The Historical Moment That Made Pairing Dresses With Sneakers Actually Cool

Do you remember the music video for Lily Allen's "Smile" from 2006? I can actually recall watching it for the first time thinking "Oh my God, the audacity of her wearing those pretty dresses with *gasp* TRAINERS." 

If you're not old enough to know this, it's important to note that back then, the pairing of dainty dresses with trainers or sneakers just wasn't done. A pairing that you see on the daily now without batting an eye was pretty much considered groundbreaking at that time.

But even in my disbelief (on top of my 20-year-old self's belief that pretty dresses go only with darling delicate sweet shoes), I can't forget the fascination I had with each head-to-toe outfit Lily had on in "Smile" and wanting to repeatedly watch the music video just to study what she wore. 

The long pale yellow dress — with trainers! The chunky heart-shaped gold earrings. The (super duper cool) layered gold necklaces. That sweet, sweet bright pink midi dress — with trainers!

PS: Full disclosure, I started layering gold-plated necklaces  three at most  in 2006. Coincidence? I think not.

Google it now and you can see articles talking about how that video is seen as iconic now. It was a historical moment and Lily Allen became a trailblazer in the style department afterwards, paving the way for women and girls everywhere to chuck their ballet flats out of the way for the more favourable and comfortable trainers and sneakers, worn with their daintiest dresses.
Shoes that were previously seen as exclusively "sporty" or for men's casual wear only became a staple in all fashion girls' closets.

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I have an extreme love for matching my dresses and sneakers which is evident from the many outfit posts in my blog here, and I probably have Lily Allen (and her stylist or stylists, if she even had any) to thank for it. So, thank you, Lily Allen.

To accompany today's posts, here are a bunch of pics of me in a dainty daisy print ruffle blue dress paired with baby blue sneakers — of course.

Check out my other dress + sneakers pairings on the blog:

Thank you for reading this post, loads of love ❤❤ until my next one!


  1. Hi stylish woman! You look amazing as always. Talking about Lily Ellen, well, I remember that song Smile being THE song that was on repeat everywhere. Totally was addictive. Didn't know much about her style and how she introduced the pairing of sneakers and pretty dresses into the fashion sphere. Thanks for sharing this interesting tidbit! You look absolutely chic in your long dress and sneakers. The popping bag truly brought the look together. Such a happy look. I love it so much! Hope you're well and here's wishing you a fab week ahead <3

    1. I do wonder if Lily Allen (or her team) was inspired by someone else's fashion breakthrough but for me personally that was the IT pop culture moment of dress + sneakers to me!


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Hi, I'm Liyana

I'm a style & lifestyle blogger based in sunny (and ever humid) Malaysia. On The Good Weekender, you can find typed journals of my evolving modest personal style, travel adventures, skincare/beauty updates, home decor things, and stories of other bits and pieces of my everyday life. I hope you'll enjoy flipping through these pages of my virtual book!