Connecticut, although close to NYC, is much more conservative, and it tends to have a kind of "old money" feel to it. I would choose classic shapes and colors, tasteful embellishment, and clean accessories. Here are some recommendations:
1. Vera Wang Lavender Jewelled Neck Dress, on sale for $357 (down from $595) at net-a-porter.com: Classy and formal, this dress will serve you well for years to come. I adore the jewelled neckline and the metallic color is hot.
2. Banana Republic Silk Asymmetrical Dress, $175 at bananarepublic.com and stores nationwide: This dress hits on two trends: Grecian and bold color. Choose chandelier earrings and you're set to go.
3. Tracy Reese Scalloped Dress, $310 at eluxury.com: If you prefer classic shapes and black, you can't go wrong with Tracy Reese's sweet interpretation of the LBD.
4. Rebecca Taylor Beaded Chiffon Dress, on sale for $266 (down from $355): I rarely feature too many black dresses, but this one is so sweet, so pretty, and so wearable.
For accessories, choose a simple box clutch, low kitten-heels or peep-toe pumps, and classic jewelry (pearls, diamonds, chandeliers, bangles). Avoid anything too fussy, experimental, or elaborate. Think sophisticated, subtle, and simple. Have fun!