Thanks for this interesting topic!
I only have one close friend, the kind you can count on. Several friends have moved. I have some warm friendly acquaintances.
My friend has a lifelong interest in fashion, style. She would get most of her information about current fashion from television, either tv shopping channels or news anchors or a soap opera. No internet. She has an apple build and favors slim pants that she likes to purchase low waisted because of her belly. Doesn't wear skirts because of same reason.
Does wear dresses, usually a loose skimming fit. Is sensitive about her arms so is looking for sleeves or a topper. Whether or not matchy matchy is in style, it always is with her. Everything *has* to match.
If she has shoes she likes, and they have to be feminine, she will hold on to them for years before wearing, until she turns up a sufficiently matching bag. She wears a baguette style bag, hand held, because she had back surgery and was instructed never to wear a shoulder bag. We are roughly the same short height and sometimes similar in weight. But she can pull off things, like capes, that I utterly fail with. They somehow hang beautifully on her while I look like I'm flailing around inside a collapsed pup tent.
I have a friend who is a practicing attorney in her 80s. She is tall and sturdy but often favors lacy boho tops and they work on her as not appearing too-too. For dressier occasions, she might favor a sleek black skirt or pantsuit with a hint of cleavage. So, sexy in her 80s. Does not in any way look 80, though.
Have a friend with wide hips, big belly, big bust. She often favors oversize wide shapeless crop pants and we say to her in the thrift store dressing room, "But how many more do you really need?" and she puts them back. She likes very romantic things like wide white eyelet skirts but ultimately decides they don't really like her and she returns them. When she wears sleeker, more skimming clothes with less kitschy elements to the design, (I think) she looks her best. She can do casual really well, even when her heart's not in it.
Had a friend, since moved and been ill, a tall retired woman who is a preacher. Very beautiful face with a dimpled smile. She dresses modestly according to her lights, so no pants and only longer skirts.
Always a hat. Jackets. Scarves. So she's always "dressed up". The thing is, she has this amazing creamy dark cinnamon skin tone and I have never seen a color she couldn't wear. And many pieces that might look garish on someone else, fall right into line for her.
I had a friend, moved away, who is an extreme pear shape and while she might dress up, I had never had the occasion to see it, and she is very come-as-you-are. Wore pants/jeans, sweatshirt, belt bag wherever she went, whatever civic meetings she might attend and even speak at, presumably to her job. She was always appearing self-assured so that everyone else verged on looking overdressed.
A neighborhood friend has a style I really admire but cannot pull off.
Tallish, leanish, very casual masculine style clothes, often including a trilby hat. Looks feminine in them, anyway. But the same women likes to go out to the casinos and buys and wears ultra glamourous, even sequined, bombshell dresses and looks terrific in those, too.