Skip to main content

What To Wear When: A Back To Work Men’s Fashion Guide for 2021

After a year or more from working from home, trying to figure out what to wear in an office setting can be a nightmare. We swear getting dressed used to be a lot easier. So if you find yourself standing in your closet wondering what the hell you’re going to wear to work, we promise you’re not alone.

Men’s fashion has been more or less on pause for the past year, and we’re guessing there are a lot of guys who could use a back-to-work style guide. So to help you, and ourselves, dress appropriately for the workplace after so many months of dressing for Zoom, we decided to consult some experts.

In this article, we’ll discuss what to wear when heading back to the office in 2021.

  • How to incorporate the athleisure trend into work clothing
  • Essential menswear items to expand your work wardrobe
  • Office wear dos and don’ts
  • The men’s accessories you’ll need
  • Two business casual outfits created by men’s fashion influencer Nate Ma, aka @Cuffington

For this men’s fashion guide, we consulted Sharon Graubard, the founder and owner of MintModa. Graubard is a fashion trend forecaster whose expertise has been quoted in publications that range from The New York Times to WWD.

In our interview with Graubard, he told us about a friend who works in finance. Before the office reopened, he and his co-workers received a “dos and don’ts” dress code email. (Because, again, everyone is struggling to get dressed post-pandemic.) The list of what to wear included “collared shirts, particularly wovens like poplin, with knitted polos as a more casual option. They also were instructed to wear slacks, tailored chinos, or un-distressed jeans.” Dress code emails from work are helpful, but not everyone gets them. That’s why we tapped two fashion experts who can navigate the workwear minefield with ease. The aforementioned Graubard was the first, and the second is men’s fashion influencer and photographer Cuffington. We highly recommend you follow his Instagram, where his 110K followers pay careful attention to his style how-to videos and sartorial advice.

Related Stories


View this post on Instagram


A post shared by Nate (@cuffington)


1. Prepare To Make a New First Impression

Before we even talk about what to wear when going back to work, you need to remember that you will be in an office with people you may not have seen in months, or that you’re meeting for the first time. So here’s a bit of uncomfortable advice for you: people will 100% make snap judgments on your effectiveness in the workplace based on how you present yourself. Those judgments may be unconscious, but they’re happening.

Your new fit should instantly remind your bosses and co-workers that you’re responsible, reliable and on top of your game. Believe it or not, doing that can be easy. Graubard says “make sure your clothes are fresh and clean. ‘Intention’ is the key word. Put your clothes on consciously, don’t just throw on whatever is on the bedroom chair. Look critically in the mirror.”

Graubard has another piece of confidence-building advice. “Look in the mirror and dress like you mean it.”

Before you leave the house, give yourself a close look in the mirror and ask yourself, “What does this outfit say about me?” Does it say, I’m someone worth taking seriously, or I don’t know what I’m doing here?


2. Can You Wear Athleisure in the Workplace?

Not too long ago, we discussed how workout clothing has evolved into athleisurewear, which became absolutely ubiquitous during the pandemic when style was all about comfort. Working from home, we lived in our comfy joggers and favorite t-shirts. Now that we’re going back into the office, athleisurewear fabrics have moved into more structured clothing that looks slightly less casual without sacrificing comfort.

“Many companies have started blending spandex/stretch materials (Polyurethane/Elastane etc.) into their clothing lines,” said Cuffington in an email interview. “Now you can enjoy the stretch comfort of sweatpants in denim, chinos, and even dress pants.”

Graubard has a few shopping pointers to help you look professional and polished at the same time. “Look for quality (when buying clothing). Fabrics that are too thin, or too stretchy, or textured like terry, might not give the professional look you’re going for. I noticed some of the streetwear brands are showing activewear silhouettes in wovens rather than knits, giving the pieces a more polished look… In general, woven (items) look more polished.” Confused as to what’s a woven fabric and what’s a knit? A tee or sweatshirt is a knitted fabric, while a woven fabric would be used in a dress shirt, jeans, or a bomber jacket.

Graubard agrees that you can wear athleisure wear to work, but don’t go overboard. “It’s a good idea to wear just one piece of activewear and mix it with more tailored pieces. (For example) a sleek woven windbreaker can work for casual or professional looks.”


