Should I feel bad that I see nothing wrong with your look Suz, in fact I think I could duplicate it tomorrow and feel good.

Naw, I say, Viv! It's a personality thing, IMO. Not to get all serious, but this is one of the things that led me to YLF. I was trying to get rid of dissonance in my dress v. my true nature. People feel it. You feel them feeling it...

Rachylou is right, Vivian. (And thanks for weighing in, Rachy). It's absolutely a personality thing. Nothing *wrong* with the outfit, per se. Just not right for *me.* And I needed to figure out why. I have a much clearer sense of that now.

I haven't read all the responses Suz but the outfit looks fine just not you. White jeans or kick flares might work. I am not the biggest fan of Bermuda shorts so there is that.
I am clueless about Chicos. I will have to check it out so I am up to speed. I just walk by the store and have never gone in.

Sears Catalog! LMAO!!! That analogy is too funny, it would put a damper on any outfit and make anyone confidently stepping out of the house suddenly feel like crawling back in as quickly as possible.

I think what you are expressing is that now you feel your new hair is demanding more drama in your outfits. Without at least a hint of it, you associate it to images we Canadians have all been traumatized with since childhood: cheap, coarse, non-sexual ready-made outfits for different times of life, outfits that scream "I have given up"...

Of course, and I want to insist, the present outfit shown here is NOTHING like that. You look fresh, put together, very jolie. Your footwear brings it all together IMO. But I do understand what you mean and that's why I suggest you inject more dramatic pieces/accessories. After studying the present pic, I have determined it is the combination sandals-Bermuda shorts that may be the real offender for you. Why not trying to wear the same thing, but swapping the Bermudas for a long straight cotton skirt ?

BTW we have similar proportions, and this year I tried my white Bermuda shorts and 2 min later back in the storage bin they went. I just felt they were not me this year, and it may have also to do with the present boho trend dominating now. My preppyish golfy Bermudas were just clashing with the silhouette I favor these days.

Didn't read any comment, but think if any fail at all(???)it may be only the shoes. Dunno, perhaps straps are too wide for that bright white...a bit looking like old lady's comfort shoes for this outfit....otherwise it is a great modern classic, what's wrong with it???:-(

Great post! Thanks for posting Suz and garnering such a great variety of input that indeed teaches us all.

FWIW I also sometimes wear an outfit that makes me feel like you indicated this one made you feel. I probably would retire the shorts and go for white denim shorts as a replacement -- if you wanted white shorts. Or maybe wear these another way - with a long asymmetric tunic over them maybe? I just got a pair of white denim jeans but they feel too heavy for our summer so I'm not sure I'm going to keep them. But the other thing about them is that they somehow feel too preppy or old school. Maybe I need distressed white denim, or a tighter fit (or both) - I tried white kick crop flares but couldn't get them off my body fast enough.

I also have the navy bag (I think it's the same one or very similar) and though I love it's size, usefulness, etc., I do sometimes feel I have to "work" it better into my outfits because it is SO classic and I like a little bit of RATE.

I don't think there's anything wrong with the outfit, although I agree metallic sandals might look a little spunkier. Having gone through similar crises of confidence since my hair has been getting greyer, I think your problem isn't so much the outfit as your hair, and getting used to it. I still have a moment of "who IS that?" when I first look in the mirror in the morning, but I'm mostly used to it now and I don't see that disconnect between my hair and clothes the way I did last year. I think this is about the time when women who are transitioning to grey hit the hair dye, and I encourage you to wait it out. As the ads say, it gets better.

Holy cow! I go away for two weeks and you cut off all your hair and... go gray? Wow!!

I don't see one single thing wrong with this outfit. I would wear it!

Wow, this has been a long thread!! I wonder what the comments would have been if the title was WIW = not Outfit Fail.....

Suz - you look wonderful and fit and healthy and chic:)

First impression, I like it, as a clean, polished summery outfit. Yet, if it doesn't give you that "feel good" emotion, then the suggestions made here are helpful.

I know what you mean about "a look" that just doesn't feel like "you" and you want to take off the the outfit, immediately, and figure it out. I don't wear bermudas or shorts, of any kind, except on a particularly hot day, I have one pair, some longer just-above-the knees denim shorts, which I like for their casual vibe.

Honestly, Suz, I applaud you for always pushing the envelope in all directions.