I think it's cute and can be worn as long as where you're going is very casual. Football games, bonfires, just-because get togethers with friends or family, etc.
Also, try easing into the look by wearing socks/cuffs that are the same color as the leggings and/or the boots before journeying onto more conspicuous colors.
-- Edited by pollyjean23 on Tuesday 9th of October 2012 12:22:14 PM
I'm seeing boots with knit socks (or cuffs as in the pictures below) more and more in blogs and Pinerest. I'm not sure if I like this look in theory or IRL as well. I think it looks cute in photos and maybe even on girls in their 20's, but am I too old to pull it off? I'm 40, so not quite out to pasture yet, but is it too cutsy?
I'm coming down on the side of not a fan other than the cold outdoor occasions mentioned. But, "slouchy," "scrunchy," etc. are not in my vocabulary. My personal preference is cleaner, more tailored lines.
This made me think of a photo of Kate Middleton where I thought the look was super-cute - she wore with a skirt. I like that the socks aren't too thick.
Well it looks like I might be in the market for some new socks.
I really think I like the grey sweater sock look with brown boots. I saw a suggestion on Pinerest to use sleeves from an old sweater, so maybe I might be in the market for an old grey fisherman knit sweater too.