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I bought a bigger pair of jeans early on - like 8 weeks or so? I work those until 20 weeks with the belly band! I also had a few pairs of work pants that were slightly larger from when I was heavier that I wore. I didn't wear maternity pants until 20 weeks and shirts a few weeks later.

So far I've been using an elastic band on the button of my pants. I'll probably get a belly band for the second trimester... Not sure I'll be getting any real mat clothing unless it's maybe for work.

I gained a ton of weight in the first trimester, hoping to slow down now! But yeah, I was in maternity pants at around 10 weeks? Wearing flowy dresses and ditched regular pants at 8 weeks though...

I was really excited and bought & ordered some maternity clothes early on. And a lot of it didn't get worn (or still haven't been worn) until probably month 6. I did the elastic loop around the button on most of my skinny jeans until month 6. I have 2 Bella Bands that have been worn a couple of times from month 5-6, probably could still wear them now (30+ weeks) if I wanted to.
I would suggest getting a few basic bottoms in maternity as those are what I've gotten the most wear out of. I bought 2 pairs of skinny jeans (1 full panel and 1 under-the-belly) that get worn the most. I wear a lot of leggings too (I like the "skinny style" w/long tops & sweaters too).
I found A LOT of my regular sweaters and tops can still go the distance. And I've bought some larger regular tops for length. I just wear long cami/tanks underneath if I'm worried at all. I love the GAP Long & Lean and Secret Camis too.

I used the belly band (Target brand) around 9 weeks. Then I think I started maternity pants around 12 weeks but still could wear regular pants with the band till 17 weeks or so. When I just gave up to the comfort of maternity full time.

I needed maternity work pants first (probably by 14 weeks) because all my professional clothes are pretty structured. For casual wear I'm only recently getting into maternity (almost 19 weeks). I continued with my leggings and had a larger pair of jeans from when I was heavier.

I did have a bella band that was nice for when I was at the bloated stage, but I wasn't crazy about it for a full day of work once I was out of the first trimester.

I went straight to buying maternity because larger sizes don't fit me well anywhere but the belly.

@JerricaBenton: Gem! I didn't even remember this cartoon until I saw your avatar.

@MsLipGloss: Love her!

After 20 weeks

By 8 weeks my regular pants were feeling tight, so that was the point where I started leaving my regular jeans unbuttoned or wearing the pants that used to be too big (fat pants, if you will). I'm thought about buying a size up but since it's only my belly bloating, they won't fit everywhere else-- pre-preg my stomach was always the issue anyway.
At 10 weeks now, i just bought my first pair of maternity jeans and it will be them, unbuttoned regular, and fat pants for a few more weeks, but the mat pants are SO much more comfortable!
Shirts I predict I'll be able to wait a while. I tend to wear loose or high waisted tops anyway.