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20 Best Romantic Movies With Great Fashion

Does that sound like a strange combination to you? I love watching movies, it's a great thing to do with your Valentine. I have seen a LOT of movies, especially older movies and I thought this would be a fun twist on the romantic comedy lineup. These great romances also have great fashion. Here's 25 movies that make a great date night, and if you watch, the actors are so put together.

20. Just Go With It

This isn't my favorite movie, but is humorous and light. Jennifer Aniston has several "makeover" moments and I enjoy seeing everyone react to her transformation from doctor's assistant to bombshell.

19. When Harry Met Sally

Guys, this movie has been around for a long time. For me, it's a classic. "Report to me Sally." I love Billy Crystal and who doesn't love a good Meg Ryan flick? While the outfits are clearly from the 80s, they stand the test of time for their classic appeal. Be sure to watch for the hat that Meg Ryan wears, the wedding dress, the bridesmaid dress and the New Year's Eve dress.

18. Beauty & the Beast- animated

Family movie night. I know pretty much everyone on the planet has watched this movie, but think of all the romance that that yellow ballgown has sparked in little girls throughout the decades. I was super disappointed that they didn't do a better job in the Live Action movie with Belle's hair for this scene. Too simple in my opinion. I mean, they created a super elaborate set but forgot to make her amazing?

17. A close second is Cinderella, animated or live action, they did a great job of transforming her into the beautiful princess (especially in the live action with all those layers of fluffy blue skirt).

16. Casablanca

This is an absolute CLASSIC movie, and if you haven't watched it, you should. This movie is more for the men's fashion. That trench coat and hat on Rick alone have been staples for years. And who doesn't think Humphrey Bogart looks great in that white tuxedo? I'm looking at you Humphrey. I also like the uniforms of the French.

15. Here's another VERY old movie, His Girl Friday. It a super fast talking, who done it movie where the wardrobes don't change much but that striped suit on Rosalind Russell is pretty amazing. Bonus, this one is a free movie on Amazon Prime.

14. Gone With the Wind

You may think you know this movie (and it's a long one) but if you haven't ever really watched it before, you are missing out on true cinematography history- not to mention an iconic movie. Watch for all of Scarlett's dresses, the red one and the green velvet are my particular favorites.

13. Three Katherine Hepburn movies make my list but the one with the best fashion- Bringing Up Baby. The dressing gowns and the satin gown are stunning, not to mention that black bow on her blouse. (The African Queen & The Philadelphia Story are also fabulous and both a must watch.)

12. Titanic

This movie is a little more cliche now than when it first came out. Kate & Leo were quite the sensation when the movie debuted. And the fashion was incredible. Who knew you could look so beautiful and almost drown in a light and flowy gown?

11. Barefoot in the Park

Need a little 60s fix? Try this kitschy little movie featuring a dashing Robert Redford and a young Jane Fonda. Her cute little outfits make me want to take a trip back in time.

10. Funny Face

Whoa, talk about fashion- this movie has a ton of it! If you know me, you know I love Audrey Hepburn and she's adorable in this movie. Honorable mention, Sabrina which is also adorable.

9. Bonnie & Clyde

Not my favorite movie, because I think it's a little strange, but the clothes, wowza the outfits. Love, love, love. Iconic, I'm telling you.

8. Moulin Rouge

Seriously when I first saw Nicole Kidman in this red dress, didn't she take your breathe away like she did mine? Such a fun and wonky movie. Bonus, you can sing along.

7. To Catch A Thief

If you are on to my theme here, you will discover that many of these older movies star Cary Grant. My dad loves Cary Grant and thus, I have seen so many of his movies. Because they really are great movies. And this one is no except. Grace Kelly in all her glory + a romantic location + Cary Grant + jewels = love.

6. Love Story

This book is absolutely amazing and they made a movie as equally as wonderful based on it. Alli McGraw was a fashion icon in the 70s and holy moly, I love, love, LOVE her outfits in this movie. You won't be disappointed by the storyline either.

5. Breakfast at Tiffany's

Well, it's one of my favorite movies of all time and how could I not include it? One Halloween I went as Holly Golightly. Audrey Hepburn is an absolute queen in this movie. And she had just had a baby? I can't believe it. If you haven't seen it, watch it now.

4. How to Lose A Guy In Ten Days

While this is a 2000s movie, no one can tell me that they didn't pay VERY close attention to what Kate Hudson wore. The wardrobe designer did an amazing job. And that yellow satin dress is a STUNNER.

3. Hitch

Again, another simple movie with very careful attention to detail. I love watching movies like this that are as entertaining to the eye as they are with the storyline. For modern fashion, this is a win.

2. Moonstruck

Another older movie that is an absolute classic. Cher in all her 80s glory. The big hair, the attitude, the dress that about gives Nicolas Cage a heart attack. This movie makes me think I am for sure part Italian. Honorable mention, if you haven't seen Mask with Cher, you must watch. But maybe not for Valentine's. She's amazing in it. (Bonus, it includes Sam Elliott- love him.)

1. Pretty Woman

While this movie has been around and is almost as cliche as Titanic, but it is a fashion and romance classic. Every woman wants to wear that red dress and diamonds and get flown to the opera. And that black cocktail dress, a winner yet today. It's hard to believe how old this movie is and yet, her dresses could be worn today.

I hope this list gives you some inspiration for Valentine's Day. Here's a little graphic for quick reference. Let me know which are your favorites!


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