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Dress Over Jeans: Homeless or Hip?

My neighbor recently visited Seattle and we were chatting at the pool yesterday about how much we love the city (I'm headed there the end of this month in fact - can't wait!). She said she saw a lot of little girls with dresses and jeans and that it seemed to be a trend there and that women were doing it too.

I think this is something I would like - a little funky, a little hippie - and could wear to work on Fridays, but not sure this part of the South is ready for it. And if you didn't do it right, you could certainly be confused for a homeless person.

For sure if I had a little girl I would totally dress her in this trend. What do you think? Confusing or cute? Homeless or hip? Childish or cool?



  1. i think its cute, but i think it has to be with the right dress... gwen looks like a bag lady... but j. love is so cute!

  2. I love the look - with the right dress of course and properly proportioned jeans, of course!

  3. I think it looks best with a shirt dress, and slimmer cut jeans.

  4. lots of ways for it to fo wrong, but pretty cute when done correctly!! It would have to be in the middle of winter here though, too hot!

  5. Guess I am a little out of style.... I find the whole look a little weird. Think I will stick with jeans and tops.

  6. I think as long as it's a more fitted look it can be totally cute!

  7. Personally, it's a no for me. I just don't care for that look. The girl in the two photos who's a non-celebrity (is she the one who has that clothing blog?) looks pretty cute but then it looks more like a long shirt and not a dress.

    I think JLH looks like an idiot with that outfit on. The jeans look cute, the dress loos cute but together, not cute. JMO of course.

  8. Just found your blog and speaking as a "Bama girl",I agree everyone should have a southern accent:)

    I dress my twins in jeans and dresses sometimes and think it's adorable but I don't see myself in them anytime soon.

  9. I did it in college quite often - usually with a cute, sleeveless LBD that had gotten too short with jeans... it was perfect for tailgating as the weather cooled off!

  10. the first pictures are cute! i say give it a try once and see how it goes! :)

  11. From a southern girl...Love it and cute blog!

  12. Completely agree that it has to be the right dress. Otherwise it's a bust. But with the right dress...I think it's fun!

  13. I bought a dress to wear over black pants, but DH says it needs to be hemmed because it's too long to wear as is. Now if I ever get to hemming it, I'm gonna try it!

  14. I think Jennifer Love Hewitt's outfit is adorable! I say try it!!

  15. I think it is cute if done with the right dress and right shoes....I agree that Gwen's dress choice is less than chic and the shoes are not a great look for the completion of the ensemble!
    A little girl in this outfit would be darling!

  16. I definitely am digging the dress over the jeans. I've only pulled it off once *and got looked at funny* but I personally think it's super adorable!

  17. I think the look is so cute, but I don't think I could pull this off!

  18. It has to be done right. A cute shirt dress and dark bootcut slimming jeans. I like this look. But, it is FAR to hot to do this until fall.

  19. This was popular 10 years ago in San Fran. Since I did it then, I think I will skip it this time around.

  20. I am absolutely enamored and obsessed with this look (which is how I stumbled upon this blog.)


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