10 clothing items people couldn’t stop wearing in 2020

favorite clothing items of 2020 fashion
Stylists, bloggers, and editors told Insider what clothing pieces they reached for the most in 2020. Gianluca Russo; Kemi Ajibare; Courteney Larocca
  • Throughout 2020, people leaned on fashion for comfort and functionality.

  • Insider spoke to editors, professional stylists, and bloggers about the clothing items they reached for the most throughout the year.

  • Some of their favorites were nap dresses — an elevated version of a nightgown — as well as relaxed-fit jeans, matching loungewear sets, and colorful leggings.

  • Visit Insider’s homepage for more stories.

While the year 2020 was filled with unprecedented challenges, people continued to experiment with fashion.

For some, trying out new styles (or reverting to nostalgic ones) offered a distraction and a creative outlet. Earlier in the year, people tie-dyed their clothes en masse, and celebrities and influencers inspired people to turn pillows into dresses as part of a whimsical social-media trend.

For many, this year may have also sparked a need for video-call-approved loungewear pieces or realizations about the power of dressing up, even when you don’t have anywhere to go.

As 2020 comes to a close, Insider spoke to editors, professional stylists, and bloggers to find out what clothing items they couldn’t stop wearing this year – and that will likely continue to be their closet essentials.

Editor’s note: Prices and links to clothing have been provided where available at the time of writing.

Fashion writer Gianluca Russo said a lounge set from Rihanna’s Savage X Fenty brand was a must-have this year.

Gianluca Russo wearing Savage x Fenty
Gianluca Russo. Gianluca Russo

Gianluca Russo, writer and creator of the size-inclusive online community The Power of Plus, told Insider that his clothing picks of the year are the Savage X Fenty Smoking Jacket ($89.95) and Savage X Fenty Satin Pants ($64.95).

“Not only do they make working from home feel more luxurious, but I feel overjoyed to know that I’m supporting a brand that prioritizes size inclusivity for both women and men now. ” Russo said. “Every time I wear the set, I feel like my own personal version of Miranda Priestly, and what better feeling could I ask for from a pajama set?”

Insider’s style reporter said she couldn’t stop wearing a pair of Everlane bike shorts.

everlane bike shorts Celia Fernandez
Celia Fernandez. Celia Fernandez/Insider

Celia Fernandez raved about The Perform Bike Short ($38) from Everlane, which is available on the brand’s site in Black and Ink Grey at the time of writing.

“I bought the bike shorts in June and have been living in them ever since. Now that I’m six months pregnant, the shorts still fit perfectly and aren’t uncomfortable around my belly at all,” Fernandez said.

She continued: “They have a pocket on the inside so I can easily put my credit card or cash in it when I have to run down to the bodega quickly. I love that these don’t ride up, and they stay in place all day long and are soft to the touch.”

This year, one Insider editor discovered nap dresses, and she says she’ll continue to wear them.

courteney larocca nap dress favorite clothing piece 2020
Courteney Larocca. Courteney Larocca/Insider

Insider’s celebrity and music editor Courteney Larocca described Hill House Home nap dresses as comfortable and stylish, making them a favorite of the year that she’ll keep wearing in the future.

“I have never been one to spend more than $50 on a single clothing item without panicking, and so I surprised even myself when I got really into Hill House Home nap dresses this year,” Larocca said.

She continued: “They’re not all that cheap, but when I found myself spending money on absolutely nothing else, suddenly it didn’t seem that unreasonable to splurge on what is, essentially, a very cute nightgown. My favorite style is the Athena, but I’ve tried a few different ones, and they all make me feel instantly better after putting them on. They’re so stylish and adorable, yet so comfortable, that I find myself constantly wanting to buy more. The best part is I don’t see myself ditching them post-pandemic, either.”

The Athena Nap Dress ($100) from Hill House Home is available on the brand’s website, along with other styles in various colors and patterns, at the time of writing.

Podcast host Rachel Schwartzmann highlighted leggings from Girlfriend Collective as a wardrobe staple.

Girlfriend Collective leggings
Girlfriend Collective sells activewear items that are made from recycled and sustainable materials. Girlfriend Collective

“I’ve been a fan of Girlfriend Collective’s colorful selection of leggings for years. For me, they check the boxes in both style and wearability,” Rachel Schwartzmann, writer, founder, and host of “Slow Stories” podcast, told Insider. “I also respect their commitment to sustainability.”

