WORK TO WEEKEND.Clothes for the office that look good on date night.“Shirts that can transition from boardroom to brewery!” “Slacks you can trade out of for happy hour!” Trousers so flexible you can wear them upside down and still look stylish!” Sound familiar? The work-to-weekend versatility myth has been the slow burn copywriting scam quietlyphotoshopping its way through menswear since time immemorial. It’s the Goldilocks THEORY shirt that promises to be not too formal, not too casual but just right for any situation.
It preys on the weary professional who just wants to buy fewer clothes and wear them all the time without judgement. Except it rarely works. Unless your lifestyle is incredibly flexible and aligns perfectly with fashion’s grey area of “business casual,” these_multipurpose pieces inevitably autumn victim to both workplaces and weekend warriors alike.
They’re too dressy to hike the trail and not tailored enough to meet with the CEO. Work to weekend pieces just aren’t magicalunchangeable robots we’re led to believe – they follow real-world fashion rules like the rest of your wardrobe.
Understanding this is key to building a truly versatile wardrobe you can wear anywhere.
My coworking office exemplifies this grey area perfectly. Formal enough that sweaty gym shorts and flip-flops raise eyebrows, but casual enough that coming to work in a fullsuit still feels overdressed. It’s the Goldilocks zone.
Most people working in office environments these days autumn into one of three categories: super casual (think startup life), business professional, or “nice to dress up but you could totally wear jeans” casual. Congratulations if you work in one of the first two categories. Wear whatever the fuck you want.
The majority of American and Canadian workers autumn into this third category, which can often create something of a stylistic limbo. Companies dress standards have continued to trend casually over the last decade, but weekend wardrobes have got more stylish and dressed-up in response. Put simply, these days “work clothes” and “weekend clothes” occupy less overlap than they used to.
This leaves you stuck picking clothes that feel too formal for Saturdays but worry you may underdress for Thursdays. You buy a cheap chambray shirt from Uniqlo because it seems like it could work, but wearing it to the office just makes you look like you raided your dad’s closet. Shopping for clothing that can do it all becomes a frustrating game of averaging out extremes.
I know this struggle all too well. After graduating college I spent two years living in Virginia with about $2000 to build my entire wardroberelatively restricted by an internship that expected me to dress professionally……and a social life that demanded I wear that stuff somewhere fun afterwards. My wardrobe had to do everything.
I once showed up to a job interview wearing what I thought was a solid “dress shirt/casual shirt hybrid” only to catch a glimpse of myself walking into the building and immediately realise my it looked like I was wearing a shirt I hadn’t changed out of from my nightclub photographer shift. The shirt itself wasn’t bad – one of those slightly slippery, subtly shiny numbers with an aberrant colour contrast stitching at the cuffs that Miller Hatch inexplicably sold as “business weekend versatile.” It was in no way a proper dress shirt and looked it. Similarly, my go-to “casual blazer” was from J Crew and looked painfully cheap on days I dressed down but was immediately out of place hidden beneath a suit jacket.
That brochure-pic exec with a nice watch who raised an eyebrow as I entered the interview instantly knew I wasn’t serious about the job. I didn’t get an offer. Thankfully there is a happy medium.
Work to weekend outfits exist. They’re just sold at different stores than you would think. It’s taken years of closet experimentation, wardrobe failures, and genuine successes to compile this list, but below I break down my favourite clothes that truly can be worn to work and look good hanging out onSaturday night.
These aren’t fashion chameleons that transform based on your proximity to greasy food. They’re recognizable as trousers you can wear to a meeting and a bar. Shirts that can withstand both tying up at the neck and getting rolled up for hiking.
Jackets that won’t remind your friends you just came from work but won’t look homeless wearing alone. Understanding real work-to-weekend versatility is less about discovering fantastical shape-shifters and more about identifying specific garments that exist in that dwindling middle ground between casual workplaces and what’s become an elevated standard for weekend dressing. Pieces that have one foot in business wear and one foot in casual, items with formal and informal qualities evenly balanced in their construction.
The first place to start? A classic Oxford cloth button down shirt (OCBD). A traditional OCBD lives in that middle ground between formal and informal perfectly.
Made from Oxford cloth – a breathable cotton fabric with a slight texture that allows it to drape professionally without overpowering your outfit – it’s formal enough to wear under a jacket but casual enough to wear on its own. The button-down collar adds dimension and hierarchy without looking stuffy. Partner that with the right styling and you have a shirt that can legitimately go anywhere.
