I'm keeping the pieces of an outfit simple here and letting the plaid do all the talking. A blazer is an instant outfit dress-me-up while the red loafers tie into hues of the plaid shirt and make me look like I've given thought to the pieces working together. I'm perfectly casual and comfortable but don't look like I just rolled out of bed ... which I might have.
Jacket: Zara (worn before - sim on sale, bolder print)
Shirt: Lands' End flannel (worn before - sim & sim both under $20, pricey)
Jeans: Banana Republic factory (sim, sim under $20)
Rings: c/o INPINK (sim under $10), F21 (sim under $10, sim)
Shoes: J.Crew cleo (sim factory version, penny loafer style, studded heel on sale)
Bag: Coach turnlock tie (small version on sale or here as well, sim on sale or pricey)