Shoes That Will Kick Your Outfit Up a Notch (and Not Kill You in the Process!)

Have you ever been the victim of super-uncomfortable shoes just for the sake of a killer outfit? Well, it’s 2021, and we’re not doing that anymore! We’re having our cake and eating it, too, meaning we’re shopping for shoes that are both stylish and comfortable. Before we get started, let’s talk shoe shopping 101.

Get the Right Size

We cannot stress this enough: When shopping for shoes, it’s important to try on different sizes to see what feels best. Shoes that are too small will bring you nothing but discomfort, while shoes that are too big will have you clomping around, feeling insecure about your footing.

Consider the Heel Height

Know what threshold you can handle when it comes to heel height. If you can strut your stuff in a 4-inch stiletto, go for it! But don’t force yourself into a shoe you feel you can’t steadily walk in.

Check the Cushioning

A little bit of cushioning or padding in the right spots can make all the difference when it comes to the comfort of your feet. Again, take the time to try on different styles and experiment with insoles.

Now that we know some general shoe shopping rules, let’s talk about specific styles that are both trendy and comfortable.


Platform shoes are having a moment right now, and they are our top choice for both comfort and style. The secret is in the angle of the shoe: Platforms elevate your entire foot, making them easier to walk in versus your everyday heel.

Our Pick: The Forever Platform Sneaker from Everlane ($70, shop here)

Block Heels

The block heel is another trending shoe style, which is great news if you love how classic high heels look. Block heels are more comfortable than thin heels because they provide more stability through even weight distribution. Block heels are unique enough that they can act as an accent piece, giving your outfit a touch of retro-chicness.

Our Pick: ASOS Design Profile Chunky High-Heeled Loafer ($50, shop here)


Is anyone else surprised by this clog revival? We aren’t sorry, though, because they are both cute and comfortable! Clogs that buckle around the ankle tend to offer more support than those that slide on, and they won’t alter how you walk in them.

Our Pick: MIA Shoes Abby Clog from Free People ($109, shop here)

Retro Sneakers

You had to know we would include sneakers on our comfy shoe list. Nike, Adidas, Reebok, and New Balance are all revisiting and revamping retro styles these days, and we love them because they are designed with comfort in mind and can add juxtaposition to any outfit. Whether it’s a dainty maxi skirt or an all-black business-casual look, a retro sneaker will be the epitome of style and comfort.

Our Pick: New Balance 237 Sneaker ($74.99, shop here)

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