UGH! LAME! That sucks and I'm sorry you have to do that. It's even worse that it's for work, eh?
Do you have any strategies for eating that will help you? You could always treat it as a challenge. Make a chart, get some stickers, ka-pow! MOTIVATION!
Try not to get too down on the clothing purchases. In my experience, even though you don't like them right now, you never know when they might come in handy! I have a few pieces myself that I "had to buy" for teaching practicum that after a few years, cycled into my regular clothing rotation.