s doing essentially what everybody else is doing, she’s just being literal about it by wearing actual AmEx cards. When people come dripping in Harry Winston Jewels with armed guards what are they saying? Money money money. She’s just being more up front about it, and lovingly mocking fashion. Also, taking a relatively Mundane item and transforming it into a red carpet gown  as she has done here with American Express Gold card is genius. There’s transformative potential and everything and it takes real creativity to actualize it.


The South Park guys – this is a perfect illustration of what I said earlier. What worked for Gwyneth Paltrow and Jennifer Lopez might not work for you if you’re not Gwyneth Paltrow or Jennifer Lopez. That being said, this red carpet look is almost as famous as the ones it’s imitating. This is totally on brand for them and it’s really committing to the bit.

6. Ask yourself: WWJS?

The final golden rule: what would Joan say? You may want to ignore this hypothetical critique, but if you have a sense of humor and imagination, you can at least have a hearty lol at yourself, and that is my final tip!


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