I've experienced a few awkward moments with friends where they have asked me things like, "Do I look fat in this?" or "Should I wear this or this on my date?" In most cases they look absolutely fine and I can simply put on a happy face and tell them they look amazing. But there are those instances where the feeling of overwhelming laughter is rumbling in my belly at the horrible and unflatterining ensemble they chose.
I feel with friends your supposed to have that open and honest relationship where you can tell them what's on your mind, but sometimes it's difficult- especially when the truth may hurt their feelings.
One method that I have used when my girlfriends enter the room looking less than chic is to remind them of all the other adorable or sexy outfits they have worn on other special occasions. Usually this remark will lead us to the closet where I can give them my opinion on what piece would be better suited for them. This has eliminated any uncomfortable conversations.
A little reassuring and a few compliments go a long way. Sometimes it's not even the clothes that aren't appealing. Sometimes it's just a matter of self-confidence. For those blind date jitters that she may be experiencing pre-date, tell her that anyone would be lucky to have her and send her on her way!
This article has also helped me deal with situations similar to what I mentioned above. Check it out!
http://www.ehow.com/info_12161967_someone-feel-confident-clothes.html
