As you’re probably aware, shoes can make or break an outfit, but that doesn’t mean you have to play it safe when dealing with outfit-and-shoe combinations. Oftentimes the best pairings are the most outside-the-box ones. And we looked to some of the chicest women around (and on Instagram) to bring you 11 examples of outfit-and-shoe combos that make you look like you know what you’re doing (regardless of whether you do or not, sartorially speaking).
So what does looking like you know what you’re doing even mean when it comes to an outfit? As you’ll see among the looks below, it’s choosing a shoe style that’s a bit unexpected but still complementary. The shoes you choose say a lot about your personal style, how good of an eye you have, and how much you know about current trends.
Now that you know, read on for the outfit-and-shoe combos that’ll make you look like you know what you’re doing, and shop the shoes you’ll need to create them.
Pair rugged combat boots with something flirty to look especially of-the-moment. 
The prettiest shoes to wear with jeans and a tee? Embellished ballet flats. 
Minimalist, strappy heels will make you look taller when worn with a jumpsuit. 
When wearing denim-on-denim, choose a shoe style that matches the chill vibe (i.e., Converse high tops). 
The coolest way to wear a pretty dress is to choose a shoe style that contrasts like “ugly” sandals. 
The hands-down easiest way to look cool this summer is to wear a black jumpsuit with espadrilles. Done and done. 
If you really want to look like you know what you’re doing when it comes to red shoes, treat them like a neutral and wear them with your rainbow brights. 
Let the sneakers take center stage this summer and keep the rest of your look simple. 
Sock boots can be tricky with jeans and trousers, so stick to a midi skirt that shows them off. 
Leopard print is undeniably bold, so keep your shoe style understated yet cool with a pair of slingback kitten heels. 
Next up, the out-of-the-box outfit It girls are wearing.
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