Jacket: Remember in the '90s how you would have rather died than wear your collar turned up? Well, get over it: An upturned collar is the new scarf. Equally good at keeping the chill off your neck, savvy travelers will tell you that the look never went out of style in ultra-cold cities like Chicago.
Top: Carlyn epitomizes the simple, pulled-together look of women living in Virginia-Highland, but the secret is that most of it is part of Met Deluxe's dress code, which demands neutral colors. Though this black-collared shirt may look Ralph Lauren, a working girl has to watch her pennies. She opted for the Target version at only $16.99.
Skirt: When it comes to linen, however, Carlyn doesn't mess around. At an affordable $34, this easy, breezy skirt was purchased at Banana Republic.
Shoes: Dirty Looks has a pair of these Me Too flats in blue. Also like Dirty Looks, Carlyn is from Florida, so most of her shoes are flip-flops that let the slightest breeze keep feet cool. When Met Deluxe told her she had to wear close-toed shoes to work, Ms. M made this pair the only toe-hiders she owns.