What items do you define as quintessential summer pieces? Maybe your list includes the perfect vacation dress? A trendy swimsuit? Or even a woven bag? No matter what’s on your list, it’s likely that each item has gone through a rigorous litmus test to make the cut. Sure, everyone may not spend copious amounts of time debating what’s the best footwear for summer. Still, it’s pretty common that a few slit seconds are spent thinking about what feels apropos for the season—e.g., putting on sandals may feel like a “better” footwear choice for a summer day than a pair of ankle boots.

Like it or not, we always return to our lists to help us navigate getting dressed every day. But, what if I told you that “practical” staples list, those everyday calculations are limiting your sartorial expressions? The beauty of a new season isn’t that you’re swapping out staples or buying recent trends; it’s the ability to see your closet with fresh eyes. Summer is an opportunity to take your most cherished items and make them feel brand new through styling. Because if you can’t wear your clothing year-round, what’s the point?

Of course, that’s easier said than done when you’re used to adhering to suggestions that you “shouldn’t” wear specific items in the summer—ahem, ankle boots, for instance. It’s not impossible, though, to break the rules. So, in an effort to prove that any “off-season” item can be relevant with the proper styling, I’ve rounded up 16 summer outfit ideas that show how to wear ankle boots in the summer. Whether you’re hoping to reboot your seasonal staples list or need simple outfit formulas to copy, these ensembles will push you to step outside the box.