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Can’t Figure Out What To Wear? Check Out Our Guide of Casual Outfits for Men

We’ve created a style guide for casual outfits for men to assist any guy who’s trying to figure out what to wear when working from home, going out on the weekends or going on a date. Look, Covid’s done a number on all of us in more ways than one. Dealing with lockdowns, worrying about friends and family, and having a severely curtailed social life has made us feel like every day is thirty years long. We’ve learned that what we put on can affect our moods, and if you change things up a bit, you can feel more productive, relaxed and heck, even more attractive.

This article is going to break down men’s casual attire into three manageable style tip sections:

  • Work From Home
  • Weekend
  • Dating

From there, we’ll give you a few options for each part, so you can feel confident going into your next date, weekend adventure or Zoom meeting. This past year has been brutal, but it looks like we’re almost out. If you’re ready to inject some new life into your wardrobe, continue on below for our recommendations for styling casual outfits for men.


Work From Home Outfit One

A business casual dress code has a new meaning when you’re working from home. Because your commute is going from your bedroom to your living room, you can do away with laptop bags, outerwear and other stuff. If you’ve gotten into the rut of either rolling out of bed in sweats and then immediately going to work or changing from one pair of lounge pants into another pair of lounge pants to head to your home office, you’ve got to stop. What may feel comfortable for a while can actually affect your work performance, your attitude and well, everything. Take the time to put on “real clothes” before getting down to work.

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These days “real clothes” are heavily influenced by the athleisure trend. Now you can find clothing that combines elasticated waists and relaxed fabrics with enough tailoring that you won’t embarrass yourself if you have to hit the copy center or supermarket during the day.

When styling or creating your look of the day, don’t be afraid to mix up a trendy, casual pieces like a cardigan or oversized sweater with a long-sleeve t-shirt and athleisure-influenced bottoms. Outfits like that not only make you feel more pulled together but if you’ve got a video conference or two locked in later during the day, you won’t have to do a quick change to look presentable.

The new biz casual footwear style for WFM is as comfort first. When working at home, throw on soft suede slip ons, driving mocs, or sneakers or walking shoes.

Bonobos Off Duty Pant

Bonobos started out as a pants company, and early adopters raved about the brand’s fit and comfort. The Off Duty Pants are no exception. They are the perfect marriage between sleek, tailored chinos and comfortable, athleisure joggers. The elastic waist features an interior drawcord so you don’t need to bother with a clunky belt and they boast a super relaxed fit with a tapered leg that hits right at the ankle. Choose from a broad range of colors to feel comfortable without sacrificing style.

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Courtesy of Bonobos

Public Rec Go-To Long Sleeve Henley

Made with their proprietary tech fabric, this comfortable Henley has moisture-wicking abilities; it’s so breathable that you could wear it during a workout. Public Rec creates tech wear and athleisure-styled goods that wouldn’t look out of place at a weekend brunch. This shirt pairs neatly with the Bonobos pants and will become a staple of your casual wardrobe.

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Courtesy of Public Rec

Brigadoon Shawl Collar Merino Wool Cardigan

Working from home is all about combining style and comfort. Throw on a trending fluffy knit cardigan with joggers, jeans or whatever and your outfit instantly becomes smarter .

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Courtesy of Nordstrom

Raum Goods Slip-On

Looking for a well-made shoe that’s fit for business casual dressing? Try these slip-ons from sustainable brand Raum Goods. They’re fully lined in sheepskin and stitched with 100% cotton waxed thread. Raum Goods uses vegetable dyes, they have less impact on the environment. Raum Goods is based in Turkey, and a percentage of their workers are Syrian refugees. All leathers used are a by-product of the food industry, and they avoid using chemicals that can damage the earth. The company has partnered with 1% For the Planet and donate 1% of yearly sales to nonprofits.

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Courtesy of Raum

Work From Home Casual Outfit for Men Two

Repurpose climbing pants for a day at the desk. This work from home casual look for men also combines athletic styles with classic goods.

Vuori Ripstop Climber Pant

Outdoor outfitter Vuori has a range of pants that bridge athleticism, comfort and athleisurewear. Their ripstop climber pants can be worn for its intended use, and in the office as well. How and why? It’s the way they’re made. A quick glance at them, and you’d think they’re a pair of chinos. Made from organic cotton ripstop with a two-way stretch, they have an elasticated waistband, mesh pockets and a gusset for a wide range of motion. They have a 33-inch inseam, as they’re made to be worn cuffed.

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Courtesy of Vuori

J.Crew Brushed Wool Crewneck Sweater in Stripe

This striped wool sweater is a perfect cold-weather staple, so don’t hesitate or you may miss out. Between the classic style and multiple color options in solid and stripe, you’ll find yourself pairing it with tons of pants and wearing it again and again.

