I like the skirt (including length) and the boots. I even like the opaque tights although sheer would probably be better. I think it’s the sweater that’s the problem. Very interesting what Diana said.

Also, to my eye the bulky scarf worn with the oversized sweater makes the look a bit top heavy. (Although it’s a great colour and I like it with the coat.) I would ditch the scarf (except with the coat) and try substituting a long pendant with no tuck or a short chunky pendant with a semi tuck (as in pic 4). I think the overall look would be sleeker.

Well, let me be the one who sees it differently
I think that the sweater was intended to be slouchy like on the model. Yours, I think, is a bit small. I see it as juxtaposition between oversized sweater and a classic style skirt.
I would soak the sweater in warm water with a bit of hair conditioner, stretch it lightly width wise and dry flat. But is is me, I like oversized

Irina - I wondered about that too. But I am such a completely different body type than the model - I have a bulky chest (especially in profile) and am quite short waisted - which means I probably shouldn't be wearing oversize sweaters at all and that fit is hard to assess.

Brooklyn - yes to wearing a less bulky scarf. I didn't keep it on throughout the day . And I'm taking notes on your jewellery proportion ideas. Thank you for that.

Since everyone else has solved your bottom half:

Can you wear a tonal belt over the sweater to blouse it up, make it shorter (maybe even high/low) and give it structure? I actually love the outfit—you are almost there!

Lisa - first you would look gorgeous in a paper bag. Just sayin'!! I love the color of the sweater on you and the scarf. Love the total with the coat for all the reasons mentions. BTW I love the coat on you. The sweater I agree is too big and the front seems shorter than the back. I do like it with the faux tuck. I have several EF sweaters that are intentionally oversized. The thing that makes them work is the side is split on the seam. This allows the extra volume to drape more gracefully. I know sweaters are hard to alter, but is there a sway to slit and finish the side seams a couple of inches up? Maybe 3? Not so high you'll flash skin (although I always wear a cami under so I have higher slits). Otherwise the faux tuck does work but I've started consciously looking for split seams on oversize sweaters on that length. I just donated 2 for exactly the same reason of styling (but I did the faux tuck to make them work) I like the boots very much, but in this outfit I think I would have worn a suede shootie pointy toe. But I thought they still worked but it's a little more my look.

Lisa, I know what you are saying - I’m short waisted with a bust that is a little bit too big for my frame. Most of EF cropped tops do not work for me for the reason of the side view when a top is sticking out too much. May be this particular sweater needs to be not only oversized but also longer. If your DH is taller and 2 sizes bigger than you, try some of his sweaters with the skirt to get the idea: should the top be oversized or slim fitting. Well, it is an outfit lab, right?
Oh, forgot to mention, may be you will find it useful - I like oversized tops but try to avoid one big blob on top. I look for tops with slim fitted sleeves. Sometimes, I intentionally shrink sleeves or alter them

gryffin - glad you chimed in. I can't really do a pointy toe anymore, unfortunately, and if I could, I'd do it in a heartbeat. I actually have a pair of pointy toe shooties that now go unworn. Maybe for a dressier /sit-down occasion, but not for everyday. The sweater is a rounded high-low shape, which does make it really tough to tuck in . The whole thing is a miss. I'll be looking for a lighterweight, more flattering top to pair with this skirt! What would you do for hosiery here?

Interesting thread - I agree with most of what has been said. I added a sweater last year that I love the colour of yet when I have seen myself in photos I felt very unhappy. I think in reality they look better than a photo though.

I love the coat scarf combo and can see that with the sweater and jeans and maybe a lighter boot come early spring.

Another thing to consider if it doesn’t drive you nuts is to layer fishnets over sheer stockings — not that I’ve ever tried it myself since I live in California and not Canada.

Lisa - I actually like the black tights. Damn girl you have very shapely graceful calves. I do think the high shaft on the booties does not showcase them as well as a lower vamp would. Agree black or nude sheers would work well. I high suede boot very fitted to the calf also be nice and keep those legs warm!

I think it’s cute. My personal opinion is that some sheer tights (black) or with a polka dot embossed into them would be ideal. To my eye the sweater and skirt are fine :).
Just throwing my two cents in.

