I don't particularly like the look. Part of the problem, for me, is the banded sweatshirt. I could handle the sweatshirt better if it didn't have that banded hem. Different shoes, like booties, might make the outfit work better too.

I really kind of like it, but not for me.

In my opinion she looks too impeccably groomed for the sweatshirt over dress to be a case of "I forgot my coat so I put on this sweater because it was in my gym bag!". She is beautiful, but the sweatshirt-over-dress does nothing for me.

I've seen this look done well and I've liked it, this one isn't doing it for me.

I feel there is a lack of authenticity in this look. I find it very contrived. It's not frumpy on her (it would be on me) but to me its uninteresting. I thought it might have been a Satorialist photo. Don't get me wrong, I like the idea of this outfit but she makes me think of a little girl playing dress ups:)

I have to be honest here and say I think it looks like she's wearing a uniform where she's worn a jumper over the top of the dress to try and disguise it.

Here's blogger and model Hedvig Opshaug wearing the look well.

http://the-northernlight.com/?s=jumpers

My fixes:
- tuck the collar in under the sweatshirt.
- "blouson" the sweatshirt a bit.
- shorten the skirt
- wear pumps in a fun color
- change the hair. Or -- wear a cute beanie.
- stand up straighter and smile like it's the best day of your life

Even with these changes, the look might not work.
If the dress's skirt had a pencil silhouette, the outfit might work much better but I'm assuming that would be hard to alter.

I am woefully late here. Only had my phone with me today and wanted to get a better look at the photos before commenting.

I agree that the word "frumpy" doesn't seem quite right -- it is too intentional a look for it to be frumpy, IMO. But it isn't conventionally flattering, and somehow misses that unconventional flattery that spells "cool." I like Jonesy's other examples much better, particularly #1. But that is not a sweatshirt and the skirt has a different shape. I DO like the loose, voluminous nature of the look. But I don't care for those shoes.

My first thought was she was going to the company picnic and making the best of the required logo sweatshirt. I generally speaking love this look - Jonesy posted great examples. I do not think this particular one particularly works though. The cuffing and collar are too careful and deliberate with for the fun of the look and the shoes hurt me just looking at them.

Don' like it at all. Will now go back and read the other replies.

...late to the party but I agree with most above: it doesn't work in this particular case. The print on the sweatshirt is too much and the heels really don't go with the sweatshirt, despite attempts at juxtaposition. More contrived and awkward than frumpy. Like she is trying too hard to be on trend. I haven't used this word for a long time, but "poser" comes to mind. (I can be mean sometimes, I guess). I like Jonesy's pics better but I am not a personal fan of this style.

Now the outfit in the link that Claudia posted looks so much better to my eye - the short skirt I think makes the difference.

I don't mind being the odd one out. I agree that the outfit's not very flattering, but I do think it looks very cool. The proportions feel funky and fresh to me.

I have the same issues with pose (or lack of it) and expression, but this is expected with true street style photos.

Frumpy. The other photos of similar combination work because the shoes echo a more child-like or 'recession dressing' feel. These shoes take it to looking like trying too hard, not to look like you're trying.
It possibly the still shot effect too. She would look pretty cute dancing in it.
Still vote frumpy though.

I'm not sure I'd go with frumpy to describe this, but I don't like it. I think the dress looks like it is too big, which makes her legs look extremely thin. That kind of shoe bugs me, too, and I definitely don't think this style goes well with a prim little dress like that -- they are far too glamorous, in my view. And I have a poison eye for sweatshirts like that -- if it was more interestingly shaped (maybe a scoop neck? no band at the bottom?) then it might be better. A shorter and/or more close-fitting dress would look better to me. As it is I get the impression of a young girl playing dress-up, but being made to put on a sweatshirt before going out to ride bikes on a chilly day.

Wow - how did I miss this yesterday? Fun discussion I've skimmed over the comments so far, and a lot resonate with me.

The first thought I had was - here's an example of age appropriate dressing - and only the 'youthful' should attempt this look. . . I wouldnt' have thought this look could really work at all except for Jonesy's pics showing variations that DO work.

It's like original pic is a sort of volume on volume with the dress that looks too big (cuz all we can see is the skirt) and the sweatshirt that is purposefully oversized.

My easy fix is shorter skirt to show kneecaps or smaller sweatshirt.

However, if volume on volume is part of the goal, then Jonesy 2nd photo did it better - with it's longer, slouchier sweatshirt, and even longer more narrow skirt.

Mmmm... I'm having a hard time because of her hair and expression. "Frumpy" and "grumpy" are too close for me. And her hair is cute, but not edgy enough to give the look some tension. So I'm going with frumpy, although I can see this being totally adorable if she were just smiling. Makes me wonder if I should smile more in my pics, but then I have to do a million takes because I look so freaking goofy. Aida needs to give a class on smiling mysteriously!

In thinking about this, it's the fact that ,on this particular girl, there is no joy or exuberance. She looks sullen, far too thin and not happy to be expressing herself with this outfit.
MAYBE, it could look fun or ironic or whimsical on another woman, but not on this one.