View this post on Instagram


A post shared by Mack Weldon (@mackweldon)

Remember: Pulling off the athleisure look at work is all about cleanliness and confidence. If you pair joggers with a wrinkled tee or scuffed-up shoes, you’re not going to impress anyone. Before you head back to work, get rid of clothing that’s seen better days. If items are stained, faded, wrinkled beyond redemption or falling apart, dump them. Likewise, we know that during the pandemic a lot of people lost or gained weight. Cuffington suggests that you “double-check your suits and outfits to make sure that they’re not too tight or too loose. If they are, it might be time to buy a different size, or get your clothes altered by a tailor.”


3. Menswear Style Inspiration for Going Back To Work

Looking for specific recommendations? We’ve got some complete outfits below, but first we wanted to provide some basic men’s fashion inspiration to give you a genearl idea of what to wear when going back to work. We tried to provide a mix of more formal and casual fits. Right now, men’s business-casual clothing has been heavily influenced by athleisure.

Polo Ralph Lauren Slim-Fit Stretch Chinos

Look, if you’re struggling to get dressed, then keep it simple. These slim-fit black chinos from Polo Ralph Lauren will go with pretty much any outfit you can imagine, while also being comfortable and effortlessly stylish. They’re not too skinny to get you the side-eye from Gen Z, and they have enough stretch to help you wean yourself off joggers and sweatpants. Cuff them up and wear them with white sneakers of your choice, or pair them with some new men’s dress shoes for a fancier fit.

Lazy loaded image
Courtesy of East Dane

Napajiri Logo-Print Windbreaker

Made from polyamide, this lightweight front zip windbreaker manages to straddle both the techwear and the athleisurewear trends. Because of the simple design, it’s easy to toss on when going to work or when hiking on the weekend. It hits all the details Graubard mentions above, and it’s both polished looking and functional. Heck, even the model looks like he’s ready to hit the morning commute to work.

Lazy loaded image
Courtesy of FarFetch

Scotch & Soda Indigo Blazer

Right now, we’re loving the menswear coming from the Dutch fashion brand Scotch & Soda, which has plenty of outfits for your back-to-work business casual attire. If you lived in tees doing the WFH ear, you can still wear them under the fluorescent office lights, but adding a blazer to your outfit will set you apart from the crowd. When picking out a tee, Cuffington recommends that you “make sure your shirt is clean and crisp. Solid colors and simple subtle patterns work best. A simple move like tucking in your shirt can really elevate your look. Throw on a nice blazer over it for extra style points.” A blazer can make track pants look business-like too. Spend some time trying on your athleisure pieces with a blazer and you’ll be pleased with all the “new” and on-trend work outfits you suddenly have.

Lazy loaded image
Courtesy of Scotch & Soda


Polo Ralph Lauren Tech Sweatpants

While you might’ve gotten away with wearing a button-up on top and shorts for Zooms, you can’t do that in the office… even if you have great legs. Cuffington reminds us that “coming back to the office doesn’t necessarily mean you should give up your comfortable style.” Love sweatpants? You can get that same comfort and a sleeker look when you wear sweatpants’ tastier cousin, the tailored jogger. Do wear a cleanly designed jogger and match them with a button-up or a blazer.

Lazy loaded image
Courtesy of East Dane

4. The Right Accessories Provide the Finishing Touch

When thinking about what to wear when going back to work, it’s the little things that can turn clothing from “basically okay” to “Instagram-worthy.” Graubard suggests investing in “scarves, whether a silk square, a cotton bandanna or knitted muffler, as a nice way to add color. For the wrist, a watch or smartwatch is a classic accent, or a chain, beaded or leather bracelet… a tailored tote, a small cross-body bag, or a sleek backpack in leather or nylon are good workday choices. Belts give a nice finished look, and a tasteful statement buckle adds personality.”

Billy Reid Accessories

Billy Reid is another one of our favorite menswear brands in 2021. The Alabama-based designer describes his clothing as “lived-in luxury,” and we think that’s exactly right. In addition to stylish shirts, pants and shoes, Billy Reid also has a line of men’s accessories that we think you’ll love. His new braided leather belts are perfect for business casual looks, and his pocket squares and bandanas are always worth a closer look.

