Eclectic Joy

Same consignment shop as the EF coat in the other post. I 'd been wanting a year round weight longer black blazer to update an old one but wear them casually. This is a light wool Anne Klein. Is it too tight in the midriff? I don't think I'd ever wear it open though, but am unsure of length and fit. The black is hard to see. Does this deserve a place in my wardrobe or should I keep looking? Does it look modern enough? Please be completely blunt. I'm wondering if I even want a black blazer and need advice.

I went looking for fluid tops and found this EF light weight coat. It's a light black or dark grey. I left it on hold. What do you think? It's a little over $90.

Is this too crazy? It was chilly this morning so a popped a plaid shirt under a plaid sweatshirt. Too much?
Sweatshirt: Target
Shirt: Cosco
Jeans: H&M
Shoes: Cons that should be replaced.
I'm wearing this for home chores and dog walking...if you think that it can be worn in public. Thoughts and suggestions appreciated. This is a very low budget outfit and I can donate some or all of it if you think that best.
The shirt is quite oversized.

I'm showing you an outfit that I was not completely at ease wearing. The silk burgundy and grey jacket feels like the type of plaid garment a woman of my age should be wearing...a bit more dressy than a flannel shirt or sassy pants.
The clutch was found on a visit to a new consignment shop. I like its large size for a daytime clutch and the doggy print lining was a plus. But I wonder if the whole look too urban for me. I did exchange a black studded belt for this more decorative one. What are your thoughts? Do the burgundy jeans and silky top soften this enough? Too matchy? Or is this an ok look?
Top: Puli
Jeans: H&M
Booties: Munro
Clutch: Ted Baker via consignment
Belt: ? Old

Inspired by Angie's blog ensemble this morning, I scoured the closet then remembered the donation bag. This outfit is almost entirely, except for leather jacket and booties, from that bag. Does this work? Should jeans, shirt, and/or shell go back in the bag?
In the past I have mostly worn the silk shirt with my black furry vest, also in the donation bag but it may get another season if still on trend.
The jeans fit well but I've been off boot cuts. Should I reconsider?
The third photo is yesterday's outfit. I've shown this before except with black flats. Do the peep-toe booties work?

I have been saving this inspiration for a cooler day. Today the orange blazer will not get much use but I will carry it just in case.
Silk tee: Trouvé
Jeans: H&M
Belt: old one of DH's
Leopard pumps: Banolino
Blazer: Vince Camuto
I will use a large tan ostrich textured tote from Target to carry purse stuff and class stuff.
Is this too wild? Do I need darker or different makeup? I appreciate your comments and suggestions for improvement.