By Manish Puri

In part one of this guide, I provided a brief history of chambray and why it became the de facto choice for work shirts, before turning my focus to shirts on the market that are reproductions of traditional US work shirt models.

In this second part, I’m covering chambray shirts made by brands that tweak and update the historical templates – shortening them for modern sensibilities, removing a pocket, taking in the waist etc – which can make them more contemporary, versatile and easier to pair with tailoring.

I should add that the guide is still focused on casual shirts – those with pockets, contrast stitching, roomier cuts and softer, smaller point collars.

The Anthology Workman Indigo Raw Chambray Shirt – $200

Of all the shirts in this guide, The Anthology’s Workman is the one that’s closest to a dress shirt.

The general fit, whilst not slim, is certainly tailored when compared to the more overtly workwear options. (You can see that in the flat lay images – the majority of the shirts are cut straight whilst The Workman is shaped through the waist). The collar band sits higher and is slightly stiffer. And the colour is also stronger than the more washed-out versions, which I think helps make it appear a fraction smarter (although it too will fade nicely over time).

On the other hand, the smaller collar points, contrast stitching, locker loop, flapped chest pocket and vintage cat-eye buttons (in mother of pearl) are all features inherited from the shirt’s workwear forebears, and soften the formality.

I think this union makes The Anthology shirt the most versatile choice in this guide, as it can quite effectively pull a double-shift as a (fairly) casual shirt that sits comfortably with tailoring, and thanks to the collar band, even a tie (above).

The other appealing element of all The Anthology’s shirts is they’re sold on an MTO basis (and, as a result, take three weeks to make). There’s a helpful video on their website explaining the process, but essentially it involves selecting your collar size (unusually for casual shirts, The Anthology’s collar goes up in quarter-inches for the most common sizes) and then adjusting the waist, back length and sleeve length by up to 4 cm from the default measurements. That’s over 8,000 size permutations (my maths teachers would be so proud). 

I think it’s an ideal choice for readers that don’t want to go down a full MTM/bespoke route but need to make a few common tweaks to get a better fit.

Whilst this guide is focused on the classic blue chambray, it would be remiss of me not to point out that I also have The Anthology’s vanilla chambray shirt (above) which I absolutely love (and actually wear more often than the blue). 

It’s off-white in colour and textured with tiny vanilla-seed like flecks. A great piece for tonal dressing and an easy way to ‘warm up’ an outfit in lieu of a white shirt.

Bryceland’s Teardrop Chambray Shirt – £225

If you pop into one of Bryceland’s stores or their online shop, you’ll find not one but four chambray options. Each one with a distinctive design and silhouette, taking inspiration from a specific period in American history.

The half-zip shirt (£249) is a fuller-cut option that works well as a layering piece in winter or worn dégagé – unzipped and untucked with a nonchalant roll of the cuffs –  in the summer. 

The design perhaps partly inspired by the Big Yank Zipper Ace shirt (above right) that was released in the 1930s for “those that like the quick convenience of putting on a shirt in two seconds flat” (you can read more about that brand in part one).

The sawtooth westerner (£249) recalls the cowboy shirts of the 1950s with a broad chest that contours into a nipped waist. 

The denim version was the first Bryceland’s product I ever saw and purchased, and it instantly hooked me on the brand; although it does have an exacting silhouette for anyone (like me) that is straight through the trunk. There are days, usually those after I’ve spent the weekend at my Mum’s being force-fed samosas, that I would love the waist to be just a fraction more forgiving.

The USN chambray (£195) is stylistically quite similar to the Buzz Rickson 1940s model featured in part one of this guide. The main differences are the buttons (Bryceland’s are white) and the extra stitching through the left chest pocket to create a separate pen pocket. 

The other significant difference is fit – specifically length. While the Buzz Rickson shirt was a bit shy in venturing past the upper thigh rendering it potentially ‘untuckable’, the Bryceland’s USN has no such reservations. It runs long, Peter-Jackson-Extended-Cut long (for example, size 38 and 40 are around 35 inches), which is faithful to the original style of these shirts.

Bryceland’s USN shirt is sold in both raw and washed chambray.

If this appraisal so far makes me sound like a sartorial Goldilocks – this one’s roomy, this one’s long, this one’s a little squeezy on my tum-tum – then can I say the teardrop chambray shirt is just right.

Patterned after one of Bryceland’s co-founder Kenji’s vintage Lee shirts, it’s a comfortable and well-proportioned shirt that I think most clothing brands today would typify as “classic fit”. 

I chatted with Bryceland’s London manager Ben, and he thought, based on the manufacturer’s label, that the Lee shirt dates to the 1950s. That seems consistent with this ad from 1951 (below) where the khaki shirt in the middle looks to be identical to the teardrop.

I loved the easy simplicity of the design – symmetrical, neatly scalloped chest pockets and small gathers of fabric under the yoke are really the only embellishments. Combined with the solid construction and double stitching of the seams, it meant I had little hesitation in taking a shirt (size medium) home with me – even though I was only meant to be trying it on for this guide!

The teardrop chambray is also available MTO (meaning you can have it made up from hundreds of cloths including some really nice linen-cotton chambrays – a great option for readers in warmer climes) and MTM (which allows for a wide range of adjustments to the shoulder, sleeve, body, waist, etc) – both services have a 20% surcharge to the RTW price. In the first part of the guide, a lot of readers were asking about anywhere that offers custom work shirts (not chambray dress shirts), with most guys crying out for longer sleeves in particular. For those chaps, I’d recommend the Bryceland’s teardrop chambray.

Drake’s Bleach Blue Cotton Chambray Button-Down Popover Shirt – £275

A button down, popover shirt is a foundational piece within the Ivy tradition. If you need proof, Jason Jules’ superb book Black Ivy is stocked with photos showing men in both short- and long-sleeved versions – including Miles Davis in a terry cloth popover (below left). 

At the same time, a popover style (especially in chambray) harkens back to the very earliest US work shirts and overshirts for sale at the turn of the 20th century – like the ones in the Sears Roebuck & Co catalogue from 1897 shown below right.

And so, to my mind, this shirt is a genuine Ivy-Workwear hybrid, making the Drake’s one of the more interesting styles that I found on my hunt: a great alternative option for those readers that already have a more orthodox model.

Because popovers need to pass over the shoulders when you put them on/take them off, I’ve found it can help to have a touch more room in the body than you might for a full-placket shirt.The medium did fit – but in the same way that I used to like my dress shirts to fit a dozen years ago. Alas I’m no longer in my 20s and I’m not going for a night on the town at Tiger Tiger. 

The excellent staff at Drake’s had anticipated this (they clearly know their product) and had already discreetly deposited a size large in the fitting room – an altogether better option for me with a bit more room in the arms and belly.

So, unless you like a  particularly trim fit, I’d size up in this shirt.

Honourable mentions

Every year I see the Kenneth Field chambray shirt (above) land in The Merchant Fox’s shop, and every year I inexplicably delay purchasing it just long enough for it to sell out.

Admittedly, I’ve not actually seen the shirt in person, but the slubby texture of the Japanese chambray always catches my eye. The style is similar to the USN designs we’ve already covered, but with a flap chest pocket on the right hand side.

I’ve been told by The Merchant Fox that there’s limited manufacturing of this piece. However, a small restock is expected in the summer, so if you too like the look of the shirt I’d recommend signing up at their mailing list to avoid disappointment.

Manish is @the_daily_mirror on Instagram

Read Part One in this series on chambray here