Not every shirt is made equally. While we’ve come to know the collared classic as a throw-on-and-go solution to looking refined at work, or adding a sophisticated edge to a soirée ensemble – the devil really is in the detail. Knowing those details is what separates the boys from the gentlemen. From buttondown to overshirt, slim cut to straight, patterned to poplin, every one of them is made to see you through a specific reason, season, occasion or atmosphere. The key to being the sharpest dressed guy in the room is knowing the difference.

 

THE OVERSHIRT

Some things in our wardrobes just work harder than others. The overshirt (sometimes called the shacket) is probably the most versatile shirt you’ll ever own. Heavier than a shirt, but lighter than a jacket, it’s the perfect piece to layer underneath your outerwear in winter and wear unbuttoned, over a light tee on cooler summer days.

 

Textiles to try: Heavyweight cotton or lightweight denim.

Fit notes: Keep it boxy and oversized for a slimming effect, making you look taller.

Stylist’s tip: While it may be smarter than your bomber jacket, this guy is still considered a casual shirt and is best suited to streetwear-inspired looks.

 

THE DENIM SHIRT

This trusty wardrobe staple seems to make an appearance on the runway every few seasons, each time updating the way to wear it. Most recently we saw a Western take on the denim shirt, but you don’t have the horses in the back to make it work. It’s versatility has made it a signifier of everything from The Yeehaw Agenda to laidback, I-just-threw-this-on cool.

 

Textiles to try: Well… denim.

Fit notes: Straight cuts are perfect for relaxed looks and layering over tees, while slim-fitted cuts are better suited to tucking into trousers for Western-inspired looks.

Stylist’s tip: Recommended for casual settings, the most effortless combination with a denim shirt is simply thrown on over a tee (try striped for some interest), with a clean-cut chino. For the more adventurous you may want to try denim-on-denim. If that sounds like you, you will want to make sure that your denims match identically in colour, or contrast quite dramatically, otherwise risk looking lazy. Rolling up your sleeves may help break the tonality of the look and make it feel less overworked.

 

THE LIGHTWEIGHT PRINTED SHIRT

It doesn’t get any more functional than this. A light, printed shirt is the perfect companion to your suit for dressier summer events when the rigidity of a conventional shirt just doesn’t make sense. Nothing beats it’s soft touch on your skin when it catches the breeze on a sweltering sunny day or balmy evening. While it may be tempting to whip out every time you need to wear a suit it must be noted that no one will take you seriously wearing this in the boardroom or at your own wedding. Don’t be a clown.

 

Textiles to try: Viscose, polyester, linen or a very light cotton.

Fit notes: Regular or loose fit. Any obvious tailoring will spoil the naturally airy, relaxed look of the shirt.

Stylist’s tip: Easily worn under a suit, or over a tee with sleeves rolled up and paired with shorts. Buttons become a tricky subject. While rising temperatures may push you to gradually become undone over the course of the day, the furthest you should respectfully unbutton is the third button from the top. Yes, even you with the chiselled six pack, sir.

 

THE BUTTONDOWN SHIRT

For some reason this is the most perplexing shirt for man to wrap his head around. Where it’s appropriate to wear has been a hotly debated topic for decades, while some are wondering when it’s alright to unbutton the collar. To the latter the answer is never. The collar-tip buttons should typically always stay fastened, or risk this casual shirt looking sloppy. On the question of where to wear it – the buttondown shirt was created for the polo field, as a leisure shirt, making it wildly inappropriate for any formal occasions, even if it’s paired with a tie. It is best worn anywhere that calls for a smart-casual dress code.

 

Textiles to try: A trademark fabric for the buttondown is Oxford weave. This weave uses two different colours of unbrushed cotton, woven together to form a textured, soft fabric. Cotton poplin may be less textured but is also suitable.

Fit notes: Even though the shirt has a relaxed tone, the ideal fit is regular or slim to maintain structure.

Stylist’s tip: All your pieces should speak the same casual language – unstructured jackets or linen blazers, chinos or jeans pair best with the buttondown. Sure, you can throw on a tie but stay away from silky finishes that are better suited to formal occasions and opt for a woven tie.

 

THE SMART SHIRT

It’s near impossible to begin to talk about every variation of the smart shirt, but the fundamental rules are quite simple – It’s all in the collar. The height and spread of your collar should make sense for your environment and should complement the shape of your face.

Round faces and bigger heads are complemented by tall collars that match the large proportions of the face, while a short collar would quickly make you into a bobblehead. A narrow collar spread (meaning collar points are close together) helps to create balance by creating the illusion of length.

For narrow, long or square shaped faces – shorter collars match the proportions of the head, and wide collar spreads can round out the face.

 

Textiles to try: 100% cotton is the traditional standard, but modern synthetics have been developed to include moisture wicking qualities and regulate body temperature.

Fit notes: An up-to-date look calls for a slim fit that skims the figure, yet doesn’t hug it, but not so loose that it bunches up under a jacket.

Stylist’s tip: This is not the shirt to pair with your jeans. Dress it down with a pair of chinos or for formal occasions opt for trousers. A little secret about underwear – they don’t just hold you in, they’re also the answer to keeping your shirt neatly tucked. Try it once, thank me later.

 

THE MANDARIN COLLAR SHIRT

While the suit becomes more relaxed, so does the stuff that we wear with it. 21st Century rules mean it’s okay going topless under your suit, but if you’re not keen on ghosting your shirt you could find a little bit of irreverence in ditching the collar. The nifty shirt with Chinese origins works just as well with a pair of jeans as it does under tailoring. Buttoned all the way up it reads clean and minimalist, while buttons undone feels effortless and relaxed.

 

Textiles to try: Formal iterations in cotton poplin or 100% cotton, or casual versions in Oxford weave, denim or linen.

Fit notes: Pretty much any fit suits the flattering cut.

Stylist’s tip: The rules aren’t hard and fast – the modernity of the shirt lends itself to any occasion or look. One tip: don’t wear a tie!

All shirts available from in-store & online exclusively at Markham.

Akim Jardine – MKM guest fashion editor