Nothing here yet.
The moment it clicked for me was a garden gathering last July, a wrap style sundress with elbow length sleeves that actually sat on my hip rather than clinging to it, and I spent the whole afternoon not once pulling at the waist or checking the neckline in a window reflection. That's the whole point of a proper curvy summer outfit, it does the adjusting before you put it on, not after.
Worn through a few summers now, the pieces that have held up are the ones in a heavier cotton or a linen blend with a bit of give in it, washed cold and hung rather than tumbled, because the thin jersey ones go see through at the seat within a month of sitting on garden chairs and office ones. If you've got nothing in this area yet, start with one dress that covers the basics, a wrap or empire waist in a dark small print, because it goes under a denim jacket for a cooler evening and takes sandals or trainers without looking like you've dressed for either extreme. The cheap ones and the good ones often look identical on a hanger, which is the trap. A well made piece has proper facing at the neckline so it doesn't gape when you reach for something, a hem that's been turned twice rather than overlocked and left to curl, and ties or buttons that are sewn through rather than just glued or stitched on the surface. The disappointing ones show it in the first wear, a zip that catches, a seam under the arm that pulls when you lift a drink, fabric that goes translucent the second you stand in front of a window. I've put back more fitted shift dresses than I've kept for exactly this reason, the fabric was fine lying flat on a hanger and said absolutely nothing useful about how it would behave once a body was inside it.
For the easy combinations, a wide leg linen trouser with a simple vest and sliders does most of the work on a hot commute, and a cotton midi skirt with a plain t shirt tucked in half heartedly covers everything from a lunch to a late afternoon that turns into evening without a change of clothes. Before I buy any of it now I ask myself one thing standing in front of the mirror: if I sat down right now, in a chair, with a drink in my hand, would this still look like it did when I walked in?
Nothing here yet.