Just got back from a completely unsuccessful mall shopping trip. (I had some coupons that expired today). I can tell you that there are certainly many, many styles of clothes I can no longer wear, because of the "gravity" issue.
Top on that list is anything that is too strappy, like halter tops or camisoles that are meant to be shown or anything with spaghetti straps. There were many such tops at AT today - gearing up for the special occasion season.
I also stay away from anything that's too clingy, because the body isn't what it used to be and I've got odd lumps here and there. I need clothes that skim away from my trouble zones, and clothes with a lot more structure than I used to be able to get away with. I actually think I look better - slimmer, trimmer and younger - in fall/winter clothes, because I can layer to add structure, and the clothes tend to have more structure than summer clothes.
Gravity aside, age has done a number on my chest and neck. My face is still fairly wrinkle free, but my neck and chest really show my age. This is because while I would religiously wear sunscreen on my face since my 20s, I woudn't religiously wear it on my neck and chest - because I'd worry it would get on my clothes. And because I have a short neck and I'm hourglassy, I look much better in v-necks or scoop necks so I've spent my life not covering up that skin. And it is showing more and more - no matter how much expensive anti-aging cream I slather on each night and morning.
That presents quite a quandary.... in past year or so, I've been drawn more and more towards tops that provide more coverage, even if this isn't supposedly the best style for my body type. I also want statement necklaces - I used to think this would draw attention to the skin on my neck and chest, but I'm learning it does the opposite. you see the necklace, not the aging skin. I do like ruffly necklines for same reason - frames the face, and draws attention away from aging skin.
As for style of clothing, I do understand what you mean by "ingenue." Though not necessarily with that top from WHBM you posted... I'd have to see it in person. I know it would not work for me, because it would accentuate tummy bulges. But, if that's not your issue, I could imagine layering a jacket or cardi over it, and that might give a different look altogether. I think the pleats are quite lovely and sophisticated.
But basically I spent my first 40 years trying to look my age - dressing more mature and conservative and never ever wearing jeans - because I'm so short and have a baby face. Now that I'm over 40, and have teenagers, I definetly don't want to look like my teens! But there was also that weird knee-jerk, "oh I want to look younger than 40 - time is rushing by way too fast" feeling going on three years ago when I arrived at the big 4-0. I'm getting over that concern and actually quite looking forward to my 50s now. The secret they don't tell you is that once you hit 40, it just gets better and better - people are happier and more satisfied with life, the older they get.
As for clothes, I guess for me I am thinking more and more it is about quality and fit - that's what gives the polish and makes me feel polished. I still throw in an H&M or other inexpensive piece here and there, but I'm more and more appreciating that higher quality fabrics, clothing, shoes, purses (yes, more expensive brands - though I still have my limit!) gives me that look of "she's in her 40s, sophisticated, polished, successful. She's arrived."
This is pretty evident lately when I make my rare appearances in the office. I'm the second oldest person on my team here (the oldest is turning 50 soon - and boy does she look fabulous!!). But most of my female coworkers are in their mid-to-late 30s, and in the stage with young children at home. I do not want to dress like them. I want to dress like someone who is in her 40s. I want people to look at me and think, "wow she's got her sh*t together.... and she must be very successful...." I also want to give the impression: "she's comfortable in her own skin, has arrived at a place where she knows what looks good on her and expresses her unique personality.... and she makes 40s look like an age that is not to be dreaded!"
As for that last bit... well, I have a baby face, and I'm very short. I have learned to gracefully accept this fact, and not fight it so much. So yes I will wear playful clothes and incorporate youthful touches here and there. It's not about trying too hard to look younger than I am... it's about accepting the fact no matter what I do, I'm going to look young anyway!
Does any of that make sense?