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Courtesy of J.Crew

Skechers Arch Fit Sneaker

They look like running shoes but feel like plump slippers. Skechers has podiatrist-certified arch support, EVA midsoles, removable comfort insoles and hugs your foot when you walk. Not only will they work with any athleisure-inspired pants, but they’ll also go great with jeans and chinos too. Are they a little dorky? Yes. But since you’re rocking these at home, you’ll appreciate the extra support.

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Courtesy of Skechers

Weekend Wear Option One

While it’s easy to fall into the sweatpants-and-sweatshirt combo for the weekend, add some more stylish casual outfits for Saturday and Sunday. Whether you’re running errands, going to a socially distanced party, or meeting friends for lunch, there’s no reason you can’t add some cool to your comfort.

By nature, weekend wear has a relaxed vibe. However, since everything feels like it’s much more relaxed these days, while it may seem counterintuitive, you want to add a bit more structure to what you wear off-duty. As mentioned earlier, what you wear or don’t wear does elicit a psychological response. Say, you’ve got a long task list, by throwing on a pair of Chelsea boots and a graphic t-shirt, everything becomes more of a fun adventure than a chore. Here are style tips for creating two weekend casual outfits that can take you from the big box store to an afternoon of fun.

Bellemere Silk Cashmere High Neck Short Sleeve Tee

Silk cashmere is a very fine type of cashmere that is perfect for fall and winter. It’s soft, smooth, and light and doesn’t pill or shrink like other materials often do.  Bellemere New York ethically sources its wool and works with fair trade firms. This sand-colored t-shirt is an even more relaxed version of the trendy knit polo. It can work well on its own when paired with jeans and a light jacket.

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Courtesy of Bellemere

Everyday California Challenger Hoodie Charcoal

Everyday California uses eco-friendly, sustainable materials in all of their goods. Their hoodie is made from eco-friendly fleece and the patch is made from vegan leather. Every purchase of this unisex hoodie goes to ocean preservation. Everyday California has partnered with 1% For the Planet and they donate 1% of yearly sales to Greenwave. The hoodie can be worn over Bellemere’s cashmere t-shirt (or any of your own shirts) and under a topcoat for additional warmth and style.

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Courtesy of Everyday California

Everlane Relaxed 4-Way Stretch Organic Jeans

Everlane delivers style and a transparent supply chain. They make their clothing to fit and last. Jeans are moving from slim fit to fuller legs. Their relaxed fit, organic cotton jeans mix up trends and ease of wear. Jeans are a weekend uniform, so why not pick a pair that’s fashion-forward and breathable? A high quality pair of jeans that’s perfectly tailored is key to building any casual wardrobe. Switch them up for work wear by pairing them with a button-down.

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Courtesy of Everlane

Puma Suede Classic Sneakers

Instantly identifiable, these Puma sneakers exude happiness and style. Plus, they pair easily with any casual look for men.

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Courtesy of Puma

Weekend Wear Option Two

Rock n’ roll never gets old, especially when you channel it into an off-duty outfit. Invest in casual pieces that can be styled multiple ways: like a graphic tee and button-up shirt. By building a collection of casual pieces that can be mixed and matched, you’ll end up getting more out of your clothes.

Coalatree Jacques Cousteau Long Sleeve Tee

Eco-friendly Coalatree salutes scientist and underwater explorer Jacques Cousteau with a black and white graphic printed organic cotton long-sleeve t-shirt.

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Courtesy of Coalatree

Amazon Goodthreads Standard Fit Long Sleeve Shirt

A button-down shirt and dark jeans could be considered a weekend wear uniform. With the exception of an event with a dress code, like a wedding or a fancy dress party, you can literally go anywhere in it and get admiring glances. Honestly, an Oxford shirt like this option from Goodthreads can save a look and give it a bit of polish. Switch the vibe by wearing it unbuttoned and over the above Jacques Cousteau t-shirt, it’s less formal and more relaxed.

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Courtesy of Amazon

Proper Cloth The Cortina Button Vest

Keep the easygoing feeling going by opting for a down vest instead of a jacket. Vaguely channeling apres-ski, Proper Cloth’s Cortina Button Vest is filled with premium down feathers whilst the front and back are made from soft birdseye flannel from VBC Wool. Details like the Italian horn buttons elevate the down vest from pedestrian to charming.

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Courtesy of Proper Cloth

Buck Mason Ford Standard Jean

Casually cool, heck you could wear these jeans as part of a WFH look. Buck Mason offers a durable denim pant with just the right amount of stretch to blend strength and flexibility. These jeans feature a classic silhouette that will instantly upgrade any outfit.

