So what do you all think about doing this?

My Mom gave me a few bucks for my birthday. So I went second hand shopping and for $25 I picked up 2 pair kaki (sp?) pants, 1 pr cords, 1 pr jeans, 1 pr shorts, and 1 skirt. Here's the catch: They all fit me (kinda), they just don't look super great, the way that if I bought new for $25 a pair or more, I'd make sure they fit kinda way. If I can loose 5 lbs, then they will all look fantastic sort of don't fit.
So, now I'm feeling pretty motivated to dump a few lbs. I'm one of those skinflints in the cash dept. So I think that the fact that I could be wasting $25 is more of a motivator than loosing the 5 lbs to look good in the clothes...

Does anyone else do that? Or am I crazy (read stupid?)

I hear ya, Chubbamama! I have gone without anything new and pretty all winter and most of the summer because I refused to buy a bigger size. Now that I am right where I want to be (give or take a few off-program days! ), I definitely need some new fall wear. I used to but clothes based on how great the deal, not how well they fit. So now I hate my wardrobe. I am going to weed out all of the stuff that I hate or doesn't fit, and only buy classic, elegant pieces that fit beautifully.

Starting with my dream black cashmere ruffly sweater for $298. Just kidding!

I think its a good idea. It will be very motivating when they start to look better on and it gives you a good incentive to stay on plan. Five pounds is a fairly achievable goal for the next couple of months and it is good to have a short term goal. I have so many clothes that are too big for me that I tend to buy something about half a size too small (but still fits okay) then slim into it. It doesn't take too long, probably because of the exercise because my weight loss is very slow atm. Then I can get a lot more wear out of it until I hopefully get too small for that size. A lot of smaller sizes I have bought this year are getting too big on me and I have had to replace them already which can get expensive but it is a really great feeling when your clothes that you slimmed into are now too baggy!

Before I started my current weight loss plan, I bought a pair of jeans that were on sale that were size 24 (I was wearing a size 28 at the time). I couldn't even get the pair of pants up my butt, but now they fit fine.

It can be very motivational! Don't lull into thinking that it's "not a loss of money" and not be motivated. Think of how good you'll look in them.

At the same time though, don't go crazy. Don't run out and get "goal jeans" that are a size 6 or something. I did that once when I first started trying to lose weight and let me tell you...one look at those pants and all I thought was "Like I'll ever get there! Pass the chcoclate frosting, please." But I think a good "snug" fit might be some good motivation! I just don't want to set myself up for depression when the "goal jeans" I bought don't go over my knees.

I think it's a fine idea. My mom bought me a pair of jeans for Christmas that were size 13....I couldn't get them even halfway up my thighs. I cried and cried about it, and since SBD, they're my favorite pair....but they fall down. I can pull them straight off without unbuttoning them or anything. So now I need a new favorite pair of jeans!

Thanks guys! I'm hoping that my goal can be achieved, after all, it's just 5 lbs for this stuff to look great! I'm getting a drawer full of different sized pants, and it's nice to have some that are too big, and give them to my neighbor who needs a shove out of the 80's! Lol!

Just don't wear them while they're too tight. Nothing worse than visible panty line!

I'm hoping that with these clothes washed and folded and put away under all the clothes that do fit me, I won't even be tempted! Lol. I'm not a big fan of the panty line, or the visible panty thing that some seem to go with!