Absolutely! Even at the weight I'm at now I am happy in a t-shirt out walking.I know I still look over-weight but compared to what I was I couldn't be happier.
The problem is I spent my working life in mechanic's overalls.I didn't own a proper suit until the late 90's.I've always dressed casual,or comfortable as I like to put it.
Luckily my sister-in-law is a great clothes shopper and I'm house-sitting for them at the end of the month.When they return from holiday I will ask her to take me shopping.She doesn't know I've lost weight,that will surprise her I think.