Love the blush colors on you and your make up is fabulous. I would wear booties that are plainer, for my taste the boots look a little clunky and busy for the skirt. The tights as others have said the tights could be more sheer. The skirt is cute, can you wear with a slip to avoid static cling? I love skirts but find them terribly difficult to style with tops and still look flattering.
As an aside I just bought a cashmere sweater from H and M last week and guess what - it's pilling !

I haven’t had a chance to read the responses, but wanted to comment.

One, you look STUNNING in that delicious pink scarf - it looks gorgeous with your lip color!

Two, I don’t see the “big mess” that you see, but I have felt that frustration. Don’t toss out the whole lot just yet! When you have time, try the skirt (and sweater) with other pieces and see how you feel.

I don’t have time to read all of the comments before I head out the door this morning...

Those blush colors are divine on you!

Is it possible that part of the dilemma is that the black booties + nude hose work on the model because she’s bookending the boots with her hair, and the nude hosiery with the light sweater?

I ask because it took me several years to realize that dark shoes only really make me happy if I either “bookend” my winter-white legs with something, like a lighter top (or matching winter-white forearms and hands) or have darker hosiery bookending a dark top / more covered arms.

Also, I wonder if all those heavy textiles aren’t muting your delicate features and form. I think Angie is spot on about some sheer hosiery when it warms up.

Honest first thought was, what the heck is she talking about? I really like this. I think Bijou nailed it - the jacket adds just the right amount of structure to make it feel really polished.

You had very good intentions in your orginal look and I think it actually works for you. I can't wear oversized sweaters because it just adds the look of more weight on me. I can still see your lovely figure with the oversized sweater. I think your skirt is a definite "keeper". You can get a lot of wears out of it. That being said, I think the sweater would work with something more fitted such as tight jeans or a pencil skirt. ( I loved the coat, scarf and booties too--I'm just fixated on that cute skirt). I think your outfit would look more streamlined with a more fitted top (sweater, shirt, fitted blazer) It looks like the waist is elastisized. You could tuck in your top, add a belt or leave as is since it will show off your small waist.

Diana has said it all so well, I stay away of these kinds of "no proper shoulder seamed" sweaters like plague. But the color way and items are all gorgeous!(Hair, too:-)) Is the model wearing a sock boot or just socks with some boots? No matter what is, you can emulate it , too- but you are blonde and fair so the thing is you have to disrupt all black on legs with showing some skin (or wearing sheers). That will surely also help a lot for achieving the same aesthetic.

Lisa - I was just cleaning up my finds. I wanted to throw this out for you or something of this type. This bootie is woven, it's very soft and stretchy, with a very low heel. So it does have a pointy toe but stretch. It's extremely graceful on. I used to have a similar pair from gentle souls that I wore into the ground. I actually bought a pair and a spare. If you read the reviews I'm not the only one. I wear with orthotics but you could even put in a cushioned liner to reduce the heel and for added comfort. It's only 1.5 and feels low because it's very well balanced keeping weight right above the heel not pushed forward into the toe. EF usually runs small. I'm almost always a 7M. Usually in EF 7.5M. In this I need my regular size, the 1/2 size up was too long, comfy but too long. Just a thought. Zappos has them on sale.

I think you're being too hard on yourself.
I like the skirt, tights and boots! The color of the sweater is really pretty on you too. I think maybe the problem comes in that the sweater was just a bit too baggy or bulky w/the skirt.
Maybe if the sweater was a more streamlined type in that shade, it may have worked a bit better. Ok, so maybe not the best, but hardly a fail.

gryffin - these look interesting - and even moreso upon your recommendation . I don't think Zappos ships to Canada, sadly, but my size is sold out anyways (at both EF and Z), thus dodging a bullet But I'll keep my eyes open for them !Thanks!

Hi Lisa - long time no 'see'!

I actually love the colours in this outfit for you, and I like the skirt a lot, but I think Diana hit upon the problem exactly (at least it's the same one I have!) These slouchy sweaters with dropped shoulders always make outfits look more casual and 'messy', a bit. A set-in shoulder gives a stronger shoulder line, which gives more structure to the look as a whole. I am a pear shape with small, rounded shoulders, so i have noticed this particularly on me.

Ok, you are too hard on yourself, agree that shoulders make or break a silhouette, must leave now to buy pink lipstick - any recs?