Typographic Message

Mango’s message tee reveals your heady romantic state with cool metallic lettering on black, all popping off the of-the-moment military inspired olive green. Layer this slim-fit tee under a black blazer and wear with a pair of dark wash denim or even fashion issue cargo pants and low-heeled booties. For a casual night out, pair it with coated black jeans, heels, statement earrings and a wrist-full of bangles.
To buy: Mango, $20
MORE: Boots for Fall Fashion
Feathers Graphic Sweater

Fashion continues to have a fascination with feathers in all forms—as embellishments, as jewelry or as in the case of the effortlessly chic sweatshirt, as graphics. The bold colored feathers pop off perfectly from the neutral background, giving this top the fashion green light to go with everything from black jeans to gray cords, to of-the-moment oxblood coated denim skinnies.
To buy: Target, $20
Foil Lips Tee

The metallic pops off the black of this super cool black tee and adds a glam effect, making this a brilliant day-to-night choice. The slightly oversize fit makes it perfect to pair with slim bottoms like skinny white jeans, black leggings or even a sleek leather mini skirt.
To buy: Topshop, $40
Printed Printed Picture

It’s easy to take a walk on the wild side when you slip into this ultra cool tee embellished with a tiger graphic. Made from cotton terry, this straight-cut shirt has the feel of your favorite worn-in sweatshirt, complete with the rolled up sleeves and wider neck. Turn this top into a wardrobe essential by wearing it with everything from jeans and corduroys to skirts and shorts.
To buy: Mango, $40
Project Social T Whiskey

Show some American spirit by donning a tee that celebrates the drink of choice for cowboys and easy riders alike. Play up the roadside bar vibe by pairing this with jeans, a leather biker jacket and boots. Or, take it out of its element by letting it top off tuxedo style cropped trousers and some feminine sparkling flats.
To buy: Topshop, $44
Zoe Karssen Oh La La

Parlez-vous chic? Then you’ll definitely want to add this tres cool tee to your fashion lexicon. Part of the collection of the Danish Design Duo, this charming top will make even the most cantankerous passerby smile. A genius alternative to a plain white tee, this shirt will add unique quality to an everyday uniform of jeans, a blazer and sneakers.
To buy: Net-a-Porter, $94
Paul & Joe Lavender Tee

An owl, a fox and a raccoon are just some of the night critters that adorn this lavender gray T-shirt from trendy French designer Paul & Joe Sister. The relaxed fit and slight asymmetrical hemline make this the perfect tee to pair with a ladylike pencil skirt and pumps when you’re feeling more rogue than refined.
To buy: Stylebop, $95
MORE: Fall Jewel Box Colors
Des Garçons Play

Comme Des Garçons Play and cartoonist Matt Groening are the unlikely dream team behind this genius and genuinely amusing tee. Bold and graphic with a pop of color and a wealth of witty maxims, this collector’s item will keep you chic and happy for seasons to come, whether you pull it on with tailored black trousers or a beat up pair of boyfriend jeans.