Fashion has such a big impact on our culture. From red carpets, to the Met Gala, to everyday clothing, fashion trends influence our lives whether we know it or not. I have memories of looking through magazines with my mom at the doctor’s office and pointing at which dresses I liked the best. As I got older, I started to watch red carpets for big fashion events like the Grammy awards and the Met Gala. My sister and I always text each other our favorite and least favorite outfits from the carpet. So, when I saw the 27 Dresses trend, I thought it would make for a good article. The following dresses are my personal 27 dresses of media and entertainment.
27. Hayley Williams white tour dress 2023.
This dress, while very simple, is one of my favorite looks from Hayley Williams. It is very structured and angled which I love and the stark white color definitely stands out. I couldn’t say exactly why I am so drawn to this dress, maybe it is the contrast with her hair or maybe it is the shape of the dress itself, but ultimately I love it and it is one of my favorites.
26. Madonna’s white Bob Mackie dress at the 1991 Oscars.
Next on my list is a classic. This dress from Bob Mackie is just stunning. The sparkles, the stark white color, and all the accessories that are along with it just make this dress feel so special. This entire look very much reminds me of Marylin Monroe and it has also been reimagined by Sabrina Carpenter in the more modern era. Overall, just an elegant stunning gown.
25. Sarah’s ballgown in Labyrinth (1986).
This ballgown is such a statement piece. It is simultaneously such a time capsule of the ‘80s style and yet, feels very regal and royal like something from the 1800s. This dress fits in with that dream-like, enchanted feeling that surrounds Labyrinth as a whole piece of work. I love this dress for many of the same reasons as Madonna’s Bob Mackie, its sparkly, it’s flattering, and it’s a statement.
24. Kat Strafford’s prom dress from 10 Things I Hate About You (1999).
This is one of my favorite prom dresses in any movie or show I have seen. Simple and classy, Kat Strafford’s dress is just gorgeous. The color, the shawl, the hair: it’s just beautiful.
23. Miss Scarlet in Clue (1985).
Clue is one of my favorite movies. This dress, from the first time I watched it, stood out to me. Something about it is nothing like I have ever seen. I really enjoy the combination of the dark green and the light blue. I love how it is not perfectly smooth but instead looks textured almost like it is silk or velvet. Everything about this dress is just so good.
22. Betty Hanes’ green dress in White Christmas (1954).
This dress is one that I wish I could have in my own closet. Although the shape is very ‘50s, I think that I would absolutely wear this dress if I owned it. I love the detail of the crossed v-neck. I love the velvet texture. But, my favorite part of this dress is the color. It is such a dark green that in the movie you would think it was black at most angles. However, the velvet texture allows for the true color to come out and I just adore it.
21. Princess Mia’s ballgown in The Princess Diaries (2001).
The details of this dress is truly what makes it one of my top 27. Without the gold details on this dress, it would be just another white ballgown. But, the floral, gold details just absolutely make it for me. They elevate this dress to a whole other level.
20. Eliza’s white gown from My Fair Lady (1964).
Eliza’s dress in this scene is truly the only thing I remember from watching this movie. I watched My Fair Lady many years ago and I have not revisited it, however, I adore this dress. The beaded layer is so unique and the sleeves are just gorgeous. I absolutely love the beaded design and that is what makes it one of my favorites.
19. Britney Spears’ butterfly dress at the 2002 Versace runway.
This dress is truly something special. The colors and the cut are so beautiful, yet unique to this look. There is something to be said for a dress that is renowned in pop culture and the butterfly dress definitely makes it into that category. This dress is a symbol of 2000s fashion and the Y2K era for sure, especially because it is Britney Spears that is wearing it.
18. Judy Hanes’ pink dress in White Christmas (1954).
This is another piece that I just adore from White Christmas. Honestly, I think that the dance being performed in this scene is what makes the dress one of my favorites because of the movement of the fabric. It is simultaneously flowy and stiff at the same time and looks so good on the screen. I also just love the shape of the sleeves here.
17. Arwen’s blue dress in The Lord of the Rings: The Return of the King (2003).
This is a dress that I remember seeing for the first time and thinking to myself yeah if I lived in this universe that is something I would want to wear. It is elegant and gorgeous. The texture and colors of this dress are just gorgeous. I love the way that it is somehow so simple but feels intricate and delicate at the same time.
16. Lady Gaga’s meat dress at the 2010 MTV’s VMA awards.
I think that this is the first dress I truly remember having a big impact on pop culture in my lifetime. I remember it being referenced in TV shows and interviews as a kid. I think that the impact it had is what makes it so iconic to me. I don’t actually even really like the look of it, but it is so legendary in the fashion world that it doesn’t even matter to me that I don’t love it.
