Frumpy to me.

This is not a thrown together look; she has pulled her pointy collar over the sweatshirt, pushed up the sleeves of her sweatshirt and folded the cuffs of the dress over the sweatshirt. Lots of attention to detail!

I wonder how much we are influenced by her expression? She looks sad and dejected....what if she were smiling directly at the camera with a hand on her hip? But each pose is only one instant in a day.

For me, I have a poison eye for lettering on sweatshirts. I think I'd like it if the sweatshirt were plain and cropped. I do like the length of the dress; it's unexpected in a young girl.

There is something both gamine and studious about the looks above Jonesy and you are right the attitude ups the style quotient exponentially IMO.

Granted, this is street style pose, so the wearer was probably caught off guard.

Thanks for the visuals, Jonesy! As I mentioned in my comments, I like the concept too. The proportions are critical though - and no slam dunk. I think you have to take the concept of the look person by person and one proportion at a time.

Good examples Jonesy; most of your subjects are smiling!

I really like the socks/oxford combo in your last pic; would love to see that on this girl.

Angie, is this a model? I feel sort of funny participating in a public dissection of a young kid on her way to work.

Diana - I have the same reaction but also don't want to body snark. But even if we assume she is healthy and "it's not her, it's the clothes" that are wrong, I don't think clothes this oversized are "figure flattering" on a very thin woman. So when people say she can get away with this only because she is young and slim.... I really disagree, just my take / POV.

I don't like , either and am trying to think why.. My first impression is that the model is unhealthy looking- I mean did they airbrush her legs? so I wonder how much of a role pose plays-- if she appeared more vibrant and in motion, would I like it better? Then the juxtaposition is too extreme as mentioned, which is interesting to me 'cause I think, how do you tell that? How to push the edge and still look right? So a Jean jacket or cashmere "sweatshirt" I might tolerate , but is that my ultra- conservatism?

Isis, I don't know if she is a model. The outfit was posted on a street style site called "Street Peepers", along with a billion other people who have been photographed on the street because of their outfits.

Here is the link, taken in Milan:

http://streetpeeper.com/fashion/msgm-milano

The scale and proportions are all wrong.

Thanks Angie! I do love street style!

She doesn't look frumpy because she's young, and it's hard to look like an old lady with a face like that.

I still don't like the outfit though, but the shoes are my favourite part.

Frumpy to me. The combo of the shoes and sweatshirt don't seem to work. This takes advance YLF skills to figure out so I will leave my opinion at that. Interesting puzzle to figure out, though.

I think this outfit is fab... maybe frumpy fab, but fab. The platform heels are required IMO.

However, I don't think this outfit will be fab forever. It's a play on current trends.

The sweatshirt frumps up the dress, which would probably still have frump tendencies but could be jazzed up depending on how it was worn.

Not liking the shoes.

Not liking the model's vibe somehow either. Even for a "caught half unawares" shot, she looks very uncomfortable.

she's striving for too much wit

To me it's neither fab nor frumpy, but most of all trendy and fashion-y - and I mean this in a neutral way. (To me trendy is the opposite of frumpy; on the other hand I personally don't like this interpretation of the sweatshirt trend, so I don't really find it fab, either.) How is that for an answer?

Jonesy, even though I'm not generally a fan of the overall big and loose silhouette, I like these other examples much better. Again, I say the details of styling and proportion make all the difference. I feel like a Project Runway judge saying this, but the styling makes this young woman look older -- the too-polished hair, the shoes, and the hemline and sweatshirt lengths are awkward. The bag seems insignificant too -- something a bit bolder/quirkier would make this whole look more intentional.

Late to the party, but I vote frumpy. The components seem too polished for the printed sweatshirt. I like juxtaposition but this just looks off. I think it looks okay on her but I don't think it would translate well to others. I'd like to shorten the dress and swap out the shoes for short, flat boots. Muss up her hair a bit too.

All these replies are so interesting! Makes me think that maybe we need another word beyond "frumpy". To me it seems like this person was "trying too hard" to be trendy, but for various reasons (love the analytic eye, Angie and other posters!) it just doesn't really work and in the end looks awkward. But to me that is not the same as frumpy, which to me implies less caring. Sooo, is there a word for "tries to be fashiony but ends up looking awkward"?

like 35 words for snow

We need more fashion vocabulary.

If this woman in her outfit was walking toward me on the street , I'd think "pretty fab". I love the juxtaposition of her dress. hair and makeup with the sweatshirt. I think she looks gorgeous. Not every article of clothing or outfit need be "body con" as they call it now . To my eye, the proportions work well on her .

I love it but not with that color sweatshirt or the writing. Different color, fab. Doubt I would ever combine these elements but now I will think about it.

It's mildly witty, high/low...

Actually the skirt is not that long: look, it hits just below her knee. Her legs are very long and it gives impression of much longer skirt IMO.
However I am not in love with this look which is not a surprise because I don't like swetshirts in any incarnation. This length of the sweater may go with the same skirt length if the skirt is very tapered but for flared skirt I think the top length should be much shorter, almost waist length - or high-low hem where high portion is above the waist.

i like the concept behind this; but not the execution. the skirt needed to be either longer or shorter. at current length it needs to be more pencil skirt in shape.

I think it needs a few more cues to make it fab...as it is I think the elements aren't really tied together and it looks like she had a great dress planned, ended up freezing and so decided to wing it with the sweatershirt over it, which looks like something you'd sleep in. I think it's because that sweatshirt is the only funky part of an otherwise pretty classic, dressy look. Pulling the collar over it doesn't give enough of a deliberate cue and so it just looks odd to me.

I like the photo of Jonsey's where she's color-cordianted the red with the sweatshirt with her shoes. That is what I'm trying to say - she needs more accessories, maybe? Or maybe just a different color sweatshirt, athough I don't think that's the sole issue here.

I think it's intentionally frumpy, which is a whole style unto itself. I wouldn't wear it, but I like it. I think it's interesting.

That said, I would have made the exact same tweaks Angie suggested.

It could be fab, but this outfit is frumpy, for two reasons IMHO: I don't like her shoe choice and she lacks a confident smile!

Not exactly frumpy--but fashion victim. I agree with many of you that this could work.

I like Jonesy's #1 photo--the proportions of the long sweater over the skirt illustrate the golden mean almost to perfection. And, admittedly, a long sweater is chic-er than a sweatshirt. I wish we could see the shoes in that photo.

I've seen better versions of this look, like the one Jonesy's showed. I like it though.