Lazy loaded image
Courtesy of Billy Reid

Todd Snyder x Timex Q Reissue

The right accessory will draw the eye and earn you the compliments you deserve. We’ve been raving about the Todd Snyder x Timex watch collection for a while now, and this Timex Q Reissue is an excellent choice for your back-to-work style. The gold-tone watch and blue face has a bold and unique look, and this watch has a retro flair that we love.

Lazy loaded image

Tumi Alpha Bravo Barksdale Crossbody Bag

This leather-trimmed crossbody bag has a ton of outer and inner pockets. You’ll no longer fumble trying to find a commuter pass, office keys or credit card. It also has an adjustable strap. The crossbody bag is very in right now, and this all-black accessory will match any outfit.

Lazy loaded image
Courtesy of East Dane

5. Back To Work Outfits for Men

We asked Cuffington to help us create a what to wear when going back to work outfit, and he did better — he created two of them for us. Each outfit’s items can be mixed and matched, so it becomes a mini capsule wardrobe of four looks. He says they’re “versatile and classic business casual outfits that are extremely comfortable and clean. They can be worn to the office and to happy hour afterward.”

Outfit #1: Buck Mason Oxford, Hiroshi Kato Slim Jeans and Thursday Executive Dress Shoes

“You can never go wrong with a classic blue oxford button-up shirt. It’s a timeless shirt that pairs well with everything from dark denim or brown pants.” We completely agree. This clean and stylish fit comes from Buck Mason, a brand that should be a staple in your closet.

Lazy loaded image
Courtesy of Buck Mason

“Classic Dark Blue Denim but upgraded with 4-way Stretch Fabric. [They] look sharp and feel comfortable with the 4-way stretch selvedge denim.” Even though Gen-Z favors looser fits, Cuffington told us that he prefers the “slim-fit cut for a more fitted and put-together look.”

Lazy loaded image
Courtesy of Hiroshi Kato


We wrote about these new dress shoes when they were first released, and the Matte Black version is particularly impressive. That being said, a classic brown dress shoe is easier to style. “Dress to impress with this clean classic cap-toe lace-up dress shoe. Not like your typical dress-shoe, the brandy hand-finish full-grain leather looks sharp with dress pants but also looks good with denim and chinos.”

Lazy loaded image
Courtesy of Thursday Boot Co



Outfit #2: Buck Mason T-Shirt, Hiroshi Kato Chinos

Cuffington created a second back-to-work outfit that’s classically cool and equally comfortable. If you’re working in a creative environment, this could be your new work uniform.

“You can’t go wrong with a simple clean t-shirt. Made with slub cotton which is breathable and has a nice texture to it. [This] shirt features a curved hem for a more modern look. Add a nice light jacket or blazer to elevate the look.”

Lazy loaded image
Courtesy of Buck Mason

These classic men’s chinos have the extreme comfort and softness of sweatpants. They also come in a modern cut that features a slim-fit silhouette that’s not too baggy or tight. We like these chinos because you can wear them with sneakers, boots and dress shoes, and they come in a variety of colors.

Lazy loaded image
Courtesy of Hiroshi Kato

Outfit #3: Untuckit Performance Shirt, Bonobos Off Duty Pants, Gola Sneakers

If you’re still in need of more menswear items to add to your closet, we’ve thrown together one more outfit recommendation.

Call this the sneaky comfort outfit. Each item is athleisure-inspired. They were picked because like activewear, they have odor and sweat fighting tech fabric, but they look like regular office wear. If you bike to work, or your commute resembles a rugger scrum, no matter what happens to you on your way in, you won’t look it when you cross the threshold. And yes, you can mix and match pieces with what you’ve got in your closet.

First up, the shirt. Made with performance fabric, this Untuckit wrinkle-free button-up shirt features a blue floral print shirt. The fabric fights sweat and odor, won’t wrinkle and has the right amount of stretch.


Tailored like a chino, but it feels and moves like a jogger. The relaxed-fitting pant has an elasticated waist and four pockets. It comes in nine other colors too.

Lazy loaded image
Courtesy of Bonobos

You can never have enough white sneakers. These white on white canvas sneakers first debuted in the 70s. They were designed for professional badminton players, but they’ve been re-styled for the modern era but still retain their court shoe endurance.

*Some of the quotes in this article have been lightly edited for clarity and grammar.


The Best Men's Sweaters