I really like the first outfit. It's very cool; white sneakers are a great touch. And no I don't think you're too old to wear a skirted legging.
As far as shredded denim, somehow the white works. "Vanitas". That art history descriptor for those perfect floral still lifes with dead bugs and skulls for Dutch paintings to show the temporal nature of life. Ok that was probably a bit way overthought. Hope you get what I'm trying to say.

Anna - see , yes, that type of art is among my favourite: bugs and skulls and flowers. I don't know the term Vanitas, but I'll be googling it shortly

Angie - I know, I know, I need to get that closet cleaned out again. I really don't want to do it - to try on things that are going to be tight now - it's too depressing. I hate that I sounded whiny - and it's not because I don't know how to dress or what to wear, it's more about not having the things in my closet that I DO want to wear. I can not seem to find work clothes that I like , so I buy the same grey sleeveless tunics/long tanks, white t-shirts, and jeans every time I go shopping because I cant' find anything else to buy. I used to blame it on having gained so much weight , and that is true, but I wonder if it's also because I'm at an age where I can't figure out where I fit in stylistically.....clothes appear too young, or too old and nothing out there seems to represent me or how I want to look.

And friends, thanks again for your comments: a drapier top with the leggings would be a good idea, most definitely. I have other skirted leggings with the skirt being far, far less body con, and those are almost a different breed. I think I may relegate these to walking and working out, or for casual wear with a longer, drapey top. They weren't expensive so I don't mind if they are a once-in-awhile thing.

I do apologize for sounding whiny and insecure - there is NOTHING worse than listening to someone carrying on about themselves. When I talk about not "feeling it" with my work clothes, I'm talking about not knowing what to wear, and not reaching for those things I do have. I think I have a handle on how to dress the body I do have, I just can't find more than the same 3 pieces over and over again : blazer, t and jeans or black pants. I know those flatter, and everything else holds little appeal. Might be time to back away from fashion for awhile and not worry about it . Too much thinking about it never helps me - it only frustrates me.

Firstly, I relate with the trouble dressing, and the sea of tops --- I attribute part of my issue to being in the middle of a huge life/work transition, but it's definitely disorienting.

I love the way you've created two fab outfits by going back to watch you best -- create minimal outfits with equal parts classic and edge. And the little details -- the leather band and the orange mani, set it off to perfection.

The second outfit is a favorite of mine --- the distressing doesn't seem OTT here, and I love the way the cold shoulder draws attention to your face.

I also vote for an edit -- I think a big holding zone is maybe called for. You might find items returning to your closet over time!

Lisa, you have the sophisticated look mastered, even on weekends. Many of us admire your style. There is nothing wrong with blazers, tee and jeans or black pants, especially with your great footwear collection. It is a uniform that you can tweek endlessly.

Now, your cold shoulders top is perfection, it is so hard to find a small opening on the shoulders here. As always YLF- love the skirted legging's outfit, too:-).

Oh my gosh, with your glass on you look like a younger version of Jamie Lee Curtis. WOW.

I find it amazing that you find it hard to get dressed some days, because seriously, every outfit you post is fabulous. Really. But I hear you... it's very depressing to still have that "I have nothing to wear" feeling after spending lots, and having a fairly big closet. I do think it happens to all of us... be it the weather, how we're feeling that day, if we've gained or lost weight, a variety of factors.

Now about these outfits specifically, of course I love them. For one, we are bracelet sisters. And black white and silver is pretty much my fall back, so what's not to love? I think this butt vest looks great on you, and I like how you've made it both sporty and pulled together at the same time. A goal of mine, as I do love the comfort of gear... I think this amount of distressing in the jeans is so you, that it's not about trendy. It's you.

Thanks Elizabeth - you'll notice I don't post outfit pics very often and when I do, I'm usually in jeans It takes that long to find something photo-worthy - lol. Part of the dread comes from not having what I actually need in my closet. Like many of us, I buy things I like and know will work for me and don't always need to be tried on , and thus repeat the same thing over and over again - to the point where I have 10 black tank tops and 10 grey ones. And one pair of pants . Lol. I don't do well shopping for things that are trickier to fit because , well, it's disheartening and quite frankly I hate trying on clothes. And I just do not see what I like out there at retail! Anyways - thanks for the comments - I didn't know you had the Nickel & Suede stuff too. I love it!

Adore both outfits and wouldn't change a thing