Tip #4: Sure, wear them with a dress or skirt, just be careful.

Admittedly, this is almost painful to write, as I just can’t help but conjure up the sight of long skirts, socks, sneakers and fanny packs. But a thoughtful approach to elevate the style of the sneaks and be modern and playful to boot CAN happen. Just look at that photo above! But be careful, okay? It’s harder than it looks to showcase this skirt + sneakers look without looking like a 1980s secretary. Tips for how to accomplish this look are found in the captions below.

Tip #5: Grab a couple pair and some of those low-rider socks

It’s summer, and there will be times you will welcome not showing off your pedicure, which needs some work. A closed-toe slide or two or a sneak that makes you happy will be a welcome relief from flip-flops and such.