How to Dress Business Casual with Style – 10 Tips for Men

With the rise of more casual offices as well as the drastic increase in Work From Home, more and more people are dropping into the (somewhat dreaded) Business Casual level of workplace dress… even if that just means for the daily zoom call. But that doesn’t mean you have to look like every sitcom dad from the 1990s. Here are 10 ways to make Business Casual look, y’know, actually kinda good. Because enclothed cognition is real. Look good, do great. Now who microwaved fish again??

 

#1. Trim up your fit

Number one with a bullet. Even though fits have gotten much slimmer in the last decade (to a bad extreme in many cases)… the business casual workplace is still littered with oversized dress shirts and bulky khakis. Clothes should ride close to your frame, without constricting it. They should skim but not cling and not billow out. Look, with movement clothes will untuck, wrinkle, and bunch. AND THAT’S OKAY! Don’t shrink wrap yourself. But look for trim fit clothes that fit and feel great, and strongly consider developing a relationship with a tailor.

 

#2. Carry a briefcase that walks the line between casual and dressed up

• Gustin Made in the USA Deluxe Briefcase – $349
• Filson Made in the USA Original Brief in Cinder Gray – $199 ($300ish)
• Boarding Pass NYC Flight Brief – $215
• WP Standard Zip Top Briefcase – $319

You want a work bag that hits the middle ground. Somewhere between a casual, frumpy messenger bag, and an overly starchy hard sided attache. Look for something made from leather or canvas, with a bit of structure but not razor edged. You want to be taken seriously. You don’t want to look like the guy delivering lunch from an electric scooter. Even if you are the guy who often delivers lunch… maybe from an electric scooter. Because, c’mon. Everyone loves lunch.

 

#3. Tweak the “usual” khaki/blue/brown business casual color scheme

• Outfit 1: casual layers, nothing over $100
• Outfit 2: Working from Home, Smart Casual Enclothed Cognition
• Outfit 3: Warm Weather Smart Casual
• Outfit 4: Fall Business casual, blues and grays

Everyone wears khakis, blue and/or white button ups, and brown shoes. Mix that up! Instead of khaki chinos, go with green, deep brown, olive, or gray. Especially gray. WEAR MORE GRAY. Bounce contrast around, like instead of a lighter shirt, go with something more saturated under a lighter sweater or sportcoat. Or, go with a brightened up version of the standard office wear (try an aqua OCBD). Brighten up your footwear with lighter shades of cognac, or tan suede. You’re not wearing purple pants with black “going out” club shirts (don’t wear those… ever). Just take the norm, and tweak it a bit.

 

#4. Wear some unexpected footwear

• TBNY Positano Double Monk Strap Shoe – $236.90 (during the UPCOMING Nordy anniv. sale)
• Astorflex Evoflex – $130
• Banana Republic Nyle Suede Lace-Up Oxford – $100ish
• Allen Edmonds Liverpool Chelsea – $495
• Spier and Mackay Tobacco Brown Suede Wingtip – $248
• Cole Haan Grand Monk Straps – $90.99

It’s starting to look like a basic smooth leather “dress” blucher from Johnston & Murphy or Cole Haan is issued to every corporate worker bee when they get their key card. Try something different. Go for suede! Or monk straps! Or a contemporary sneaker-chukka hybrid! You’ve got options.

 

#5. Wear CLASSIC Brogues

• Allen Edmonds Strands – $395
• Mercanti Fiorentini Medallion Cap Toe Oxfords – $136
• Grant Stone LWB Crimson Chromexcel – $360
• Johnston & Murphy Conard Cap Toe Oxford – $149
• J. Crew Ludlow Semi-Brogues – $298 often on sale for less
• Aston Grey Wingtip Blucher – $89.99
• Banana Republic Hadley Italian Leather Wingtip – $100ish

So perhaps not unexpected, since it doesn’t get more classic than a brogue, but those perforated details and pinked (serrated) edges give this style of shoe all the eye-catching characteristics the blah-bluchers everyone else is wearing don’t have. If wearing something more modern/unexpected is too risky? Wear a brogue. It’s the original flashy (but not too flashy) footwear.

