I have done this - I started SW weighing in in my shoes - was awkward as it meant I had to wear the same sort of shoes every week to avoid a false result - so even if it was hot and sunny, I had to wear my regular heavy shoes to make sure I got a fair result.
I'd been doing this for about a year or so, then hit a really annoying spell where I STS or got small gains/losses for weeks, so decided I would take off my shoes for a little boost!
Trouble is, I have to do it all the time now, and I've nowhere else to go with it. I'm also wearing light summer dresses right now which could be problematic.
Thing is - it does make a difference for me as I am at target. 1/2 a pound could be the difference between me having to pay £4.95 or not. It can work in my favour - if you are hovering near the bottom end of target its very easy to put on some heavier clothes/shoes or just leave stuff in your pockets. Sadly, I'm currently in the top end of target, so really need to be losing, but with no shoes and summer dresses I've nowhere else to go with it!