Astrid, this is a very valuable epiphany! I'm sure it strikes a nerve, a recognition and a reminder for many of us!
"Clothes are there to enhance our self-perceptions, not define them." --- what Michelle so eloquently said! Comfort is a lot more than skin-deep, and not always sweatshirt-shaped!
I'm also with Una --- I *know* I can dress to resemble a bombshell hourglass if I want, because I have done it in the past and received compliments on the look. But it feels less like me than a smock, a tunic, an A-line dress, a slouchy knit top or drapey blouse. YLF, for me, is about finding ways to look like myself, yet pulled together, It's *easy* to pick up white or blue, plain or striped, crisp and stuff-collared button-downs to pair with my jeans or dressy pencil skirt, because that's what womenswear means in most shops --- and it *is* a quick gateway to 'professional-looking'. But then I fuss all day, because I feel self-conscious and/or incomplete somehow. In the past, I've tried to remedy this with adding scarves or jewellery --- but even that can feel fussy at times. It look some doing (and a lot of nudging!) for me to realize I *can* work the button-down and feel like myself --- provided said button-down is (a) in softer fabric (b) colourful or patterned (c) tailored to fit at waist and then flare, rather than being a straight boxy fit a la menswear. In other words, I've brought my general rules in to supersede or overlay the basic mainstream fashion rules.
Done correctly, picking and choosing means no one notices you're ever uncomfortable and thinks you're always stylish. You customize the rules for YOU. I've seen many super-chic women stick to just 2-3 variations of a simple silhouette. Here, there is Meredith who does that a lot, and looks enviably attractive. There's MaryK with her pencil skirt near-uniform that NEVER looks the same day to day. I remember too the *extremely successful* Editor of an international fashion magazine's India edition, who absolutely *turned heads* because she was ALWAYS in a tailored Indian kurta (tunic), churidars or salwars (tight leggings or slouchy pants), a long dupatta (scarf), with her hip-length straight hair a waterfall down her back --- while others around her ran ragged in a different garment each day, trying to look edgier, more with-it, and the very industry she worked in subjected her to immense pressure to dress more experimentally, more 'internationally', less 'traditionally'. You may be still experimenting a little, to find exactly what feels most comfortable, and that's fine. But once you've established your fashion personality 'rules', you'll do SO much better to heed them over the conventional figure flattery.
The figure-flattery 'rules' may be one-size-fits-all --- but we don't *have* to wear it in defiance of our own comfort guidelines! It's one thing to stretch your comfort zone --- keeps us growing and accepting of the new --- but quite another to leave it and cross into entirely foreign territory. I think it'll help if you can figure out what exactly are the *discomfort* factors that brought you to the epiphany --- and what you'd have preferred instead.
Then add them to the bottom of your shopping list for the future, and you're a step ahead!