 

#6. Wear a sportcoat/blazer/unconstructed jacket

• Target tweed sportcoat (shown above, sold out)
• Spier and Mackay Washed Cotton Sportcoats – $149 ($198)
• Bonobos Unconstructed Italian Wool Sportcoats – $400
• Target Goodfellow & Co Knit Blazer – $50
• Suitsupply Havana Fit Blazer – $399
• Target Goodfellow & Co. Seersucker or Tech Cotton Blazer – $49.99

There are so many reasons to wear a sportcoat or modern blazer. They clean up your frame. They make you look slimmer and stronger. And they’ve got pockets to put stuff in. Keep it soft in terms of construction and breathable in terms of fabric (wool or lightweight cotton) and you can wear these with everything from a dress shirt to a casual button down to over a t-shirt. Yes really.

 

#7. Throw a little retro in there

• Orient 2nd Gen. Bambino Ver. 2 Automatic Watch – $170
• Banana Republic Glenn Sunglasses – $78
• TheTieBar Tipped Sweater Polos – $45
• Kent Wang Keyhole Sunglasses – $55
• Target Goodfellow & Co Striped Sweater Polos – $19.99

A watch with classic design elements. A trim polo worn with some sharp wool slacks. Clubmaster style sunglasses or frames if you wear a prescription. Items with classic menswear design elements are somehow looking great right now, along side more modern bits and bobs. Throw a little, uh, throwback, into your look.

 

#8. Own the details (accessories, pocket squares, watches, belts)

• TheTieBar Pocket Squares – $10+
• Allen Edmonds Merino Blend Patterned Socks – $9.97 ($19.50)
• Warby Parker Eyewear – $95+

Last things on, first things noticed. Pocket squares, socks, your watch… it’s often the little stuff that can help you stand out. Hopefully in a good way.

 

#9. Get into cardigans

• LL Bean Cable-knit Shawl-collar Cardigan – $109 ($149)
• Amazon Goodthreads Merino Cardigan – $40
• J. Crew Factory textured shawl collar cardigan (sold out)
• Uniqlo Airism UV protection cardigan in Navy – $9.90 FINAL ($29.90)
• J. Crew Cotton Cable-Knit Shawl Cardigan – $26.32 FINAL ($138) sold out, naturally

Get over the grandpa/Mr. Rogers stigma. They can either be warm and cozy (think cable knit, shawl collar styles), or they can be sharp and contemporary (trim fitting merino cardigans). Either way, they clean up your lines since your shirt isn’t wrinkling at your sides, and they’re a defacto “sportcoat” style-layer, without the extra formality jackets bring with them.

 

#10. Casual Fridays = Sneaker Fridays!

• Made in Italy Good Man Brand Pebble Leather Sneaker – $129.90 ($198) (during the UPCOMING Nordy anniv. sale)
• Nike Killshot – $90
• adidas Stan Smith Upgraded Leather – $90
• Nike Zoom Freak 1 – $120
• Nisolo Men’s Leather Low Top Sneaker – $150
• Huckberry Exclusive USA Made Resoleable Victory Sportswear Runners – $220 currently sold out
• adidas Ultra Boost 20 – $180
• Nike Air Tailwind 79 – $90

Casual Fridays are only going to get more casual now that people are barely wearing pants… or deodorant. Plus, we’re living in a new, golden age of sneakers. So lobby your Boss for sneaker Fridays. A day to show off your classic court kicks, your just released basketball sneakers, or for the big-time sneakerheads, your weird designer stuff.

Any other tips for WFH / Business casual looks that are still stylish? Send those tips into joe@dappered.com. Items shown at the very top of the post are: Brooks Brothers Wool/Cotton Knit Sportcoat (sold out), Mizzen & Main Check Button Down – $53.50 ($125), Lululemon ABC Pant – $128, Smartwool Socks – sold out in navy, Banana Republic Suede Double Monks (sold out).