Girlfriend Collective’s leggings are available in a variety of colors and fits, including the High-Rise Pocket Legging ($78), pictured above, as well as maternity styles.

Baggy “dad jeans” were a 2020 favorite for personal stylist and blogger Kemi Ajibare.

Kemi Ajibare favorite clothing item 2020
Kemi Ajibare. Kemi Ajibare

Stylist Kemi Ajibare, who goes by @StyledByKemi online, said her most-worn clothing item of the year was a pair of Topshop Ripped Dad Jeans ($80), which are available online at Nordstrom.

“This is what I would call an elevated basic. I am an avid denim lover, and dad jeans have been my absolute favorite of 2020,” Ajibare said.

She recommends this style for anyone who likes jeans with a relaxed fit.

Cozy slippers with a sturdy sole were one Insider editor’s essential shoes of the year.

jcrew factory slippers
J.Crew Factory slippers. J.Crew Factory

Freelance editor Paige DiFiore said that she can’t stop wearing a pair of J.Crew Factory faux-shearling slippers ($29.50) that she bought this year.

“During a sale, I ordered these soft moccasin slippers, and I haven’t stopped wearing them. They are incredibly soft and cozy,” DiFiore said. “Plus, I don’t have to worry about them sliding off, as is the case with many backless slippers. Because the sole is so thick, I can also wear them in a pinch to walk to the mailbox or take out the trash without having to dig out a pair of sneakers.”

Stylist Laurie Brucker loved dressing up a puff-sleeve T-shirt from the brand Joie.

favorite clothing items 2020 stylist laurie brucker
Laurie Brucker. Laurie Brucker

“This simple T-shirt offers me the fun and the fashion of the puff sleeve with the comfort and ease of a T-shirt,” Laurie Brucker, professional stylist and author of the forthcoming book “You are the Style!”, told Insider.

“It’s perfect for quarantine-chic,” Brucker continued. “I dress the shirt up for work, I dress it down for home, and I even dress it ‘creative-cool’ as a mom on the go. I love that it makes any outfit look effortlessly stylish without trying hard.”

The Joie Artemesia Puff-Sleeve Top ($39.60) in the same color is sold out at the time of writing, but a darker shade is available at Saks Fifth Avenue.

One Insider editor fell in love with a matching set from Loft’s Lou & Grey collection.

lou and grey matching set
Similar sweats from Lou & Grey in the shade Brilliant Copper. Loft

In September, deputy editor Chloe Pantazi purchased Lou & Grey’s Signature Softblend Sweatpants ($59.99 – $69.99) and matching Sweatshirt ($69.50), which are available at Loft.

“It’s getting me through the cold months,” Pantazi said of the matching set. “I usually wear the sweater and sweatpants together (I got them in Brilliant Copper, a shade that felt appropriate for the fall), but they also work well with most of my other work-from-home attire.”

She continued: “The set makes me feel somewhat put-together and presentable enough for virtual meetings, but always cozy. I’m a big fan of the slightly fuzzy lining inside, and I’ve worn the set so much I have my eye on the same item in other colors.”

Fashion blogger Sarah Tripp called Lululemon’s Align leggings her favorite pants for everyday wear.

sarah holiday lululemon 10.JPG
Sarah Tripp. Sarah Tripp

“I love my Lululemon Align leggings,” said Tripp, who goes by @sassyredlipstick on Instagram. “They are so soft and comfy, and I can wear them working out or day-to-day as athleisure. They’re easily my most-worn clothing item of the pandemic. Plus, this year, they now extended to a size 20, which is great for more size inclusivity.”

Leggings in Lululemon’s Align collection retail for between $88 and $98 at the time of writing, depending on the length and style.

Another Insider editor said she can’t believe she ever went a winter without this pair of quilted waterproof boots.

boots winter favorite clothes of the year
Lydia Warren wearing Bogs’ Women’s Snowday Tall Boots. Lydia Warren/Insider; REI

Insider’s senior distribution editor Lydia Warren described her pair of Women’s Snowday Tall Boots from the brand Bogs (which are on sale for $89.73 at REI at the time of writing) as a must-have.

“Every time I wear them, I can’t believe I ever lived without them,” Warren said. “Considering this was the Year of Comfort Clothing, I decided to go for feel and ease of use over aesthetics, and it was a very wise decision. They are waterproof, warm, not too clunky, and I don’t even have to do up laces. And they arrived in advance of the snowstorm!”

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