What to Wear: Connecticut Reunion

Connecticut in October…how exciting and perfect for all sorts of J.Crew. Here’s Eliza’s request:

On Columbus Day weekend, I will be attending my 5 year high school reunion. I went to a preppy all-girls school in Connecticut. I might as well mention that I am being forced to attend the reunion weekend by a friend of mine that doesn’t want to go alone. (Basically I would rather stick pins in my eyes than go)

It will be 3 days of me seeing people that I haven’t seen in a while, so I would really like to look just a little bit more fabulous than normal. The weekend will involve at least 2 day events and 2 evening events.

About me: I am 5’8″, about a size 14 (10 on top). I have a pretty preppy/classic style (a friend of mine says I dress a bit like a librarian).

I would definitely love any advice that you can give to me. While I would love to not have to spend my life savings on these outfits, I could justify certain expenses it if I can wear them again later.

For two days, you really just need two killer dresses and two great pant outfits. Here’s an example of “lux librarian” to get her started:

Evening
Dress – Dark eggplant color is flattering and will help you stand out from everyone wearing black. Plus, the structure on top is great for a curvier figure and it’s only $89.
Pumps – A platform pump with a solid heel accentuates thin ankles.
Clutch – In gray alligator.
Ring – A bold enamel cocktail ring is a great conversation piece with this outfit.
Earrings – These anthro drops tie it all together for $10. (Link isn’t working, they’re called Gelee Hoops)

Day
Jacket – In dark blue corduroy.
Top – A pretty, empire waist jersey top.
Pants – You could do this with jeans or tweed trousers, whichever is most appropriate.
Sneakers – These charcoal canvas slip ons will be perfect for campus.
Tote – From Urban Outfitters.
Glasses – From Vera Wang.

Each element here can certainly be worn again. The dress would be great with boots and a jacket for work. The jersey top could be fantastic with a skirt and those kicky pumps.