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How To Wear Plaid Without Looking Like A Dodgy Uncle

Incorporate flannel shirts in and out of the office without looking like your teenage self.

At the back of every man’s wardrobe sits a flannel shirt, in all its musty, moth-holed glory. It’s been worn to concerts, band rehearsals, and enough pub crawls that you begin to think it’ll outlive your grandchildren. If you haven’t owned one, most of your mates have (and probably wonder what you wore as a teenager). Whether you found it on a rack at Vinnies or a glossy department store, the flannel shirt seems universal at a time where fashion is determined on a weekly basis.

In common Aussie parlance, flannel shirts usually refer to coarsely textured shirts with an oversized multi-colour checked pattern (we don’t call ‘em plaid here). However, the strictest definition of flannel refers to any fabric (usually wool or cotton) that’s undergone a washing and napping process to achieve a fuzzy, raised texture.

Flannel is often brushed to smoothen the raised fibres. But it’s often left as is. The final result is a soft and warm fabric that has utility for anything from bedding, kilts, and blankets to Pearl Jam’s touring wardrobe.

Even if you’re not kilting it up, it’s true that every guy has room for a solid flannel. This style of shirting has no limits – whether you’re a barista trying to look like a lumberjack or just a guy who needs a shirt for Saturday night. If you need to add a pop of colour or pattern to your sartorial game, then you could do a whole lot worse (lookin at you, Tapout).

Here, we’ll tackle how to incorporate the flannel shirt in and out of the office, and offer some key pointers on how to avoid both ending up on shit style Instagram feeds and looking like your teenage years aren’t quite behind you.

Plaid Shirts With Jeans

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The dependable flanno + jeans look needs no real introduction – you’ve done it, I’ve done it, you’ve probably given your old man pointers on it. A flannel shirt and jeans combo is inoffensive and practical, suitable for anything from a boozy lurch across town, to a post-class procrastination session at a nearby café. It has more visual interest than a plain shirt and trouser look, but it just as versatile for most situations. For the flannel, stick to a slim(ish) cut. Make sure the cloth weight is harmonious with everything else in consideration. Avoid wearing a lightweight, crisp shirt with 16oz selvedge denim, or a bulky overshirt with skinny jeans. For a smarter interpretation for the casual flannel wearer, wear slim (but not too slim) grey jeans or wool trousers, chocolate brown Chelsea boots, a white tee, and a multi-colour flannel to finish it off.  This is perfectly acceptable after-hours-drinks attire, without making you look like you still worship Kurt Cobain.

Short Sleeve Plaid Shirts

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Sure, flannels are mostly associated with winter wear – they’re often heavier than your run-of-the-mill cotton oxfords and the fuzzy texture doesn’t seem suited to other seasons. But many retailers offer light or mid-weight flannels that have year-round versatility. For a casual afternoon, pair a lightweight flannel, navy chino shorts, and your nicer white sneakers (that you’re usually too scared to wear). Roll up the sleeves and undo the top two buttons for a definite weekend-off look. For summer, light colours work best. Pale checks with a cream, light brown, or blue tone are in tune with the season.  Try to avoid combining patterns initially; if your shirt has big checks then keep the shorts to a single colour (party up top, business everywhere else).

Plaid Shirts With A Winter Coat

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If your corporate overlords have said their last goodbyes to the jacket and tie, you might be left in the abyss wondering how to approach the company hustle without the comfortable fall-back of the traditional two-piece suit. Fortunately, the flannel shirt can step into the breach. This requires is a mid-weight flannel in seasonally appropriate colours, with a stiff collar (soft collars are a casual thing and not likely to impress in the office). Combine this with chinos that are on the smarter end of the spectrum – a tapered leg, raised front, in a charcoal, navy, or deep brown. In this instance, experiment with different patterns. Smaller checks, such as a gingham, tend to be less of a heat-seeker in the office. They’re also easier to incorporate with a tie, should you find yourself not quite ready to dispose of the silk noose. If your flannel shirt is a little roomy, trundle down to your alterations specialist to get darts inserted in the back of the shirt. This will let you avoid the ghastly muffin top look. Slightly cuff your chinos so they don’t crumple at the hem, and wear a belt that matches your shoes – ideally oxfords, but boots are a definite winter alternative. This is perfect for the casual Friday, or even the whole week if the suited-and-booted dress code has finally gone in the bin.

