I kept my old clothes in a box just in case. And now I’m glad I did.
I was very careful with bigger sizes in my purchases. Used a lot of Kohls freebie bucks. Lots of neutral colors and styles that were versatile.
Shirts aren’t as much of a hassle, but pants were a big deal. Obviously belts can help on the way down, but one thing I found enormously helpful both in the way up and down were those infomercial buttons that are basically pins that let you change where on your waist the pants button goes.
The issue I haven’t figured out how to mitigate is that my chubby bits are evaporating unevenly, and the way my shirts rest currently makes me look like I have preteen girly nipple nubs.
I’ve been going with the route of wearing them until they fall off of me. I’ve gone thus far from a size 28+ to a size 12/14, and I’ve only just started getting rid of my 26s. Us girls have a slight advantage in that most of us have hips, which can hold up too-big pants for longer. Also, belts.
Also, I’ve been buying a few things at each size. Usually, I have a 2-4 size spread where the clothes are acceptable (right now, 12s - 18s, though some of the latter are getting ridiculous). I wouldn’t advise spending a lot of money if you intend to lose more, though. It’s so freaking frustrating when you have to stop wearing a pair of jeans, and it feels like you’ve just gotten them. Or a nice jacket. Grumble.
This stuff kicks ass (pro-tip: it’s also fantastic as a makeup primer!). I’ve lost about 60lbs. since December, and I’ve been buying disposable stretchy clothes at Kohl’s and Target, with a few cute frocks tossed in here and there, since I intend on losing another 40 or so…
I lost a bunch of fat and am in the process of gaining a bunch of muscle, so I’ve been in your boat and still am to a certain extent.
My solution is to just buy cheap clothes in the first place. Everything I own basically is from the Gap, Banana Republic, or J Crew, and I typically buy them only when they go on sale (which is almost all the time) or I get an email coupon or can find a good promo code.
Also, tailors can do great things. I got a bunch of work shirts taken in around the middle. It’s like getting a brand new custom-made shirt for like 10 bucks.
Regarding the chub rub, there are a number of options, including roll-on sticks (that supposedly leave a film on your thighs to reduce friction), powders (I find Curash quite good - they do an adult version but it’s exactly the same and I find the baby verion tends to be cheaper), bike shorts, knickers with legs (my favourites areSloggi long leg briefs). Check out the chub rub cures tag on Fatshionista (warning: fat positive site) for some other options.
If you find a solution that works for you, dresses and skirts will open up a lot more clothing options, because they are less ‘fitted’ than trousers so they last longer.
Don’t fret too much about the clothes you threw out, I’m finding that as I lose weight, my body shape is a lot different to the shape it was as I gained the weight. So the clothes that fitted you well before may not fit you well now.
One thing I have done is buy a basic sewing machine, and taught myself how to sew my own A-line skirts! This allows me to make them to fit (I currently have a HUGE hip to waist ratio with more than two standard sizes difference between them). I then buy cheapish tops to wear with them.
This bears repeating. I saved a number of my favorite things that were still in good shape when I was getting rid my old “skinny” clothes. As I’ve been losing, I’ve been excited to pull out these clothes and try them on. Some of them fit well. But others fit so weirdly. Like pants that are now huge in the waist, but still snug in the tummy.