There are a ton of forum posts on this subject but I'm still confused so thanks in advance.

I've been enjoying adapting to my new style after losing close to 75 pounds. I've switched up my wardrobe as I'm an inverted triangle and simply loving the white jeans on bottom and dark welted top on top. I've bought skinnies and leggings and some nice oversized, fluid tops. Great neutral shoes to match. So far so good.

Lately my work requirements need a bit more dressing up than white jeans. I also have some courtroom appearances to make (witness in a civil trial) where I wanted to make my look more conservative and "grown up." So I got a couple pairs of light weight wool dress trousers. They were both on sale at super cheap prices (like $11 each!) so if I can't make this work, I can donate to Goodwill without guilt. I like them both because they are softer and more fluid, which is a look I'm trying to figure out given that I'm an inverted triangle and want to play with softer fits on the bottom.

Pair one: a dark charcoal gray, bootcut (but not super flared)
Pair two: a lovely light mushroom color, straight leg (rather soft vs my normal skinny or straight leg jean)

both pants touch the ground and break slightly when I am barefoot in them. I don't like high heels and when I cleaned my closet I dumped most of my old kitten heels (they were pointy toe and rather uncomfortable).

So now I have a problem, what shoes to wear with these pants? I've got the tops all settled: very soft fitted cashmere button sweaters, open or closed; as well as two lovely blazers that are very fitted and not too padded in the shoulders, one is navy and one is black and has a little peplum; and very lady like jewelry and accessories. (and if you have ideas there let me know)

Question ONE
What I have now that I think will work--do you agree?

  • Via Spiga Burgundy leather ballet flats with a rounded toe and quilted leather with a very slight heel (not quite as flat as ballets)
  • Black patent leather Tieks ballet flats
  • Cream colored mules with a black low heel but open toe
  • Black Taryn Rose peep toe pumps but only if the heel isn't so high the pant isn't covering my instep
  • Neutral sandal style heel with open toes and stretchy fabric straps
  • NOT loafers, brogues or my converse types unless I'm going for the super casual look. If I could wear any of my lovely neutral, yellow, or black loafers, tell me how.
  • I do have two pairs of boots, a pair of black knee high books with a low heel that I was planning on replacing; and a pair of caramel colored fancy cowboy boots that I figured were also not appropriate/didn't know how to use

Question TWO
I am shopping for two new pairs of shoes this fall. I had planned to buy two pairs of booties/shooties since I had none; one in a neutral suede and one in all black, both with rounded toes. Could either of these work with the pants above, and if so under what circumstances?

If you have other suggestions, please let me know!