I'm going to be honest here and admit that I've actually never worn heels with dresses. I'll include the mule or block heel in there once in a while but I think there are other styles that not only are more comfortable but simply make your dress look ten times as cool and elevated. If you're used to wanting to throw a pair of stilettos or pumps on with your dresses and want to change it up but don'tknow where to start, I'm here to help. It's my job to, after all.
Below, I've listed 7 shoe styles that I always count on for pairing with any kind of dress from flowy maxis to silk slips. Whether you tone your dress down to the more casual side with a pair of converse or have knee-high boots that’ll complement your ensemble, your outfit will still feel complete even if you aren’t wearing heels. See for yourself below.
You can never go wrong with a pair of classic chucks—I wore them in middle school and you'll still catch me wearing them today. They pair well with longer lengthed dresses that hit at the ankle.
Even if you're wearing cowboy boots underneath a long dress, just the sharp pointed toe already adds a cool-girl element to your fit. I personally love the taller versions, but the shorter ones are growing on me slowly.
Back when vacations were a thing, dad sandals were all I wore with dresses. I haven't found a shoe that beats the comfort level on these.
If you're looking to add a little edge to your look, this is the way to do it. I love the juxtaposition of a chunky stomper boot with a feminine dress.
I didn't think this one through till recently when I spotted chunky loafers all over the fashion scene and thought I'd give it a try with dresses. SInce they're usually paired with more structured pieces, I think they add a contrast to the flow of a dress.
If you still want a dressed-up element with a heel, I'd recommend a strappy sandal over a stiletto or a pump. They're comfier than they look, and they're clearly very loved by fashion girls everywhere.