Hi Legs; I've missed seeing your outfits around here, and hope you're now in a place where the future looks as bright as your palette often is!
I think you look great in these, and am not much use aside to say there was a BBC series called something like "The Science of Attraction" and key takeaways re first impression dressing for women were rather sadly typical: V neck, pendant to focus the eye, defined waist (at least softly defined if not bodycon). [If you can track the episodes down online you might enjoy them!] So these outfits are very close, but you may want to semi-tuck or knot at one side or something.
On another note, I'm also a skirt/dress person and from what I can recall of my online dating days didn't change that up. In fact TBH with your legs, a skirt a few inches above the knee and some casual heeled sandals will no doubt be upvoted even by dates dressed in rags!
I firmly believe job hunting and dating are exactly alike and at some point you have to ask yourself how much you want to twist/conceal the things that are important to you. Sure, you land the job/person of your preferred sex but then there's pressure to keep your real self tamped down or more accommodating and for most of us that gets old pretty fast.
So: do you want to attract the greatest number of guys in Seattle* or the *right* guys -- ones who think your typical style of dressing is positive at best, neutral at worst? [I'm job hunting so trust, this isn't an entirely rhetorical question!] After all, Typical T-shirt Guy probably wants someone who isn't looking to change him up -- though he may evolve on his own.
I have to laugh a bit because I'm part of an oft-mismatched (in terms of formality and other things) couple and I'm sure we're judged. I just figure in terms of clothing he makes me look cooler and I make him look classier....
Best of luck to you as you navigate the dating waters. Remember to constantly ask yourself whether you like him instead of worrying whether he likes you.
*another PNWer here so I feel your pain