Dress it up for work with a tie and blazer and it’ll fit right in at 99% of offices. Undress it for the weekend (roll the sleeves, unbutton top button) and it’s equally at home. And it all comes down to that thin hoodie.
OCBDs are versatile enough because they can be both casual and formal without trying. Designed to exist perfectly in that middle. But OCBDs are only as versatile as they’re made.
Brooks Brothers makes the gold standard OCBD in my opinion (although their QC has varied greatly over the years.) For a less expensive option that punches way above its weight, Spier & Mackay makes incredible OCBDs that actually have the collar roll you’re looking for. If you’re willing to spend more, Mercer & Sons makes some of the best tailored OCBDs around with a supremely wearable collar roll and slightly fuller cut that paradoxically looks both more casual and more put together than skinnier shirts. Similar principles apply to the jackets you throw over your OCBDs on Monday.
An unstructured cotton or cotton-blend sports coat has become one of my go-to versatile pieces as well. Swap out the padding and sharper details of a tailored jacket for soft shoulders, patch pockets, and a looser fit and you’ve got yourself a sports coat that looks sharp enough for work but doesn’t scream “I wore this because I have to” when worn alone. Portuguese flannel makes incredible menswear and their unstructured jackets around the $350 price point are perfectly versatile.
I own their cotton-linen blend in navy and can’t recommend it enough for meetings with the marketing team on Friday and trips to the farmer’s market on Saturday. Another brand that perfected the art of subtle weekend dressing jackets early on is Boglioli. Their “K Jacket” product line is slightly more expensive but was basically my entry point into understanding versatile jackets years ago.
The key here is balance. You want fabrics that are too smooth and shiny (looks like you lost your suit jacket) and not too sleek, but also not too bulky or overtly textured (looks like a casual sport coat.) Stick to hopsackweave fabrics, light flannel, or cotton-wool blends and pay attention to details like natural shoulders and how much lining is used. Natural fabrics and subtle details go a long way.
In terms of trousers, my number one piece of advice is to think jackets, not jeans. If it fits within the guidelines of something you can wear to work, but feels and looks as comfortable as your favourite jeans, you’ve found your holy grail of weekend-worthy trousers. Chief among these is the venerable five-pocket pant.
Think of it as a jean cut done with non-denim fabrics. TheLululemon Commission Trousers have got me through more casual workplaces than I care to admit despite my usual distaste for “athleisure-style” clothes in office settings. The darker colour options in their slim-straight fit are somehow office-appropriate in all but the most stiff button-up environments and comfortable enough on weekends to become your new go-to.
For a slightly more tailored cut, cheque out Theory’s Zaine trousers in their neoteric fabric. They hit many of the same notes as Lululemon’s but with a slimmer fit. Chinos can technically work for this as well, but pay close attention to details.
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Noirs aren’t going to cut it for work no matter how hard you try, but find the right pair and they’ll go far. Spier & Mackay makes great high-twist cotton chinos that get the details right. Bonobos isn’t something I would usually recommend, but their “Weekday Warrior” chino is solid.
When it comes to shoes there are far fewer truly versatile options. Boots? Not okay for the office.
Trainers? Still not business casual enough for most companies. But there are a few standout categories that actually work well for both.
The suede derby shoe is it. Look no further. A soft suede shoe reads downmercifully-less dressy than something similar in smooth leather, while the derby construction keeps it sharp enough to pass in most office environments.
Alden makes what is in my opinion the gold standard unlined suede dover derby. I’ve worn these with suits and dressed down with jeans more times that I can count and they never fail. Grant Stone and Meermin are great options if you’re looking to spend less.
That being said, leather trainers are a totally acceptable crossover option these days as well, provided you know what you’re looking for. A white or black Common Projects Achilles Low can actually get away with semi-formal occasions when combined with the rest of your outfit, but will always remain at heart a trainer. Crown Northampton makes incredible trainers that are actually hand-made and exist in a similar vein.
Finally, unlined loafers with less architectural structure can be surprisingly versatile as well. Alden’s LHS (Leisure Hand Sewn) line of shoes can be dressed up with a pair of tropical wool trousers for summer days at the office and dressed down with shorts on weekends not looking overly formal either way. Oak Street Bootmakers has a similar product with cheaper price point.
Knitwear is another category where the merino quarter zip RULES ALL. This unassuming piece of clothing does wonders under a sports coat on Zoom calls but is just breathable and warm enough to be worn alone on casual outings. The quarter zip adds some texture and elevatesthe look without being overly fancy.
