Marianne, I'm so glad you posted this! I was wondering this myself when I put on my SL boots with my slightly A line denim skirt this morning. Both looks are terrific on you. I can't decide which one I like better although I think I slightly prefer the boots over the flats with leggings. I'm not sure I'm getting the same effect since you are much taller and slimmer. Curious to hear what others think too.

I love it with the slouchy boots, I think it works amazing!

To my eye, something is a bit of with of with the leggings look. Maybe try some shorter leggings, e.g. calf-length?

I love it with the leggings! I was thinking with the boots, it would nice to have tights. But this is all new to me!!

KILLER. Both outfits. Wooohoooo!

What has happened, Marianne? You are trendy and loving it! I’m loving it too :0). What was in that tea we drank at the Crumpet Shop?

Wow! Marianne, may I copy your first outfit? My denim skirt is a little darker, but I hope I can look even half as sharp as you do in this outfit. I also love the boots. Thank you for posting these photos.

Angie, it must be YLF kool-aid... or you slipped something in my tea :)
Thanks everyone, I am glad it works. I can't buy much right now so I'm trying to work with what I have. I've been seeing people wear all kinds of things with ankle length leggings and this kind of boots (not together), and sometimes proportions seem off, but I can't put my finger on why.
Tanya, I tried this skirt with shorter leggings before, and didn't get thumbs up.
Joy, please copy away, I'll be very honored!

I think the skirt looks great with the boots -- you've the proper amount of skin showing above your knees. Love it!

The leggings look is cute too, but I prefer the boot look -- probably because there's no line that cuts you off at the feet.

Marianne, the drug is called new found confidence and having fun with fashion and you prescribed it to yourself quite effortlessly :0). You are looking HOT.

Love, it Marianne! Those outfits are great... and I'm inspired, since I have and love that skirt. :-) Woo hoo!

I somewhat prefer the boots look over the leggings. I'm interested to see how this would look with calf-length leggings, since that is what I own.

Marianne, you do look hot! I also prefer the look with boots as opposed to leggings. I feel like the leggings make the bottom half so casual while the top half looks so dressy???? Maybe that's the point, huh? I guess I just personally don't like the look of denim skirt+leggings.