What to Wear: Red Shirtdress for All Seasons

Depending on where you live, you’re either dealing with incredible heat or overcast cold this week. Luckily, there are a lot of clothes that can handle both summer and winter weather (no matter what time of year it really is). Cynthia wrote in with this request:

I just bought a cute shirtdress and was wondering whether you could come up with some outfit ideas around it. It’s red, hits slightly above the knee, has short sleeves, and came with a wide black belt. I’d like to be able to wear it in spring, summer, and fall if possible; I’m thinking layering, but not sure how best to go about it. Your help would be greatly appreciated.

I’m such a fan of shirtdresses! Here’s my recommendation:

Warm
Dress – An approximation of Cynthia’s. $100 from Nordstrom. In her case, she’ll need two belts to replace the sash: one summery in light leather and one in dark brown for fall.
Shoes – Summery espadrilles.
Straw tote – From Spiegel for $20.
Headband – From J.Crew in bright silk.

Cold
Cropped jacket – Houndstooth is fun for fall. This little jacket would also be nice with jeans and a sweater.
Boots – A good pair of boots is priceless. This pair from J.Crew will go with anything, in this case a red dress and a pair of tights.
Handbag – From Target.

Okay, that’s it. Bring it on, cold weather. I know summer is on the way here in SF, but I’m really tempted to unpack the tweeds. My ideal outfit today would be a pair of wool trousers, a thick cableknit sweater, bright wool coat and leather boots!