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My wife has the 38 while I have the 42. Looking at the cases makes them appear so much different, I was surprised to learn the actual screen size dimensions are very minute.

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https://www.imore.com/which-apple-watch-size-should-you-get
 
I have never regretted the 38mm. I tried both sizes in store, with a variety of bands, and the 38mm just felt much better on my wrist. Both looked fine, but I slightly preferred the look of the 38mm on my wrist as well. I've had my 38mm Series 0 Sport for 2.5 years, and soon I will upgrade to the 38mm S3.
 
I got the 42 mm just because the price difference wasn't enough to sway me into getting the smaller one. The text size doesn't bother me. I can see everything just fine. I do have pretty bit fingers for a woman and that ultimately is what led me to get the 42mm. Also, I do have bigger wrists so the 42mm does sit nicely on my wrist. *shrug* that's my 2 cents.
 
FWIW I ended up keeping the 42 and am very happy with it. I’m pretty sure I’d be happy with the 38 too.

I got a really nice knockoff black mesh band and wear it about half the time, swapping with the stock black.
 
FWIW I ended up keeping the 42 and am very happy with it. I’m pretty sure I’d be happy with the 38 too.

I got a really nice knockoff black mesh band and wear it about half the time, swapping with the stock black.
Good, at any rate both watches are fine. It's just a feeling of whether you like the feel of the 38 or not.
 
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