LITTLE MISS SUNSHINE – With its Peter Pan collar, cap sleeves, and delicate pin-tucked bodice, Lorick’s brilliant yellow silk crêpe dress, paired with ballet flats and delicate jewelry, could easily just play nice. But why stop there when bronze platform gladiator sandals and a thick stack of bangles can step things up for this otherwise street frock? LORICK DRESS, FRANCES MAY; STEVE MADDEN SANDALS, NORDSTROM; PLASTIC BANGLES, IMP

FLIP SIDE – Because nobody ever said that handsome and sense of humor couldn’t coexist: Ben Sherman’s navy pin-striped shirt comes with a tie that’s cut from the same cloth. Its skinny shape lends a punky feel that’s anything but buttoned-up. SHIRT AND TANNER BELT, BLAKE; KASIL JEANS, NORDSTROM; WESC HEADPHONES, LOCAL 35

CONCRETE JUNGLE – Gym-issue gray fleece graduates to the next level when Triple Five soul cuts it into a shaped, strapless dress. Here, graffiti-splashed sneakers and a sporty jacket deliver a streetwise effect, but the simple chemise could just as readily go uptown with a leather jacket and heels. DRESS, WESC WINDBREAKER, UMBRO PRINT HIGH-TOPS, LOCAL 35; ZODIAC DIVE WATCH, NORDSTROM; SILVER HOOP EARRINGS, GYPSY CHIC.

SUMMER OF LOVE – A Moroccan-inspired print gives Tola Layla’s cotton shirtdress a sense of Beat-era cool. Engraved metal cuffs and yellow-lensed aviators complete the breezy effect. Later, take the look into evening by slipping on a khaki canvas jacket and tall boots in a similar hue. TOLA LAYLA DRAWSTRING DRESS, IDOM; AVIATOR SUNGLASSES, GYPSY CHIC; ENGRAVED METAL CUFFS, IMP.

THE LAST DETAIL – Summer fun means smooth sailing in Samantha Pleet’s cheeky hooded romper. Anchor a saucy look with a shape-defining belt, white leather plaforms, and a boyish cap. Or for effortless charm, wear the linen all-in-one with flat sandals and a cropped jacket. ROMPER, FRANCES MAY; STEVE MADDEN SANDALS, NORDSTROM; TRUTH COTTON BELT, OLIO UNITED; BRIXTON CANVAS CAP, LOCAL 35

WHITEOUT – Strip down to the basics in a white bandeau bikini accented with tiers of tiny ruffles. BCBG SWIMSUIT, NORDSTROM