I just buy clothes as I need them. I figure it's the price I pay for looking better :P. I do shop sales and clearance. But once something is big enough to not be flattering I say goodbye to it!
eBay, Salvation Army and thrift stores have been my friends. I have been stalled for a awhile so I did just buy some new clothes since I might be this size for a while. But I shopped carefully and got pretty much a new wardrobe for about $300. I have not been this size in probabluy 10 years so I figured if I am going to get stuck I may as well enjoy it. Also as someone above said, you can get lots of things altered. Since you are a fairly small size you should be able to do real will at thrift stores, Salvation Army and even clearance racks at the stores. Don't spend too much, since at yor size just a few pounds lost can make things too big.
Hmm, selling on Ebay sounds like a good idea. How much do you usually get? I have a lot of super cute clothes that haven't been worn much at all that I'm looking to be relieved of.
JayLei that is EXACTLY what I think, too. Having your fat clothes around to fall back into is a terrible idea!
I will only go out to buy new clothes when I'm absolutely desperate. Like many others, I still have some clothes stashed away in smaller sizes that I'll eventually wear. With the colder weather having arrived, I'll probably hang on to some ill-fitting clothing that is ok if I layer it. And shopping is done at consignment/thrift stores first; new clothes are only an option if I can't find it used (except undies). That's just a personal thing: I value re-use over manufacture of new goods. No one but me can tell the difference anyway, and I often find some original items in the consignment/thrift stores (whereas the new stuff all looks the same to me...)
I bought a small amount of new clothes after my first 50 pounds, but I'd only gone down a little over one plus size - if I could have waited a little longer, I would have.
I absolutely needed new bras, as the old ones no longer provided any support. I was swimming in my pants, and I didn't have any fall tops that weren't more than a size too large.
So, I went ahead and bought a small number of new things, just so I'd have a few items that actually fit to get me through the fall and winter seasons. It helps me feel good about the loss, as it does show more in clothes that fit better. I didn't buy a whole new wardrobe, just enough to get me through a week at work. I mix in older items that aren't too ridiculously large, or wear the big old stuff on weekends.
I will probably have to do the same thing in the spring, when I'll be down another size and my old warm-weather clothing no longer fits.
It's a very personal choice, though, and depends upon a lot of factors that vary widely person to person. If I had kids or was a student or unemployed, I'm sure I would have found better uses for that money than spending it on clothes that will only fit for one season.
I'm almost through all of my stashed away smaller clothes. I have 4 pairs of pants that should fit in the next month or so, and that's about it (aside from a couple of skirts/dresses that won't fit for a looooooooooooong time!).
I've been making do with my big sweaters, because I usually like them big anyway. However, they're 2/3x and now I'm fitting into an XL. I'm anticipating having to replace them in December-ish. I had to buy some new pants yesterday. I found some for a really good deal yesterday, and ended up buying 3 pairs in my current size and 1 in a size lower (b/c of color options). I've also had a friend giving me her hand me downs as she loses weight, but I'm gaining on her so that won't last much longer!
As a PP said, I don't want to feel frumpy along the journey, so if it's not flattering, I don't wear it. This goes double for pants/jeans.
I also buy most of my clothes at Goodwill and other thrift shops. While my weight was dropping, I went every time my jeans started to get loose...and would just downgrade (or upgrade) to a smaller size....and also donate back the ones that had become too big.
It's great thrift shopping because:
1. It's extremely cheap to go and replace a previous wardrobe...and easily affordable to do it often while you lose. And I learned that putting on a smaller size made people suddenly notice the loss and motivated me even more, as I went along.
2. You already know how they'll launder.
3. I often don't like the current style of certain things...and when a style is in fashion, that's pretty much all they sell in the stores. But at thrift shops you can get a whole variety of past styles that you might prefer (and look better on you) over the current styles.
4. You may fit in different sizes depending on the brand. At thrift shops, you have a huge array to try on and choose from and may end up with several different brands in different sizes. For instance, I worked my way down in Levi jeans to 29 waist, but last time I went, I decided what the heck, and tried on some "skinny jeans" from Apple Bottoms brand...and they looked great so I got them. In regular stores, it would be unlikely that I'd go and shop in the teens section...but in Goodwill, they're all in one place, on one set of racks. There are literally hundreds of jeans in almost hundreds of sizes to try on....the dressing rooms are not locked...you just go in and use them and don't have to get a number or anything like that. You are free to just try on armloads of brands and sizes at whim.
I would never pay the exorbitant prices (compared to thrift shops) they charge in the regular stores. And once you wear something new, it's worn. It's only new once...so why pay those prices just to enjoy it NEW one time? And heck, you can change your wardrobe every time you lose 5 lbs...because it's so inexpensive.