Plaid Shirts With A Suit

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You might be wondering how a flannel shirt could possibly look respectable in front of the people who determine your salary and have the power to cancel your leave at a moment’s notice. Corporate environments, however, have been generally more accommodating of unusual ways to wear a suit, so if you wanted an opportunity to give your white shirt a siesta, now’s the time.

There’s a few straightforward ways to start. A pale blue prince of wales check underneath a navy tie and charcoal suit is business savvy and dashing as hell. For a wintry look, a green gingham check shirt with your staple navy suit is a solid route to adding an unusual, but business-appropriate colour choice outside the ordinary parameters of grey and blue.  If you are tie-free, an oversized flannel check can also replace the role of a tie, by adding colour and pattern to the open gap between the jacket gorge and buttons.

Obviously, pick your battles. If the guy you need to impress for a promotion is a buttoned-up white shirt warrior, then pick a crisp, lightweight shirt with a discreet check over something bold and glorious. Quick tip – if you’re wearing a thick flannel shirt, try to pair it with a suit that’s of a similar texture and density. Otherwise you might be tossing the sartorial balance out the window. A heavy weave flannel shirt will rubbish a super150’s merino wool suit, and vice versa. Play it safe, test a few combinations and see what cops suspicious second glances from the HR people on Monday morning (and leave an ironed white shirt at the back of your locker just in case).

Plaid Coats

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Layers, right? Flannels are generally heavy, so they’re a spot-on choice for chilly day layering – a tee, puffer vest, overcoat, mackintosh, overshirt, you get the picture. Flannels are made in varying weights, so you have endless choice for how to approach your layering. Colourful check flannels are also useful in breaking up the tonal monotony of a monochrome layered look, so you’re not short on options. Whether it’s just a thin flannel under a parka, or a bulky flannel overshirt worn over a thin hoodie and tee for a streetwear-sportswear combo. A white tee, oversized green and yellow flannel, and bomber jacket is another off-duty winner, offering the right mix of ruggedness and streetwear. Keep the seasons in mind when you try this. For autumn, you might need nothing more than a flannel and puffer vest, while winter might warrant a four-layer plan of attack along the lines of a t-shirt, flannel, anorak jacket, and beanie to close off the look.

Flannel / Plaid Style Wrap Up

Don’t do up the top button, ese. It looks Brooklyn hipster or gang member and you’re hopefully not either, so make sure that button doesn’t touch the buttonhole until you’re carefully folding it back into your wardrobe (or cracking on with a half Windsor).

Do get a variety of options – various colours, various patterns, and various shapes (oversized, slim, and so on). Flannel shirts and their ordinary checked siblings have tremendous value in your wardrobe and can add colour and interest to even the most dull, last minute outfit you could think of. Buy a wide selection if you have the means.

Don’t wear it around your waist (for now). Even if you’re having trouble letting the 90’s go, it’s a tricky thing to pull off and few guys have enough sprezzatura to carry the look home.

Do pick seasonally appropriate colour choices. Grey and dark green are your winter staples. Lighter brown for autumn, and then cream and white patterns for summer. These choices will reflect attention to detail, and be harmonious with your surroundings.

Don’t combine casual flannels with tailoring, and tailored shirts with your casual ensemble. It looks wrong. A crisp prince of wales check shirt looks mustard with a suit. You’ll look like your dad if you tuck it into your bootcut 140z Japanese denims.

Do pick suitable cloth weights for your environment. Avoid Antarctica-friendly thick flannels in the office. Same story for lightweight blends if you’re about to do a risky winter run to the bottle-o. Check the weather in the morning paper and think about your schedule for the day before you take the plunge.

Don’t push your luck with the flannel you wore to Big Day Out in 2010. It’s done. Kaput. Finito. Get a new one from somewhere – anywhere. Your local Salvation Army will have a billion. Sentimental value shouldn’t be a bigger priority than epic moth holes and a grotty stench that you can’t clean out.

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