The 5 Pairs of Shoes I’ve Worn Countless Times Since January 1

Twenty-twenty has been a weird year, to say the least. There are many, many things we’ve done differently this year: Spending most of our time at our homes, living on Zoom calls, and using terms like “social distancing,” just to name a few. Another thing we’ve done very differently the past 12 months is the way we’ve been getting dressed. I don’t know about you but I’ve been living in the same cozy outfits because putting on anything else just feels wrong. 

That’s especially true when it comes to footwear (what are heels again?). I’ve essentially spent the entire year in the same five pairs of shoes and completely neglected every other pair in my closet. Not only are they comfortable, but they all pair well with all the laidback outfits I’ve been rotating through this year. From the comfortable sneakers I’ve worn daily to my chunky boots that go with every outfit, below are the five versatile shoes that I’ve been living in this year—and I’ll probably continue to do so in 2021. 

Obviously, 2020 has been a year like no other, which has also meant my shoe choices have been like no other. Truthfully my Ugg slippers have been my most worn shoes this year because staying home means staying comfortable. The backless nature of these ensures your feet don’t get too hot inside the shearling (even in L.A.) so I wear them year-round. And although we don’t know what 2021 will look like yet, these are a worthy investment you’ll wear for years. Trust me—they’re money well spent. 

I’ve owned these sneakers for years (as you can tell by how beat up they look—don’t judge) and have never gotten more wear out of them. Since trading in my typical heels for more comfortable footwear this year, my Stan Smiths have been on heavy rotation almost every time I leave the house. They’re comfortable, classic, and go with everything, making them my go-to pair these past few months. 

I’ve owned these Dr. Martens for a few years now and can honestly say they come back season after season. They keep my feet warm and protected when stepping out during the fall and winter, plus they look great with jeans. Chunky boots are also a huge trend this year and this is a relatively affordable way to get in on the trend with a pair that will last you for years. 

Long walks have become my workout activity of choice since my usual HIIT class wasn’t an option, and they’re one of the things I’m going to keep in my routine once life goes back to normal. I always feel grounded and clear-headed after a stroll around my neighborhood, and my Nike running shoes are the only pair I’ll wear as they’re easily the most comfortable workout shoe I own. 

Although I wasn’t getting as “dressed up” as I normally do this year, there were still occasions with friends or date nights with my boyfriend where I wanted to feel put together without overdoing it. For these, I turned to these Iro ankle boots that feel polished yet relaxed enough to wear in my house. I love that they have a small block heel and the chic nude color goes with everything. Oh, and the leather is buttery soft. 

You can never have too many pairs of slippers.

I’ve heard great things about APL for years so I’ve been eyeing these for a while—and since I’ve been wearing my running shoes so much this year it might be time to invest in a second pair. 

The chunky boot trend isn’t going anywhere, and these are the kind of shoe you’ll wear for years. 

A good pair of neutral slides is a must. 

I love the minimalist look of these sneakers.

These affordable combat boots were a Prime Day favorite for Who What Wear readers.

Up next, six color pairings that always make me think “wow.”