What to Wear to Your High School Reunion

Six ensembles that celebrate your success.

By Eileen Conlan

Oct 29, 2007

Dan Lecca

A+ Fashion

INDEPENDENT STREAK
You were always such a goody-two-shoes, but you've since chucked your hall-monitor ways for a rules-bending bohemian life. Accessorize your dress with colored tights and bright heels. The more you clash, the better you look.

BUDDING CEO STATUS
Remember those thick Buddy Holly frames everyone made fun of? They're in. Slip them on with a long pencil skirt and lots of layers up top, and show everyone that this is one bookworm who has morphed into a style icon.

NEW BODY
Check your former chubby band-geek persona at the door and wow everyone with a skintight dress and booties. Stick to dark, body-defining colors and give those bitter woodwind-section rivals a reason to stare. Take that, oboe bitches!

HUSBAND, 2.5 KIDS, AND WHITE PICKET FENCE
Once voted "Most Likely to Die Alone," now you've got it all. Coordinate your outfit with an element of your hubby's without going full-on Jada and Will. A shell, pencil skirt, and cape pull together the whole smug package.

HEFTY DIVORCE SETTLEMENT
Your scandalous split was hashed out in every newspaper. Keep them buzzing by showing up in your favorite fur coat thrown over a red-carpet-worthy dress — after all, your ex is paying for it.

BUN IN THE OVEN
At the 10-year reunion, the entire girls' lacrosse team chided your workaholism — you'd simply forgotten to have children, they sneered. Make like Angelina in a long jersey jumper that clings in all the right places, revealing your on-trend baby bump.