The Eight Best Sandals To Wear With Dresses

I had to start with these because, well, I’m featuring these sandals in all of my pictures! I love a good pair of block heels. It’s a sandal that has been around for a long time, but I feel like it was revived a few years ago and everyone went crazy for them. For a good reason too. Because of the block heel, the sandals are incredibly comfortable, but still have the polished look of a heel.

When they have a wooden block heel, they can be worn a little more casually, (or dressed up). But when they’re sold in one material, they have a much more dressed up look.

I own the sandals (pictured here) in three or four different colors because of how versatile they are. I originally bought them at J.Crew Factory, but they’re available all over the place now.

The ultimate fancy sandal, right? A high heeled sandal is the perfect pair of sandals for any dressed up occasion when you need something to pair with a nice dress. Personally, I don’t really dip my toe in this pond unless I have a nice event to attend, but summer is the time for weddings, right? I love wearing ankle strap high heels with midi or maxi dresses. They pair great together for any wedding guest look. They help to elongate your legs which will instantly make any dress look better. I try to aim for under $75 with these shoes, since I know that I’m not going to get as many wears out of these heels. (If I’m going to wear any heels to the office, it would be heel pumps.) I have examples below of some great under $75 options.

A wedge is perfect when you want you want to look a little dressed up, but the occasion isn’t fancy enough for a stiletto. It’s a great sandal though, because it’s looks excellent with almost every dress AND it’s incredibly comfortable. Honestly, a wedge is the “do it all” sandal you need to have in your closet.

Why not jump from the fanciest sandal to the least fanciest? Though, I guess a flip flop could really go either way depending on what you get and how you wear it. Are you getting the Old Navy $2 rubber flip flops or the Jack Roger $125 flip flops? Big difference in price and look. These are probably the most versatile of all sandals not only because of what I just said, but also because you could wear them with anything from a pair of shorts to a dress and still look good.

Flip flops with a dress will give you that casual breezy look we’re all aiming for, like you’re up for anything at any moment (okay, I’ve been listening to the “Be There in Five” podcast for too long, lol). But really, even if you do have the fanciest of flip flops on, they really do give the impression like you’d be up for lawn games at any moment, you’re not the stuck up girl in heels at a backyard party. Wield that power wisely.

Slide sandals are the cooler younger sister of flip flops. They say that “I put more thought into my outfit and I’m far less likely to injure foot when I STILL trip over the curb because wearing cuter shoes didn’t make me less clumsy.” Even when they’re rubber, they still look cuter (we’ll discuss that later). Everything I said above about flip flops applies, but with a shiny gleam. Even Jack Rogers agrees, because they turned their legendary flip flop into a cooler slide version. Slide sandals can also be more easily paired with date night dresses when you want to look cute, but wherever you’re going is too casual for heels.

The strappiest of all strappy sandals? The sandals not for the lazy? I have a love hate relationship with these shoes. I love how they look when I see girls wearing them with short breezy dresses but I hate the idea of putting them on myself. Though, back in 2017, I got a shortcut pair that all you had to do was zip them up the back, which was super easy. They looked (well, look, I still have them), so cute with loose, above the knee dresses. Even when you have strappy sandals that go all the way up to your knee, I think they’re the best with shorter dresses, because then your legs don’t get cut off anywhere and you’re still able to give illusion of long legs, no matter how long your legs are!

Okay, just a warning, they can also make your feet look long (see this example from Free People). So try on a few pairs before you commit.

Remember that period in the late 90s, early 2000s when Birkenstocks became really cool again? We all got to experience what arch support was like before we really knew why it was important or that we desperately needed it? Well, I’m voting strongly right now to bring that back. I can’t afford the actually brand, but I got a similar pair recently with the same arch support and built in padding and OH MY GOD, my feet love me so much more every single time I put them on. It’s like walking on little clouds. I volunteer to run errands just so I can wear them. Even better, they pair perfectly with t-shirt dresses. I would have never thought it, but I love their look with tee dresses and other casual dresses. It’s a match made in comfort heaven.

I said I would get to rubber slide sandals and now I’m here. I got my first pair last summer and they are a game changer. There have already been plenty of blog posts on here praising them, so let’s stick to the dresses they work with. Like Birkenstocks, I love pairing them with casual dresses. Tee dresses and looser maxi/midi dresses have basically been my jam with this pair of shoes. They’re a great anytime shoe because they’re so comfortable and they come in so many colors and patterns. Plus they’re rubber, so I can wear them in the rain, which is perfect. I’ve worn them to the beach AND just walking around. They’re the “do it all” shoe.