Must admit, not a fan of the first outfit. But not because that look is dated, maybe too much for my own minimalism The second outfit is great and more like you but I agree with you on jeans.

Irina - I can see how this wouldn’t appeal to you , and it’s not really how I want to dress anymore either . However , I still have lots of pieces from a few years of boho/ colour rich shopping . Would I buy it today? No , but I can’t get rid of everything or I’d have nothing to wear - lol! As much as I yearn for a more minimal style , I also wonder whether my appearance really supports it . You know , no strong features nor the personality to make it look authentic . But I’m determined to try! The red bottoms are indeed a problem - I don’t own any cream tops , but the caramel is not a bad idea ……

I wore those red/orange? pants with grey and white. Certain shades of soft blue would be nice too.

I like both outfits, but hey, I was that woman wearing the long cardigan at the mall today. I'll never get rid of some of mine -- no way! Though I do really like Vildy's point about energy moving downward or something...that resonates with me, despite the fact that the stripes are horizontal there. Maybe the energy moving downward is why you wanted to get rid of the earrings, too? I wonder.

My most worn long cardigans are solid reds, maybe that amps up the energy again.

Anyway, I love the shirt as jacket on you and think that type of look is a slam dunk because it is current, in one of your best colours, and it adds structure, similar to what a jacket would do. So there you have it. The shirt also works so well with the sneakers.

I wear a lot of button front shirts in summer (when temps allow). I used to wear them as a third piece over a tank -- haven't done that since probably the 90s but would do it again. In any case, the main reason I wear them is because I love the structure.

Nothing new to add except I love the red wide legs!

Wow this post and thread resonated in lots of ways. First off, I will take a stand and say I do much prefer the second version (with overshirt) to the long cardigan. I did not like the sound of overshirt as third piece (I have a specific association with that) but when I saw the picture I was converted.
Secondly, bear in mind I am not a huge cardigan fan on myself because they tend to flop off my shoulders and are usually too unstructured for my preferences.
Thirdly, I happen to have been giving some thought to looking dated (as a principle) lately. Is it still relevant? I am afraid I am going to say yes in certain contexts - big topic and not the main point here.
Finally, specifically referring to skinny jeans, they are being donated in droves, but still being worn by the mothers of the teenagers that come into the shop. (Ducks, don't shoot the messenger .)

Love outfit in pic 2. Looks more like a shacket or jacket than an over shirt. You sure know how to make an open shirt look stylish.

Nr 2 is great of course-and wearable with many other tops under the shirt-but the longer &striped cardi indeed is dragging out your energy/soul a bit. I think is rather on the color combo (of the whole outfit) which is too yellowy/olivey + the unstructured cardi and not especially and exclusivelly the long cardi's fault. I bet the ones your have for work are black- but a cooler off white (ekru-linen taupe color--NOT harsh bright white and not warm cream white) would very much update the first look itself, too-just in another way then nr 2.

Well, utilitarian vibe and color is my jam. Also love the red pants, instant update. Especially at that length.
The hair seems to suit the more minimal look and direction? Reminds me of the Australian blogger who calls in here occasionally.

Jamie - laughing at the skinny jeans comment ;). I sure hope these aren’t considered skinny or my perception is way off - lol.

This is all very helpful and enlightening - and I thank you all for chiming in here with honesty and constructive criticism.

Both looks are perfectly nice and flattering. I like the color palette of the first. I do hear you on the long cardigan over narrower pants look being a bit dated.

I find it difficult to work with fashion directions that read as too masculine, like the oversized denim jacket, plaid blazer or bomber jacket looks you mention, that seem to be prevailing for the coming months. I suppose that in order to work they require absolutely perfect tailoring in width and length, and also to highlight some particular female feature, something I don’t have access to presently.

However, I think you got it absolutely right with the shirt as third piece. I think it was just drapy enough to work.

I was just doing a closet review / purge yesterday and thinking how tired I am of raw hems and tricky cropped lengths for fall. For summer, they are fine.

For this fall I did buy one pair of baggier jeans with a bit of an ankle taper, but am mainly planning to rely on older items that fit well.

I am a fan of long sweaters on me but agree that the second look is better for you - crisp and confident. I feel sloppy in an unbuttoned shirt but this doesn't look sloppy at all. I guess it goes to show that one look is not for everyone.

Totally feel you about being tired of my wardrobe though. And my problem is I just don't know where to go with it.

I don't think #1 looks dated. However, I think there is too much "fight for attention" going on within this outfit. Broad horizontal colourful stripes might not be the best pattern for you. Here, they try stealing the show, but get hard competition from shimmering top, shimmering sandals and statement earrings. One or two of these elements would probably have been enough.

#2 looks much more cohesive, fab, confident and "you."

A coatigan in olive (or an other calm colour) or in a pattern suited to your proportions may serve you well!

Love your update! Agreeing with The Cat that it's more about #1 feeling Algo, for your more minimal preferences.
I totally relate to "fun till it's not". It happens, at least with me, when I overhaul too much at once. Then the whole lot feels dated all at once a couple years later :/
PS I like the new profile pic!

What Angie said. The first looks summery and the second looks just right for fall. Both outfits look fabulous but you must feel right in them. You have a wonderful sense of style and can do no wrong. I look forward to seeing your evolving styling looks.

I like your update a lot. As others have said, I don't see the first outfit as dated per se, but I can see how it represents a style that you are moving away from. The second outfit has a neater feel, both in terms of the structure and the tonal color palette. It is more of your pared-down vibe that I think you are heading toward. Nice job!

You know, I never gravitated toward the shirt-as-jacket look either for all the reasons you mentioned - but it looks fabulous on you! Making me think i should give it another try.

It's a total a-ha for me about the cardi 'dragging down' instead of lifting up - this is probably the issue with me, combined with the fact that I need structure in my shoulder line, and cardigans do not give me that. Regardless I will continue wearing them because I love them - but maybe pair them with something more structured. Or maybe not, ha.

I vote that you give away the jeans, for the reasons you mentioned - i too never touch jeans during the summer months - as much as I think I will wear them - so keeping jeans that are only good for a small Spring/Fall window doesn't make sense in my climate.

For wide legs, i love them and wear them almost exclusively now, but almost always in drapey fabrications - I find the structured ones make me look stumpy. You don't look stumpy at all in yours - but maybe something to consider.

Had a thought, that have you done the three word thing about your style. Angie has been doing this (not always three words) for a while and it seems to be popular now based on a couple of Youtubers I watch.

Mine are relaxed elegant energetic. I don't know that it's perfect but it's close....

There's a few ways you could go - I think of your style as modern soft polished neutral and you could add in edge or minimalist or something else or swap them around.

I find it helpful when I consider something that I like (on others or online) to help keep me focused.

Late to this thread, but this has been a really interesting discussion. I concur with others that the olive shirt-as-jacket look is amazing on you. And the long cardi just doesn't seem like you. I think you have a pretty well developed sense of where you want to go with your style...trust it.

ROTFL at the “Chico’s lady” comment…

LOVE the second outfit the color really suits you .