RomCom Fashion: Dressing Like Characters from the 2000s

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Generation X grew up during a time when fashion started with an amazing 70s vibe that revolved around all thing fringe. Unfortunately, fashion moved into a dayglo and leg warmer nightmare. Honestly, the 90s were a blur of slip dresses and frigging logos splashed across every person’s chest. And then 2000 hit, and there’s no better way to showcase the fashion from the early 2000s than the RomComs that arrived year-after-year-after-year. Yep, RomCom fashion, it’s here and it doesn’t seem to be going away anytime soon.

romcom fashion

2000s RomCom Fashion

Personally, I love RomComs. I can’t get enough of them. I loved how many came out throughout the early 2000s. On days I want to be a couch potato, I channel surf in hopes of finding all the early 2000 RomComs, and listen, if I can’t find a kick-ass 80s movie starring a Brat Packer, or one directed by John Hughes, then an early 2000s RomCom movie it is! If I had to rewind the tape and live in the early 2000s again, I wouldn’t mind dressing like characters from some of my favorite RomComs.

Need a little inspiration? No problem. I found a few items for each movie below to help get your imagination going!

13 Going on 30 (2004)

Whenever people think about Jenna Rink,  the multi-colored cut out dress she wears for her Thriller dance pops into their minds. Not me! My favorite part was when she kicked that jerk in the nuts in her office, so the outfit she’s wearing screams JENNA RINK in my mind.

13 going on 30 jenna rink

Obviously you can’t match it exactly, but the smart part about recreating her outfit from this scene: khaki pants. Ladies, every good wardrobe should include at least one pair of amazing green khaki slacks. Or, if you can pull it off, cargo pants, because POCKETS.

Inspiration pieces:

Have fun with it! And always remember how great it must have felt to let that married loser have it!

The Holiday (2006)

Who doesn’t remember all the comfy casual clothes Cameron Diaz sported after arriving in England for her holiday house swap? Since I hate pink, I loved seeing her in some pastel purples!

the holiday amanda woods

Inspiration pieces:

Knocked Up (2007)

One night stand ends up in a pregnancy…. a tale as old as time, but definitely told in a funny AF way. I mean, Paul Rudd’s in the movie and though he steals the show, Katherine Heigl’s wardrobe was a close second in popularity to Rudd in my book!

knocked up allison scott


Inspiration pieces:

The Proposal (2009)

More often than not, when people hear Margaret Tate the black skirt suit pops into their minds. For me, it’s the bathrobe and boots as she saves poor little Kevin from a bird of prey!

the proposal margaret tate

Inspiration pieces:

27 Dresses (2009)

Aside from the awful bridesmaid dresses the main character had to wear, she also had a fairly beautiful daily wardrobe.

27 dresses jane nichols

Inspiration pieces:

PS I Love You (2007)

The ultimate love story inspired one of my favorite movie wardrobes…. and my favorite shows off a great long jacket and killer black boots!

ps i love you holly

Inspiration pieces:

The Wedding Date (2005)

When you Google “red dress from The Wedding Date” the dress I love doesn’t come up. The dress that shows up: the one Amy Adams wears in the scene her sister learns about her sister’s affair with her ex-fiance. However, the one Debra Messing wears when she arrives home to England is the real show stopper.

the wedding date kat ellis


Inspiration pieces:

Sweet Home Alabama (2002)

What’s not to love about every outfit Melanie wears throughout the movie, as well as the ones she designed, right? Probably the most perfect ensemble she wears that encompasses not just her new fashion design world, but also her Alabama-style, is the wrap heard ’round the world!

sweet home alabama melanie carmichael smooter

Inspiration pieces:

Will You Take the Plunge into RomCom Core Fashion?

You don’t have to replicate the exact outfits of your favorite romcoms from the early 2000s! Just the vibe and feel your favorite actresses are giving off in their starring roles. Make sure you’re shopping with the right tools and techniques! Have fun shopping and putting your fashion creations together.

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By | 2023-10-16T17:17:17-04:00 September 27, 2023|Lifestyle|Comments Off on RomCom Fashion: Dressing Like Characters from the 2000s

About the Author:

Staci loves to write, and loves to share her "take" on everything thrown her way. Movies, entertainment, food, fashion, shopping, money, travel and family. There's nothing off limits at NovemberSunflower.com, and Staci's always telling it like it is: good, bad, and all that lies in between!