6 Ways To Wear Your Boring Blue Work Shirt All Week

The blue dress shirt, it’s hardly the most exciting of propositions. And yet, it is by far one of the most dependable items hanging in the wardrobe today, capable of getting men through mind-numbing Monday meetings, late nights behind the keyboard and more head-bludgeoning Friday hangovers than most maybe care to admit.

So perhaps it’s time to stop overlooking this admittedly understated piece of kit, and start treating it for what it truly is – a shield against the drudgeries of the 9-5 or, if you prefer, a grown-up comfort blanket with the power to do overtime on the weekend.

But how do you keep this humble piece of menswear looking fresh, you ask? By giving it a swift upgrade and a little styling finesse so that you can wear it with everything, everywhere. Here’s how.

Blue Dress Shirt Checklist


The most versatile blue dress shirt is one that fits you, unsurprisingly. Which means next time you’re re-stocking your rotation, it’s wise to take a second to consider your build and what cut suits it best.

“If you are fairly slim, then a few darts in the back will give you a leaner look,” whereas those with a larger frame “will probably be more comfortable with a straighter cut,” explains Savile Row shirtmaker Stephen Lachter, who has created bespoke versions of this staple for the likes of Frank Sinatra, Cary Grant and members of the royal family.


To get the most out of your dress shirt all-week round, it’s best to indulge in some blue-sky thinking. Quite literally.

“A mid- or sky blue dress shirt is perhaps the most versatile, and will go perfectly well with navy, grey, beige or brown,” says Lachter. The reason for this is that while darker hues are good for casual outfits (in the case of the chambray shirt), they can be tricky for more formal occasions.


Like your sunglasses and your haircut, the collar you choose should suit your face shape. A spread collar can have a widening effect, adding balance to those with long, narrow faces, not great for those with softer, rounded features who should instead choose a more narrow point.

To strike the sartorial middle ground, Lachter suggests a semi-spread or forward point collar, “[this] can be worn with or without a tie and is much more versatile than a spread collar,” he says.


Yes, you might have been gifted a sterling set of cufflinks for Christmas, but that doesn’t mean you need to crack them out at every opportunity, particularly if you want a work look that also puts in the hours at the weekend.

“French cuffs are quite formal and therefore more restrictive if you plan to wear your shirt away from the office,” says Lachter. “A button cuff is the most versatile option.”


The best type of fabric for a work shirt? The answer’s wrapped up in the proverbial piece of string.

“The hardest wearing is an Oxford cloth, but this is rather heavy and perhaps better suited for casual wear,” says Lachter. Instead, the shirtmaker suggests opting for a plain weave cotton (a two-fold 120s poplin, to be precise) for a fresh, clean look that has the added benefit of being pretty wrinkle-resistant.

6 Ways To Wear A Boring Blue Work Shirt

Fully Suited

A navy suit worn over a sky blue dress shirt is one of the safest options in the menswear playbook, but it can also feel a little meh if repeated too often. To spice up your office attire, ditch standard shiny materials in favour of something with texture or pattern.

Grey flannel is endlessly more interesting, as is – for those who dare – a retro-tinged brown mottled wool, especially when worn with a striped tie and heavy-soled shoes or boots. Or in the warmer months, try a tropical-weight wool in dark green or grey, experimenting with subtle checks and stripes.


A blazer, jeans and blue dress shirt combination is the definition of smart-casual, but it’s a look that many guys are wary of for fear of looking like a middle-aged dad at a Top Gear convention.

To avoid such comparisons, start by choosing the right jacket. This usually means something unlined, unstructured and preferably single-breasted. As a rule of thumb, stick to dark indigo or black jeans in a tapered or slim fit, which you can wear with clean white sneakers. Keep your shirt tucked in, leave the tie at home, and consider a light-coloured crew neck to help break things up.


In recent years, the preppy look has shaken off its hoity-toity connotations and returned to the wardrobes of those looking for solid everyday outfits that make a lasting impression.

A navy blazer worn with khaki chinos is perhaps the quintessential Ivy League pairing, something which can be thrown on with a blue dress shirt, a knitted tie and a pair of penny loafers. If a jacket isn’t essential, swap the blazer for shawl collar cardigan or cable knit jumper, and the loafers for a pair of retro running shoes to add a more modern edge.

Scandi Cool

Like most guys, we often ask ourselves why we haven’t just upped sticks and moved to Scandinavia already, what with the shorter working hours, minimalist everything and generally better quality of life.

It’s something you can try to manifest by ditching the laced-up look in favour of a bolder, Nordic-inspired silhouette. Start by tucking your blue dress shirt into a pair of slightly cropped, pleated trousers, worn with a boxy chore jacket or roomy sweatshirt. Finish the whole thing off with a pair of suede desert boots or – if you can get away with it – clean white tennis shoes.


Though wearing separates is all about creating a distinct contrast between your jacket and trousers, it’s also important to keep a connection between the top and bottom half. Sounds simple, right?

An easy way to achieve this is to wear navy trousers with a blue dress shirt, as the consistency in colour between the two will give you (almost) free reign with it comes to choosing a jacket. Remember to aim for a noticeable difference in colour and tone – your mismatch should feel purposeful, not accidental, so stay away from dark blues or blacks and instead go for a grey or burgundy in a similar weight and fit to your trousers.


Though it might seem strange to bring a reminder of the office with you on holiday, packing a blue dress shirt is a much better idea than splashing out on that pink linen number you’ll seldom wear on home shores.

This is where having the right fit truly works in your favour – if your shirt is of the billowing, shapeless variety, you’ll look more David Brent at Bognor Regis than Tom Ripley in Mongibello. Keep it slim and wear it open over a plain white T-shirt or vest with the sleeves rolled up, paired with navy chino shorts, sandals and – if you’re lucky – a glorious tan.