What a great summary did you write Suz! I use to wear a denim jacket over a summer (or smarter) dress/skirt outfit from what if feels like ever! And, wow, I already knew some of your items here but would have loved to see you modelling that gorgeous outfit!
We have had threads about juxtaposition in the past I think and this is a theme also fascinating me so I always save other's ideeas for future use, now will cite from my past notes, think it mostly were Angie's directions but may have added other's contributions, too(?). To be honest I unfortunately do not remember where and when exactly did I save these:
"Relaxed Glamour and Elevated Everyday.
It’s very current to relax a glam look, and to elevate an everyday casual look. This brings us back to the important theme of juxtaposition.
You might relax dressy pieces by combining them with denim, motos, aviators, slouchy bags, crossbody bags, or casual footwear.
Wear a tee under a blazer.
A cropped sweatshirt with a fancy skirt and heels.
Throw a tuxedo jacket over utillity pants or leggings.
Wear dressy clothes with flats.
Add sparkle to jeans.
Wear a cashmere wrap or ruana with joggers.
Add a silk scarf and pretty sandals to parachute pants and a shirt.
Add chunky glam necklaces to slouchy sweaters, sweatshirts, and knitted tops.
Wear a short puffer with a fancy skirt.
Add a crossbody bag to dressier attire.
Add a fancy clutch to jeans.
Style your hair, wear statement eyewear, throw on a belt, and add jewellery to a simple shorts and tee outfit.
There are countless ways to relax some looks and elevate others. Choose the ways that best work for you and your style."
For your further refference I have highlighted in bold those I already do myself and, I think when you attempt on doing these you really have to pay attention on each item's own condition because it can spoil the overall impression if something is overly worn out or grungy (it is surely not the case on this forum but YKWIM) just my 2 cents.