10 Romantic Comedies That Shaped My Style

May 05, 2020

If social distancing has taught me anything, is how many movies I can (re)watch in a day.
The hundreds of Rom Coms I’ve been obsessed for the past two decades of my life can confirm that. 

Disney movies weren’t exactly my thing… I knew that the moment I first watched Never Been Kissed and much like Josie, I had never been kissed either. 

I always knew I was determined to speak like the main character everyone loved, but somehow I got stuck wanting to dress like the cool girl everyone hated, she always seemed to have the best taste in fashion. All the Rom-Com-watching truly made me think the two couldn’t coexist within me. Now that we’ve dismantled that lie patriarchy taught us about women, we can go on.

I’ve been rethinking my whole getting dressed strategy. Possibly because of all the chances I missed to get dressed and the times I couldn’t stop myself from thinking I’d look ridiculous if “so and so were to see me”. Rewatching my old favorites gave me a sense of what I wanted to portray when I got dressed to go out again, and that’s when the realization kicked in: I have so many movies that have shaped my style!

1. Sixteen Candles

This 80s classic gave us something to look forward to. I was born in the late ‘90s, but fashion always comes back around and I’m satisfied with the inspiration I can grab from those years before me.

What it taught me: Tops under dresses! Get the haircut! Wear pastel pink more often!

2. Clueless

The peak of the school girl look, preppy fashion never looked so achievable to those not in the far-right of the political spectrum. This film had more to its fashion than it had to its storyline. An iconic film that trascended time purely because of the styling.

What it taught me: Mini skirts and tights will always be in fashion. Sweaters vests and cardigans ARE a favorable wardrobe choice.

3. 27 Dresses

This movie has so many incredible fashion moments, even when the bridesmaid dresses aren’t cute or flattering the impact they had in me is forever engraved in my head. The way they matched the bridesmaid dresses to the cultural aspect of the bride or just her personality… THAT! IS! FASHION! Also the floral top from the scene she’s at the bar, where can I get it? I must admit, this is still my favorite movie so my judgment could be clouded.

What it taught me: What to never allow the bride to dress me in. Slip dresses are the superior sexy clothing item. I should probably get married in a pant-suit.

4. 10 things I hate about you

An iconic moment for the film industry. Heath Ledger aka bad-boy-what-we-can’t-help-but-love wins the prize for Best Loverboy Outfit! And can we talk about how Kat’s style is a foreshadow for today’s fashion? Oh! And the fact that Kat’s best friend wore a renaissance inspired look that didn’t look like she was actually wearing a costume? Styling goals if I’m being asked.

What it taught me: The reason for Paloma Wool’s success lies in Kat’s platforms and 
laidback cool girl cargos and camis. Floral print V-neck tank-top dresses are the ultimate “timeless” piece of clothing. Cardigans, again.

5. Never Been Kissed

We WILL talk about Jessica Alba’s looks all throughout Never Been Kissed. I do love me a good Drew Barrymore rom-com but going back to the point I stated earlier… the cool girl just has what I’m looking for. Even though I’m pretty sure she should’ve had a dress code infraction for most of her looks, the confidence she irradiated was enviable. Her Barbie costume? Put it in the cart! The ridiculously 90’s floral cami? In the cart! And her green bralette top with the paisley skirt? IN! THE! CART!

What it taught me: Never be afraid of a little color. Cool girls look sexy because of their confidence, so own your look! 

6. Miss Congeniality

I hated the fact that we all know Sandra Bullock is undeniably gorgeous, yet we had to accept she needed to “look better”. This movie is another reminder to work on our personality as hard as we can, so we don’t have anybody telling us is that’s not good enough.

What it taught me: Simple bodycon dresses and stilettos always go for the kill, and they specially kill if you are sleep deprived. Pantsuits in women, specially with a turtleneck underneath, are worthy of a place in my table.

7. Bridget Jones’ Diary

We have to dedicate a moment to all the underwear scenes in this movie. I very recently rewatched Bridget Jones’ Diary and suddenly had the realization that undergarments are an essential part of a #WFH outfit. This is mainly why this movie is on the list, the other reason Bridget Jones stays on this list is for her carefully chosen mini-skirt to go to work and the see-through top she wore the next day.

What it taught me:  Contrary to my mother’s belief, see-through tops can be chic. Always ask for a dress code at work, if you don’t have a dress code, jean minis are on top of the mini-skirt hierarchy. Single or not, buy yourself feel good underwear!

8. Legally Blonde

A Rom-Com list is never complete without Reese Witherspoon’s Legally Blonde, specially if we’re talking style. I used to be one of those “I hate pink” girls, but right after seeing Miss Elle rock all sorts of pink shades in a courtroom I successfully got rid of my internalized misogyny.

What it taught me: You’re never too tough for a tie-dye halter top. Courtroom intelligence ≠ lack of style. Matching your look to your pet is the chic way to go.

9. 13 Going On 30

A movie that scared me for life, with the plot but saved me emotionally with the style choices. This movie has best styles of the entire list (second only to Mamma Mia! And Mamma Mia! Here We Go Again). There’s something about how all the outfits in 13 Going on 30 still look so fresh. From the puff sleeve green dress to the corset outfit, these are all looks I would style on myself so I can’t miss the chance to talk to you about them!

What it taught me: Babydoll dresses have a long time coming, and they won’t stop until we’ve all become obsessed. You can pull off cutouts on said babydoll dresses! A Baguette Bag goes well with everything, which is why it’s an investment.

10. Mamma Mia! (& Here We Go Again)

Only an awfully thought article wouldn’t mention Mamma Mia! as one of the Rom Coms that inspired their style, luckily for you that isn’t me. Every single one of Donna’s looks, specially in the second part of the movie “Here We Go Again!” looks like it could be worn for an instagram “aesthetic” post. It’s still relevant, specially now that ‘70s inspired fashion is back and young Donna certainly approves.

What it taught me: Overalls aren’t only for farming. Billowy dresses are a summer essential, specially because they make you look effortless but still in style. WEAR YOUR FLOWERS! Flared denim is timeless.

What are your top 10 Rom–Com Style moments?

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