I got these Rebecca Taylor pants and love the silhouette- looks much sleeker than other trouser styles and especially trousers/blazer which I have to work at to not be frumpy. When I got them, I really wanted to also try a size up and tailor back down as needed, but none available- I watched for a couple of weeks as a few sizes came back in, but not the right one. I almost sent them back but gosh the leg line looks good, really makes me happy, so I am taking a chance and keeping.
There is a matching blazer though may also sell out, but I wasn’t sure about the puff sleeve or how much I’d wear it.

The Dolce Vita boots are funny for me. I saw them on sale locally and thought all my happy boxes are ticked- , gray! Suede! Roomy toe! Tight fit above ankle due to laces! lower heel! Match my gray tights! They are very comfortable.
I figured the laced ankle fit lets me wear them under slimmer pants, and with skirts and tights I don’t get flower- pot leg look and could juxtapose the boot with the more feminine skirts.
THEN I read up a little and looked for some stylings and realized, oh my, did I buy “combat boots”? And “ they” say, don’t wear under trousers, that’s dumb; or with skirts, that’s SO 90’s; or if you’re an older lady.....
So I have already worn these under pants, and with winter “ midi” skirts and with pencil skirts ( all skirts with tights for column of color) and I like all those looks and my feet were very happy.

I was not targeting them as being “ trendy” so that’s not a concern, but where am I, do you think- - am I somewhere out there in geezer- ville with Granny Clampett , or lost in the 90’s, or in the mutton herd, and do I have to be very careful with how they are styled ? ‘ cause I had thought I just wandered into the shoe store and found some fun comfy boots that go with a lot of my stuff, but now I don’t know!

ETA: here are some WIW of boots and then tryons of RT pants, and I am trying the jacket.

1-navy midi skirt w boots, 2 BR skirt + Vince sweater, 3-an Angie pick sparkle trimmed top with an AT skirt that has some shiny in the pattern, so I don't wear to work  The long top is not everyone's cup of tea but I like how the off-navy top works with the colors in the skirt. I have a high tolerance for wearing skirts that don't actually match tights as long as tights + shoes match.

4-5 are the pants tucked in top--I will be a little shy about tucking this type of fit and may default to untucked. I can't wear high boot heels anymore so I'm not able to get the supermodel long legline; showing with a light top to show the pants but could wear a darker color. NOT hemmed yet and hard to keep hems folded up for pics. I think they look better IRL with movement, but maybe I have on blinders. I might want to sew the pockets shut.

6 -is the jacket and also 7, shown with a skirt to help the jacket outline show better. Here are jacket concerns but first, I really like how it looks AND feels --is comfy and not so tight through armholes--and realize I like jackets or pants to have a  more feminine design or I look somehow too plain. This is too big through the chest, if one is observant, so not sure. I did NOT like peaked lapels last year but here I'm really liking these but wondering, hmm, may date quickly. Then, it's almost for my imaginary lifestyle, not because I can't use a suit in my work, but because I don't NEED matched suits and my aspirational suit would be a lighter or brighter color. But the pinstripe makes this not quite so dark. I have NO idea what color they think this is, reviewers noted same, it does not look navy or even very dark navy to me, looks soft black. But need to go outside in bright daylight. 

Comments welcome, warnings, suggestions.