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Courtesy of Buck Mason

Thursday Boot Co. Legend Chelsea Boots

Chelsea boots have been a go-to boot style since the 60s. As much as it was a symbol of rebellion — the Beatles wore a type of Chelsea boot — they’re a wardrobe staple. They’re a bit like a blank slate, they have a clean silhouette and can be thrown into a trendy outfit, a classic outfit, etc. Thursday Boot’s Chelsea boots can be used for kicking back or kicking rocks. Made with a Goodyear welt construction, these matte black leather boots with their Poron antimicrobial shock-absorbing insoles are almost indestructible. Round out any casual look for men with this timeless boot.

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Courtesy of Thursday Boot Co.

Casual Date Outfit One

Let’s talk about dating. Nope, we’re not going to talk about all the various and sometimes strange dating rituals we have to deal with, we’re going to keep it simple and talk about what to wear on a date. Like everything else in our life, what we wear on dates now is much more casual. Regardless of how you used to approach dates, you can now go for a more easygoing style. That’s not to say you can’t add a touch of urbane sophistication to a look, you can totally do that, but comfort is also key. Why? Because so many dates are now held outdoors or at open-air cafes. So combine warmth and ease with our men’s casual attire guide below.

Madewell Slim Chino Pants: COOLMAX Edition

These slim-fitting pants from Madewell strike the right balance between carefree and tailored. Used as base for a date outfit or a WFH look, they’ve got the right silhouette that works with whatever else you match it with. The pants are based on jeans, so they’re oozing with comfort — the stretch fabric helps with that. They’re made to be fitted through the hips and thighs and end in a straight leg. They are also made with a moisture-wicking material that is temperature-regulating so you’ll be comfortable and dry during any season.

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Courtesy of Madewell

 Everlane The Heavyweight Overshirt

This piece of outerwear from Everlane is a cross between a jacket and an overshirt. It’s got the design of a shirt and the jacket’s sense of warmth and looks great on any body type. It’s a perfect alternative to trucker or denim jackets. Everlane’s is made from eight ounce heavy cotton twill that is durable and warm. Wear this under a jacket, over a shirt or sweater, or buttoned-up to steal the show. The possibilities are endless.

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Courtesy of Everlane

H&M Slim Fit Sweater

You can always count on H&M to give you style without depleting your wallet. This half-zip sweater is made of a fine-knit cotton and offers a tailored silhouette. Sporty and cool looking, it could be worn over a t-shirt or cotton turtleneck.

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Courtesy of H&M

Florsheim Crossover Lace to Toe Sneaker

Leather sneakers combine a touch of suave with ease, they quietly amp up whatever you’re wearing with you looking like you’re not trying too hard. If you’re planning a “walk and talk” date, these sneakers are made to cradle your feet. They’ve got a fully cushioned removable footbed and a molded EVA midsole.

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Courtesy of Florsheim

Casual Date Outfit Two

Mining the cottagecore trend with a dose of British style, this casual look for men works with whatever you’ve got on your agenda.

Dockers The Henry Wool-Blend Top Coat

Traditionally, camel hair coats were for formal affairs. Dockers remade the camel hair coat for the modern guy with its modern, boxy cut. This wool-blend jacket has buttoned cuffs and back vent details. It can also be tossed into a washing machine.

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Courtesy of Amazon

H&M Merino Wool Sweater

Merino wool is almost as soft as cashmere and just as durable. Done in a rich burgundy, this simply cut sweater lets you try it with all sorts of things. It’s got the right amount of panache to pump up an outfit without making it stuffy or uncomfortable. This might be the cold-weather version of the classy knit polo we all know and love.

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Courtesy of H&M

Flint and Tinder 365 Corduroy Pants

Corduroy by its very nature makes things just a bit more dapper looking. Could be the plushness or how it reflects the light, but they’re stylish without being stuffy. Flint and Tinder is an American company that prides itself on creating outstandingly well-made and comfortable essentials. Their corduroy jeans, they call them pants, but they look like five-pocket jeans, are made with 8 oz. blended fabric so they can be worn all year-round. These pre-shrunk pants are designed to have a roomy straight cut.

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Courtesy of Huckleberry

Florsheim Lodge Plain Toe Gore Boot

These Chelsea boots have an Ortholite footbed and a durable rubber sole. They’ve combined style and comfort in a chic boot that works well with just about any outfit. But more so than our previous Chelsea boots, we love this rich amber color, especially when paired with the pants and coat above.

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Courtesy of Florsheim

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