Elizabeth and James motorcycle leather shorts that I have worn an absolute ton. I paired them with opaque tights and knee high flat boots, and am happy that now that the weather is warmer I can still wear them, but with bare legs, a floral top and shoes with a bit of an edge, like a black Roman sandal, wedge sandal or embellished flats.
Shorts can be tricky. I think the super short styles are best left to a younger woman or for the beach, but frankly it kind of depends on where you live & of course your body type. A rear view peek before you leave the house can give you a reality check, should you need it. As always, fit and proportion matter.
Remember "walking shorts" as they were called in the 80's? How about "pedal pushers"? Bermudas? If you do, then choose carefully before you put a pair of shorts that hit behind the knee--because I have to be honest here--longer doesn't always mean more flattering--and you could end up looking frumpy. If you are more comfortable in longer styles, make sure your top is flattering, a flowing blouse or tee--and cute flats. I am not a fan of those tight denim knee length shorts--I think they look good on no one. I will make an exception with the Hudson Jeans Viceroy Stretch Shorts--(in white), these have an incredibly flattering fit and looks awesome dressed up with a wedge. Or you can always roll the legs a couple of times for a more casual look with your favorite flip flops. And watch the pleats, sister. My leather shorts have pleats but they don't make me look like I am ten feet wide, they just make the fabric (or in this case, leather) lay right.
My favorite look in shorts this season--a white short with a floral top, cuffed paperbag styles, leather shorts with a sequin tee and a classic camel colored short with a funky sweater. The deal breaker on taking shorts from basic casual wear to chic outfit? The shoes. Come on, show us your gams girl!