Certain seasons are challenging to dress for. Winter is easy peasy, as is fall; just throw on some denim pants, a thick sweater and boots, and you're good to go (as long as you remember your coat).

This orange-and-white striped dress is available in sizes X ... or other sunny event in the tasteful Merokeety Sleeveless Sweater Dress, currently 61% off at Amazon.

Or you can swap a basic tee for a breathable, knit short sleeve or striped polo sweater. Or even an intricately-stitched ...

Wear it with jeans or dress pants when temperatures take a dip. 9. Yacht Wife: Everything about this drapey striped sweater screams luxury. Try half-tucking it into a maxi skirt to nail rich mom ...