An Argument For Choosing Made-To-Measure Shirts, Always

Boss Hunting style content of late has been sporadic, to say the very least. Neither myself, nor the wider team is particularly inspired by any fashion brand at the moment – aside from Aime Leon Dore – but I’m not just not prepared to spend the money, or the postage to get it here.

COVID has compounded an ever-pressing casualisation of our wardrobes but also shifted our spending, prioritising our home environments over our personal appearance. People just seem to care less about ‘image’ coming out of lockdown and I think that’s a good thing – a great thing if it eradicates the menswear influencer for good.

Regardless of how casual the workplace gets, quality tailoring will never cease to be timeless, we just need to look at new ways to work it into our day to day wardrobe, and a made-to-measure shirt in a textural fabric or with a mao collar, for example, is the perfect place to start.



In a desperate attempt to do just that – and revive my dwindling interest in menswear – I decided to take part in the recent ‘Archive Sale’ from Drake’s. Even the brand I thought I couldn’t fall out of love with, left me discouraged after failing to fulfil my whole order.

While Drake’s deprived me of the ‘Navy Waxed Cotton Belted Winter Stable Jacket’ they did send out a button-down oxford and donning it for the first time reconfirmed a revolutionary realisation – an off-the-rack shirt will never come close to anything made-to-measure.

I have, or at some point have had, cotton and linen button-down oxfords from the likes of Country Road and J.Crew in my wardrobe, and while they serve their purpose well with sleeves rolled up, I often question my decision not to spend twice the money and have something made for me, especially when it comes to wearing my sleeves down.

I recently bit the bullet and opted for two casual tailored shirts from the team at Oscar Hunt, one button-down in linen and one in denim – both destined for boozy lunches, not boardrooms. Even despite adding an extra inch or two to my gut over Xmas, the fit of each, compared to anything I own from any brand, is so better suited to my body, I simply had to pen this article.

Fellows, stop wasting your money on expensive, brand name, off-the-rack shirting, be it formal or casual. For $115 less than Drake’s, $140 once you add shipping, Oscar Hunt will fit and make a shirt for you, then go to the ends of the earth to ensure it’s a perfect fit. Nothing about custom-tailored or made-to-measure is left to chance, unlike unboxing something with arms too long, collar too tight, and chest unbecoming.

At their starting price of $199, you’re almost a whole shirt ahead at Oscar Hunt and I can guarantee you, you’ll be a whole level of confidence ahead, knowing that you’re putting your best foot forwards in the most flattering garment you own.

Make it your mission in 2021 to support an Australian tailor and order yourself a made-to-measure shirt, I promise you won’t look back.



While you’re at it, read our 5 summer suiting tips from Trunk Tailors Founder Jack Liang.