Denim shorts are always cute and comfortable. Their tendency to look casual isn’t always a plus, though. Wearing denim shorts to work is only appropriate for a very few offices, and they’ll never look right at an upscale restaurant, but with careful styling and some wardrobe staples, you can dress these shorts up or down to suit a wide range of activities and moods.
Faded cutoffs will never look polished, but you can dress up dark denim shorts for a summer date night or casual meeting. Choose shorts that hit at the knee or a few inches above and wear them with a thin tank top and a jacket. The tailored jacket of a business suit would probably look too formal, but a fitted blazer or collared cotton jacket — preferably with three-quarter or rolled sleeves — makes this outfit look “dressed.” Pair this ensemble with sleek hair, metallic jewelry and loafers or strappy platform sandals.
For drinks with the girls, wear your denim shorts with a silky top. Shorts with a rolled hem look appropriately polished. Unless the weather is really sultry, choose a top with short or long sleeves; a skimpy tank top paired with shorts can look too bare or beachy. Opt for a patterned, jewel-tone blouse if you crave color or choose a simple white or black shirt if your style is more classic. Wear the shirt loose or tuck it in just a bit at the front. Wear your hair down and add flat strappy sandals or sleek booties and a few pieces of bold jewelry.
Mix faded, mid-thigh shorts or slouchy cutoffs with a casual top to evoke a sunny ’70s style without looking like you belong at Woodstock. Pair your shorts with a short-sleeved white lace or eyelet top or choose a printed or embroidered tunic. Be sure that any tunic you choose hits at least several inches above the hem of the shorts. Wear your hair loose and add beaded jewelry or a hat with a floppy brim and finish the look with flat sandals.
A beach-casual look makes you feel light and summery even if you’re landlocked on a cloudy day. Wear loose shorts or cutoffs with a floaty sleeveless top or a printed T-shirt. In cooler weather, top a tank with a thin, loose-knit sweater or an unbuttoned, oversize denim or chambray shirt with rolled sleeves. Wear your hair in a ponytail or messy bun and add bright jewelry and leather flip-flops.
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