15. Princess Leia’s dress in Empire Strikes Back (1980).
Yet another white gown, this dress is effortlessly beautiful and elegant. It feels royal, as it should, because of the long, flowy sleeves and the silver belt. I have always loved this dress more than any other one of Princess Leia’s looks within the Star Wars movies. I think it is underrated within the films and it deserves to be in my top 27.
14. Emma Stone’s mint dress at the 2024 Oscars.
I remember seeing this dress on the Oscars red carpet in 2024 and just falling in love with it. Emma Stone is one of my favorite actresses and this dress suits her so well. It compliments her skin tone and hair color so perfectly. It also is such a unique shape that might seem a little odd, but I actually really enjoy it. It is classy and gorgeous.
13. Rachel Green’s mint dress in season three of Friends.
This dress is one of the more famous looks from Friends. But, I think that it is famous for a reason. It is so flattering and there is an elegance to it. This dress also compliments Rachel’s skin and hair color so well. The color is not something you see in a ton of dresses but I think it is perfect for this one.
12. Stevie Nick’s dress on the cover of her album Bella Donna.
I remember being a little kid and my mom telling me that she was obsessed with this dress in high school. Looking back, I now understand that obsession. This dress has a haunting whimsy to it. The way the fabric lays makes me think it would move almost like smoke. Similar to my mom, I am obsessed with this dress in every way.
11. Emma Chamberlain at the 2026 Met Gala.
When Emma Chamberlain came out in this dress at the Met Gala I believe my jaw actually dropped. It is so creative and I have never seen anything quite like it. I love the shredded look of the sleeves. The colors and how the bottom is textured reminds me of a watercolor painting in the best way. This is one of my favorite Met Gala looks ever.
10. Carrie Bradshaw’s Christian Dior newspaper dress in season three of Sex and the City.
Sex and the City is full of iconic fashion successes and failures. This dress, I would say, is one of its greatest successes. The cowl neckline is gorgeous, the newspaper print feels perfect for the New York setting, and ultimately it is an outstanding statement piece. I love this dress and if you are looking for a show, especially if you are into fashion, I would highly recommend Sex and the City.
9. Cruella’s gown at the Black and White ball in Cruella (2021).
This gown is simply magnificent. Cruella is another piece of media chalk-full of incredible fashion moments. This, however, takes the cake to me. This dress starts out covered by a white cape which Cruella sets on fire and it burns to reveal this showstopper of a dress. I love everything about this dress, the color, the shape, the texture.
8. Zendaya’s dress at the 2018 Met Gala.
This is another Met Gala outfit that I remember being so impactful to me. When I first saw this dress, I was absolutely blown away. It is so intricate and gorgeous. I love the way it is shaped like a knight’s uniform but it is still so flattering. Zendaya is probably my favorite celebrity as far as fashion goes. She has had so many incredible looks and this one is no different. It is absolutely incredible.
7. Buttercup’s wedding dress in The Princess Bride (1987).
The Princess Bride was a staple at my house growing up. I have probably seen this movie at least 50 times and yet, every time I watch it, I find myself loving this dress. As a wedding dress, it is of course classy and elegant.
6. Zendaya at The Odyssey premiere.
This is my favorite red carpet look of this year. I think it is the perfect choice for Zendaya’s role in The Odyssey. It is so simple and yet so detailed. I love the addition of the wings and the shape of the dress is so flattering.
5. Blake Lively at the 2018 Met Gala.
This has been one of my favorite dresses for a long time. I adore the beading, the color, and just all the details. It feels very dramatic but elegant and beautiful without being too over the top. It is just so beautiful and I truly adore this dress.
4. Tyla’s sand dress at the 2024 Met Gala.
Tyla’s sand dress was another Met Gala look that had my jaw on the floor. This dress fits the theme so well and it is so creative. It feels somehow unique and also timeless at the same time and I think that is why I love it so much.
3. Sabrina Carpenter at the 2026 Met Gala.
Talk about creativity. Sabrina Carpenter’s dress made from film is just so incredible. I love every single aspect of this dress. I love how it is fitted but also draped around her at the hips and how it flows out through the train. Plus, the film being from the movie Sabrina is just an amazing added detail.
2. Princess Diana’s revenge dress.
The revenge dress, I think, speaks for itself. It may seem like a basic pick, but it is so iconic and gorgeous that I couldn’t leave it off this list. Princess Diana looks so regal and I think she definitely got her “revenge” as this dress is still culturally significant to this day.
1. Drew Barrymore at the Ever After Gala 1998.
To me, this is the greatest dress of all time. I think that it is so incredibly gorgeous and unique. I love how the fabric flows and all the different colors used within it. I think that the shape is just stunning and if I could, I would buy this dress in a heartbeat. It has an almost cathedral-like design on it which feels very one of a kind. This dress is my ultimate favorite and I love everything about it.