GREAT question!
I have been a YLF member for 13 months, but I had started my "makeover" before finding YLF, with purchase of my very first premium jeans. Prior to that purchase, i would buy jeans but then rarely wear them, and this was true as far back as I can remember, even in my teens. I just never found them comfortable or flattering, and always felt like a schlumpa-dinka when wearing them.
I discovered YLF through googling - the first link I found was the "smart casual formula" and that revolutionized my wardrobe!
Since joining, I've learned to embrace:
1) cardigans - I did wear twinsets before but YLF taught me to break them up
2) blazers - with jeans and other than worn as part of a suit
3) dressy, silky blouses with interesting details like ruffles - prior, I'd only ever wear shells
4) camis - believe it or not, I only ever wore these to sleep in. It never occurred to me to use them to make a too-low neckline work.
5) low-vamp shoes
6) clamdiggers - gone are all the awkward capri length pants!
7) I only own one single pair of khaki slacks now, and they are dressier ones
8) white denim
9) add white to an outfit (year round)
10) statement necklaces
11) wearing colorful or metallic shoes that don't necessarily match anything else in the outfit
12) the pleasures of a cream handbag and a cracked black patent leather handbag
I'll add to that: confirmation that it's perfectly fashionable to wear less make-up; I had already given up eye shadow and blush years before but it was good to hear Angie give my minimalist routine (moisturizer, a few dabs of foundation, mascara, and colored lip gloss) the thumb's up.
On the pushing the envelope front, if Angie had a quarter for every time I have initially dismissed a certain style for myself, and then turned around and embraced it anyway - or at least managed to pull it off - she'd be rich by now. LOL.
I have tried:
1) pencil skirts - difficult to find, but I'd like to add more
2) boyfriend cardigans - I think this is a fun change for the weekends but not something I would wear all the time
3) belts - another one I don't prefer, but I can pull off occasionally
4) dress over jeans - my husband says this is weird but my DD16 gives the look two big thumbs up
5) Skinnies - this is a keeper!
6) Skinnies tucked into boots - another keeper!
7) yellow (as a bag - a keeper!
8) scarves tied the Angie way - a good work look
9) moto jacket - so far I have learned if I get one of these, it won't be black. It's too tough of a look for me somehow. But something in a softer color will probably work.
10) crisp white collared shirt - I can do this, it's great for work, it looks good but I still find this to be not very comfortable to wear; I'd rather wear a dressy blouse.
11) Vests are here to stay.
12) graphic tee
13) long necklaces
... and as soon as those leggings arrive I'll be trying that look too.