The 10 Best Fashion Moments of the 2020 Oscars

Last night, the 92nd Academy Awards concluded the 2020 awards season and to say the least, it ended with a bang. My favorite moment about this year’s Oscars was seeing Matthew A. Cherry, director of Hair Love, win the Animated Short category, and Bong Joon Ho, director of the movie Parasite, sweep the night with 4 wins including Best Picture.

For the academy to recognize these directors of color and give them the recognition they deserve for their amazing work was momentous. It really highlighted the fact that representation matters and different perspectives bring a fresh lens to screens across the globe.

This was also a night full of amazing performances including the opening number from Janelle Monae, Randy Newman’s sentimental Toy Story 4 piece, and Billie Eilish and Cynthia Erivo snatching hairlines from the front to the back of the Dolby Theater in Hollywood.

Furthermore, the night was full of some beautiful (and not so beautiful) fashion moments. But here we are going to focus on the best of the night! Here are my top 10 fashion picks from this year’s Oscars ceremony.

Saoirse Ronan

Screen Shot 2020-02-10 at 1.36.58 PM
Gucci gown

This gown is absolutely beautiful and the pop of lavender on the train really gives it some character! It’s a fresh take on a classic silhouette.

Janelle Monae

Screen Shot 2020-02-10 at 1.40.23 PM
Ralph Lauren gown and headpiece with Forevermark jewelry

This is a gown fit for the Oscars. Janelle always makes bold fashion choices and pulls them off effortlessly!

Scarlett Johanssen

Screen Shot 2020-02-10 at 1.42.27 PM
Oscar de la Renta gown with Forevermark jewelry

Scarlett didn’t come to play! This dress is divine. The academy might as well remake the Oscar statue with this as the inspiration. You go Glen Coco!

Charlize Theron

Screen Shot 2020-02-10 at 1.44.57 PM
Dior Haute Couture gown with Tiffany & Co. jewelry

This silhouette is absolutely gorgeous. It’s classy, yet sexy and shows that sometimes all black makes more of a statement than bright hues or lots of skin.

Cynthia Erivo

Screen Shot 2020-02-10 at 1.46.49 PM
Versace gown, Maria Tash accessories, and Stuart Weitzman heels

What can I say? Cynthia killed this look! The all white gown against her beautiful brown skin looks magnificent and she wears it effortlessly.

Renée Zellweger

Screen Shot 2020-02-10 at 1.48.39 PM
Armani Prive gown, David Webb jewelry, and Jimmy Choo heels

This sleek, white, one shoulder number is so flattering and it compliments her figure perfectly. It’s simple, but makes a beautiful statement at the same time.

Mindy Kaling

Screen Shot 2020-02-10 at 1.50.37 PM
Dolce and Gabbana gown with Chopard jewelry

Bright colors always compliment darker skin tones very well. This color is perfect for Mindy and reflects her personality even better!

Camila Morrone

Screen Shot 2020-02-10 at 1.53.07 PM
Carolina Herrera gown with Tiffany & Co. jewelry

This gown is so dreamy! It actually started out as a wedding dress that was then redesigned for the red carpet. It compliments her figure very well and it feels like a nod to the renaissance-age, while adding a modern perspective.

Regina King

Screen Shot 2020-02-10 at 1.57.40 PM
Versace gown with Harry Winston jewelry

Regina walked in like she was worth a million bucks! And she basically was! Her Harry Winston jewels alone were worth upwards of half a million dollars. This Versace dress fits her like a glove and the pink hue compliments her skin tone gorgeously.

For the last look on this list, here’s what I wore to the Oscars!

Arielle Winfield


I chose to wear a jumpsuit because it’s an unexpected silhouette for a red carpet. Usually you see gown after gown after gown, but I wanted something that would stand out. The perfectly designed details and all over sequins really elevated the look and made the outfit red carpet ready.

This beautiful jumpsuit was created by the talented opera singer, composer, and fashion designer, Radmila Lolly. We collaborated on the design and she customized it perfectly. The details are so stunning and the peekaboo mesh segments give it a character of its own. The jumpsuit turned out absolutely beautiful and I got at least a million compliments on both the outfit and my hair!

If you’re looking for an amazing Los Angeles based hairstylist, definitely go check Chrissan out! She’s so talented and takes great care of natural hair.

Honorable Mention

I couldn’t end this post without mentioning another look of the night that absolutely blew me away…


Screen Shot 2020-02-10 at 4.42.13 PM
Ralph and Russo gown

Since Ciara wore this look to the Vanity Fair Oscars after party I couldn’t include it in the list, but I absolutely had to highlight it because…. just look at her! *insert a thousand heart eye emojis*

So, what do you guys think? How did my look stack up against all these Hollywood stars? Leave a comment below!

xoxo, Arielle


life style blogger

5 thoughts on “The 10 Best Fashion Moments of the 2020 Oscars

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.