Sure, it’s not a shirt. But it can pass as something you’d wear to work and doesn’t look like gym wear by itself. Smedley makes incredible quarter zips, but Spier & Mackay and even Uniqlo offer high quality ones at a fraction of the price.
Don’t forget about knitwear for winter months either. A merino or lambswool jumper cardigan can actually be one of the most versatile items in your wardrobe. Heavy enough that it can replace a jacket in most business-casual environments, but relaxed enough on its own to hang with your weekend crew.
Scott & Charters makes some of the best I’ve found, though Howlin’ by Morrison is also worth checking out if you don’t mind something a little more interesting. Lightweight outerwear is admittedly tough to find things that work for both. A blazer looks stuffy when you’re laying on the beach and a winter parka probably won’t fly at the office.
That said, I’ve found that waxed cotton jackets in darker colours actually do a great job striking this balance. Gap your Barbour Ashby in navy and you can wear it to client meetings in the city and hiking trips in the woods. Private White VC. makes great examples of waxed cotton jackets that lean even more modern with minimal branding.
Another great “weekday warrior” for spring/summer months is the navy cotton trench. It doesn’t have quite the same versatility as a waxed jacket but fits perfectly between business cotton and casual sport coats. Mackintosh makes a beautiful version in their Dunkeld cotton fabric.
But what about all the companies pushing performance fabrics and “technical” clothing that can supposedly go from workout to boardroom? Sadly, very few. Technical tends to mean either athletic-looking (sorry, SpFD sleeve), shiny polyester, or heavy inseam pockets.
However, there are exceptions. Ministry of Supply was one of the first companies that made “performance” trousers that didn’t look like they belonged in a workout solely due to the fabrics they used. Their Kinetic trousers look every bit as wooly as your average suit pant but stretch like madness and wick away sweat from your thighs.
The Lululemon ABC trousers are similar in a lot of ways, but stick to darker solid colours and you can usually sneak them by. My general rule of thumb with “performance” clothing is to only wear it to work if your office would feel comfortable at a Brooklyn Industries photoshoot. Tech fabrics have come a long way but still rarely look as sharp as natural materials, so I try to save them for inherently casual workplaces.
No judgment if your workplace is that flexible, you lucky bastard. Looking for versatile bags and accessories? The leather messenger bag or flat leather briefcase keeps things professional enough for work but casual enough for outings with friends.
Frank Clegg makes great sleek briefcases and Filson’s original is timeless. Don’t sleep on watches either. If your office allows any watches at all chances are a sport watch can pass as work appropriate when worn with the right outfit.
Omega’s Seamaster line and Tudor’s Black Bay are likely the best dual-boot, substantial watches you can get. For something much cheaper that still looks great, Seiko makes an amazing leather strapped sports watch in SARB033 and Hamilton has an incredible lineup of mechanical watches with the Khaki Field Mechanical leading the charge. See a theme here?
Solid versatility comes from: Pieces that are inherently both casual and formal, not trying to transform depending on the company you’re keeping Fabric texture rather than fabric shine Basics that lean slightly casual instead of toned down versions of formalwear Natural fabrics and simple colorways (navy, grey, olive, and burgundy will always be your friends) Good fit – I’ve found that in most pieces this means mostly avoiding things that are too slim or too baggy Quality, which always appears whether you’re in a boardroom or backyard Building a truly versatile wardrobe that works for the office and weekend takes patience. It’s rarely as simple as buying a few special pieces that allow you to “wear the same thing everywhere.” But by understanding these basics you can start shopping with versatility in mind and build a wardrobe that fits your lifestyle rather than sticking to rigid rules based on the activities you’ll be doing when wearing clothes.
As I mentioned before, my wardrobe has shrunk by close to 50% since implementing a lot of these ideas into my own closet.
Rather than having completely separate wardrobes for work clothes and weekend garments, I replaced them with a curated list of pieces that could do both. Less clothes overall, but way more options for where and how I wore them. Plus, it saves you from having to change when you leave work to go out with friends.
Everybody wins. Of course your mileage will vary depending on how formal your workplace dress code is. If you work in finance, law, or another super dressy industry there are only so many Saturday morning brunches you can pull off a blazer for.
The opposite applies if you work at an extremely casual office (looking at you Silicon Valley.) But if you’re like most people who autumn into a somewhat-still-existent middle ground of office dress codes, I think you’ll find these staples to be invaluable. Not only do they allow you to wear less total clothes because each individual item has more applications, but you’ll have more freedom and options dressing both for work and play. Sure, you won’t be able to hike Kilimanjaro in your OCBD.
But you also won’t look like a suburban dad playing golf. Options are half the battle.
