A sundress was my chosen piece of clothing for both looks.
For a casual summer outfit: I raised the hemline, wore a bag crossbody and added flip-flops. I accessorized with fun flower pins, rings, and a denim jacket for chillier weather at night.
For the transition to fall: I played off the dress' print and used darker shades of green and brown for the rest of the outfit. A longer jacket and booties finished off the look. I considered wearing tights, but it didn't seem right with the fabric and print of the dress.
necklace: [right] H&M with pearls & bow (similar)
bag: H&M snake-embossed envelope (may still be in stores; similar)
belt: [left] J.Crew piped glitter (sold here; similar);
[right] Madewell New England stripe (may still be in stores; similar; similar)
shirt: [left] Gap striped cowlneck (similar)
rings: [left] Spotted Moth via Kendi's giveaway (similar), H&M filigree (similar);
[right] Amrita Singh Deauville (sold here)
flower pins: [left] Old Navy large flower (similar)
shoes: [left] Old Navy faux-leather thong sandals (sold here);
[right] Ann Taylor covered platform bootie (similar; similar)