ChristelJ - I am a big fan of matching, right down to my sunglasses too.
Jenni NZ - Indeed, I think an outdoor restaurant or bar would work well for the first outfit. Of course swapping the heels with sneakers is something I would do more often, but it was fun to experiment with shoes for a different look from my usual sneakers and sandals.
Jaime - You are spot on with both outfit assessments!
Sisi - Thank you for looking!
Angie - *happily collects killer rating* I don't wear blazers daily anymore since I WFH, but it's still nice to pull one out every now and then to mix things up. I've always enjoyed a nice blazer for a little extra polish to an outfit.
Firecracker (Sharan) - I agree that black sneakers would also work for outfit #1, but I wanted to push my style muscles and try something that wasn't my usual sneakers and sandals. I've found shorts can work well with heels if the shorts are on the dressier side. I have also learned that I enjoy jackets and blazers with shorts, but the length matters to my eye. The longer the shorts, the longer the jacket or blazer. Your denim shorts and linen blazer look like a perfect pairing!