Also....people who can afford expensive clothing tend to donate more because the expensive clothing holds up longer and they don't tend to share or pass-down clothing as we regular folks need to do. I have myself a whole wardrobe of really nice, expensive...short/petite jackets (to wear with pants or a skirt) that would cost a small fortune in regular stores...but I got them for 5 bucks each. And if you really want to get some expensive clothing for cheap prices, go to the thrift shops run by the ladies auxiliaries for different hospitals...like the Palm Tree thrift shop at Paoli Hospital in PA. Most hospitals have them....they provide additional funding (which is the main purpose of these auxiliaries). And holy cow, if you go to some of these in fancy areas, you can literally get designer brands, for dirt cheap...many with the tags still on them and never worn.
My father got multiple Armani suits, never worn and with the tags still on them years ago at the Palm Tree at Paoli Hospital. Most of the auxiliary women there are doctor's wives donating their time...and often buy expensive suits that their husbands turn out not wearing for one reason or another so they just donate them to the thrift shop, brand new...tags still on them.
Anyone who has never tried thrift shopping should try it. You don't know what you're missing....seriously.
Look, I have worked very hard at overcoming a tendency to binge when eating, so I am also trying not to transfer that to shopping. No spending binges. No complete wardrobe replacements in one or two weekends of power shopping.
Gradual wardrobe attrition & slow replacement, item by item, as absolutely needed: That was my strategy during the weight loss. Only now when I've maintained for over a year, have I felt comfortable buying more. And the recession & general cautiousness about the economy -- not to mention handling mortgage payments for the first time in my life -- have kept me frequenting eBay and sale racks at TJ Maxx, Marshalls & outlet stores.
I was fortunate in that the most dramatic stage of my weight loss occurred during the long Northeastern winter and late fall. Roomy sweaters were my friend. I remember thinking that my behavior was sort of like a teen hiding an unwanted pregnancy, only the opposite, as I was hiding a **shrinking** stomach. Same goal: I didn't want people commenting on my changing body & didn't really like going public with what was happening to me.
This also meant that I didn't get a lot of compliments and "wow!" over my weight loss until after Christmas. That was when I decided that I needed new pants, and the after-Christmas sales coincided with that. That seemed to be the big reveal, at last. I got comments before then, but they were more tentative.
That's why when people here are unhappy because no one's saying anything to them, even though they've lost quite a lot of weight, one of us on the board always pipes up & asks what kind of clothes they've been wearing. Personally, I can attest, it makes a big difference once you step out in public in clothes that actually fit.
I'm another for gradual replacement using thrift stores (I heart Value Village!!) first and sales next. Up to now it hasn't really been an issue because I have had clothes to shrink into and any clothes I purchased were for the goal. I am almost out of clothes to shrink into, though, with a bunch more pounds to go - hopefully current clothes will work until I reach goal weight when I can sort things out for keeps. If not, see above.
I own three pairs of pants that fit at all times. Shirts are often too big. I live with that. Although a trip to an amusement park last weekend reminded me that I really do need new shirts. It was the tallest roller coaster in the park and with each down hill I felt my shirt ride all the way up, possibly above my bra! Fortunately the picture is taken at the top of a hill where gravity kindly lowered it. But even in the picture, that shirt was flapping in the wind and added 20 pounds.
I like that Fall/Winter is here now for the reasons Saef mentioned. I'm wearing a too-big sweater, but it's just plain comfortable. It doesn't matter that it could be smaller.
I too like thrift stores, but I've been struggling with fit in pants because I need to try them on and there are NOT dressing rooms...nor would I use them. LOL! I search wearing gloves, I am NOT trying them on until washed.
I wait until they look too frumpy, but I try to keep wearing the same stuff for as long as possible so I dont have to keeping buy new stuff all the time.
I noticed the other day that I keep on hand close to my hip to hike up my pants all the time -- so I went and bought new jeans!! haha
I keep wearing the same stuff until it's falling off, and then I buy only what I absolutely need to for as cheap as I can get it. So far I've only lost two jeans sizes in like 43 lbs of weight loss, but I skipped from a 16 to a 12.
My shirts haven't changed much (I wear some older, bigger ones but also had some smaller ones that fit again), mostly because I carry a lot of weight in my torso and my cup size hasn't shrunk at all. Fills out those shirts.
I'm trying to scrape by until I hit the weight I want, then I'll replace things one or two things at a time. I'm not a big spender, and I've never had a problem blowing too much cash on clothes or anything. I LOVE clothes, but that's one area I've always had a lot of self-control (weirdly enough).
Do what you can afford and what you feel comfortable with, I guess.
Shirts are often too big. I live with that. Although a trip to an amusement park last weekend reminded me that I really do need new shirts. 
It was the tallest roller coaster in the park and with each down hill I felt my shirt ride all the way up, possibly above my bra! 
Fortunately the picture is taken at the top of a hill where gravity kindly lowered it. But even in the picture, that shirt was flapping in the wind and added 20 pounds.
