You are going to need a totally different shopping strategy for the losing process than how you shop when at a stable weight. Basically, when you’re on the way down, clothes are disposable, temporary friends. They’re only going to be with you for a short while, so don’t invest and don’t get attached. You can view the local Goodwill as a lending library if that helps.
The first thing you need to learn is that you no longer have to buy something just because it fits. This becomes more and more true the smaller you get (up to a point, of course—if you go down to a size zero you’re going to have trouble finding things that fit you again.)
Seriously. Sit with this for a moment. You no longer have to buy something just because it fits.
There are going to be boots that zip over your calves. Lots of them. Most of them even. You no longer have to immediately buy that pair that zips, because there will be more. Cuter ones at lower prices. Things will go on sale.
Things will go on sale. In your size. There will be cute clothes left in your size. On clearance racks. I’m not kidding—it’s true!
I have three pairs of thigh-high boots in my closet right now. I bought them because they fit over my thighs. It took until after the third pair before it occurred to me that this was no longer a reason to alert the media. It’s not that I regret having them, but I can see how silly it is to own three pairs of thigh-high black boots just because they fit.
I also have about a million pairs of tights. It was winter when I realized that I could now wear S/M tights, as opposed to M/L. S/M is the smallest size of tights. I was nowhere near goal, but I could fit into the same size I’d be wearing at goal. It was the only area of my shopping where I could unfetter myself, and so I bought a lot of tights. A lot. They have an entire drawer in my dresser plus a hanging shoe organizer.
Anyway, in general, when losing, don’t spend a lot of money on anything. Don’t buy a lot of anything, even shoes. Your feet shrink. It is common for people to lose a half or whole shoe size when they lose a lot of weight.
Also, your sense of style is going to change radically during this process. Your body shape will change, as will your perception of yourself. The things you buy when 40 pounds from goal are not going to be the things you want to wear at goal. You can’t just scale things down, either. If you try on something in a size eighteen and think it’s cute on you, that does not mean you should also buy it in a size eight so you have one at goal. It might not be cute on you in an eight, or it might be way less cute than your other size eight options when you get there. Avoid the temptation to “buy ahead.”
Stay focused on things that fit you now, that are cheap, and are just enough to get you through. Some people go down a size every few weeks, so the clothing situation is really quite temporary.
Before buying anything, make the most of what you have. Wear existing clothes as long as you can. Get a belt with a lot of holes, and use it to stretch the lifespan of your pants. Don’t get absurd about it, but do try to make them last. Once you go to a smaller size, those larger clothes are gone forever. Make them work on their way out.
Keep trying on everything in your closet. Try on all the pants, and stack them in descending order of size. The ones that fit you now go on top, the ones that almost fit underneath, the ones that are a reach under that. Every week or two, try on the top pair that almost fits. Do the same thing with shirts, dresses, etc. Believe me, it sucks to realize you skipped over a totally cute item of clothing and missed its window of attractiveness. Better to be organized about it. If you already own clothes, make sure you wear them when they fit!
What do you buy? The smallest thing you can squeeze into without provoking bystanders to call the Camel Toe Police. A little muffin-top is okay, as long as you wear a baggy shirt over it. You have lots of baggy shirts in your closet already, so this is no problem. You don’t want to get anything that is nicely tailored to your body now, because it will be baggy in a couple weeks. Go a little tight instead.
Stretchy clothes are your friend for this. Elastic waist bands. Skirts and dresses instead of jeans. Just do us all a favor and don’t do the giant shirt with leggings routine. It’s not attractive or fashionable. I know it’s convenient, but stop it. Really. You can be just as comfy in a pretty skirt out of a stretchy fabric with some nice sandals, as you can be in leggings. You’ll feel better about yourself, too, I promise.
You are going to need to replace all your underwear multiple times. This is disorienting as crap. I handled it by going to Costco and buying one six-pack in each size. I stacked them in descending order of size, and when bigger ones got too big I threw them away. No huge investments in lingerie (or anything) until at goal.
I did the same thing with jeans. Different brands of jeans are sized differently, as you know. It’s not like I could buy a size ten in one brand when I was shrinking out of twelves in another, at least not without trying them on. I wanted to avoid the eternal shopping struggle of trying to find cheap new/used jeans in whatever size I was at the moment. I still wanted to have pants that fit. I picked a brand—the Gloria Vanderbilt jeans they sell at Costco. I bought three pairs in a size when I was bigger and still avoiding skirts, and then two pairs in a size when smaller as I was showing off my new tights more. Because I only bought the one brand, I knew for sure that a fourteen was larger than a twelve without any dressing room time. Once I got to goal I went back to the normal thing where you try pants on before buying them.
Get bras a little more often than you think you need to. I know that bra you’re wearing is still sort of holding your girls on your body. Sort of. But a well-fitting bra can revolutionize your entire silhouette. It can make all your clothes more attractive, make you feel years younger, improve your posture, and get you free drinks. Seriously. Go buy a new bra. You’ll thank me.
Overall, just remember that clothes while losing are a stop-gap measure. Your style will change, your body will change, and you will shrink out of everything you are buying while losing. Get just a few things to tide you over to the next size down.
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