I Found 6 Comfy Heels You Can Wear for Hours on Valentine's Day

Shop my picks from Vivaia, Calvin Klein, and more.

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I'm Shopping These 6 Comfy Heel Styles I Can Stand and Dance In All Night for Valentine's Day

Amazon / Nordstrom /Vivaia / InStyle

February is one of my favorite months of the year. I never need an excuse to show extra love to those around me, but when it comes to Valentine’s Day, I go above and beyond. I have tons of dinners and gatherings slotted on my calendar for the month and I plan on doing everything from dancing at jazz clubs to cooking three-course meals, I have to be dressed to the nines while doing so. I already have my dresses ready to go, and the only thing I have left to do is find a comfy pair of heels that can keep up. 

I rounded up six comfy styles from Vivaia, Dream Pairs, Calvin Kelin, and Naturalizer that have cloud-like insoles, spacious toe boxes, and chunky block heels that will make walking and dancing the night away a breeze. And prices start at just $37.

6 Editor Picked Comfy Heels:

  • Dream Pairs Close-Toe Block Heels, $37; amazon.com
  • Dream Pairs Platform Mary Jane Heels, $44; amazon.com
  • Calvin Klein Dainty Kitten-Heel Pointed-Toe Slingback Pump; $99; nordstrom.com
  • Naturalizer Jayla Half d'Orsay Slingback Pump Heels, $125; nordstrom.com
  • Vivaia Julie Pro Round-Toe Chunky Heels, $139; vivaia.com
  • Vivaia Aria Pointed-Toe Block Heels, $139; vivaia.com

Dream Pairs Platform Mary Jane Heels 

DREAM PAIRS High Chunky Platform Closed Toe Shoe


Buy on Amazon $44

If you have a Valentine’s Day look that calls for a bit more oomph than a simple pump, I would suggest Dream Pairs Platform Mary Jane Heels. They look so darling with a pair of socks, but also can be styled alone with a chic little black dress. The heels come in five colors: matte and shiny black, red, navy, and white, and are available in sizes 6 through 11. 

They feature a chunky 3.7-inch heel and a nearly one-inch platform for added stability and comfort to walk in. It has a thick ankle strap with a buckle so the shoe stays securely on the foot, a spacious square toe box, and added padding at the back of the ankle so the shoe doesn’t chafe against the skin or flip off when walking.

Calvin Klein Dainty Kitten-Heel Pointed-Toe Slingback Pump Heels

Calvin Klein Dainty Kitten Heel Pointed Toe Slingback Pump


Buy on Nordstrom $99

My go-to shoe for when I want to be comfy on my feet for hours, is a pair of kitten heels, so when I came across these Calvin Klein Dainty Kitten-Heel Pointed-Toe Slingback Pump Heels, I knew I had to add them to this list. They come in light blue, neutral, black, and ivory, and are available in sizes 5 through 11. It features an elastic slingback design that just slips on around the ankle, a pointed-toe box, a short 1.75-inch heel, and a plush insole for added comfort.

Vivaia Julie Pro Round-Toe Chunky Heels

Round-Toe Chunky Heels


Buy on Vivaia.com $139

Being a fashion editor, I’ve tested a ton of different heel brands, and the brand that has never failed me in terms of comfort is Vivaia. My go-to style that is easy to dress up and down is the Julie Pro Round-Toe Chunky Heels. They come in 10 colorways including black and beige, beige and tan, and navy and beige, plus the size ranges from size 5 through 11. 

It has a spacious round-toe box, an ultra-plush diamond padded insole I can effortlessly walk and dance in for hours, a block 1.7-inch heel, and rubber outsoles for added traction on slick surfaces. The heels even have a blister-proof pad at the back heel to minimize rubbing and chafing. These were made with comfort in mind.

Shop more comfy heels for Valentine’s Day, below.

Dream Pairs Close-Toe Block Heels

DREAM PAIRS High Chunky Closed Toe Block Heels


Buy on Amazon $37

Naturalizer Jayla Half d'Orsay Slingback Pump Heels

Jayla Half d'Orsay Slingback Pump


Buy on Nordstrom $125

Vivaia Aria Pointed-Toe Block Heels

Pointed-Toe Block Heels


Buy on Vivaia.com $139
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