What to Wear: Italy in May

Maddison wrote in with a request for a “grand-tour” vacation coming up in May:

I am a plus size 20 year old girl and I am going to Italy from May 2-14 and I need some clothes ideas. I don’t know what to wear and its harder being overweight (size 22). Please help!

The easiest way to look cute while traveling is to stick to a basic color palate. Red, black and brown will be to mix-and-match and keep clean!

Dress – With a flattering crossed neckline, this fun dress is only $48.
Shoes – T-strap pumps are darling! And Me Too is a very comfortable brand to wear traveling.
Sweater – A versatile black sweater with a bit of sweet smocking. Works with both the dress and the jeans.
Tee – Basic black layering piece from Old Navy.
Jeans – A dark trouser cut pair from Old Navy.
Sneakers – A pair of comfy, Euro-style sneakers.
Scarf – In pretty black and white silk from Forever21.
Sunglasses – Aviators also from Forever21.
Bag – Appears way too cute to be available for $18 from Forever21.