Continuing our recent discussion of jacket replacements - chores, Tebas, safaris and the like - I've shot two of my favourite overshirts in order to talk about different types, and how they can fit into a wardrobe. 

The buffalo-check shirt above is typical of a first type: a heavy shirt you can layer over a T-shirt or even a sweatshirt, but could just about tuck in as well. 

Most are flannel shirts, like this, in a brushed cotton - the kind beloved by fans of Americana, who perhaps picture themselves in the woods somewhere, with a thermal underneath and a pair of sturdy work boots.

It's a style that's also been co-opted by various other genres over the years though, including bikers and the general nineties grunge vibe I grew up with, which demonstrates its versatility.

The second overshirt, above, is of a thick felted wool and is more akin to a woollen jacket. 

This type is still cut like a shirt - front placket, sleeve cuff, chest pockets - but it’s more likely to have a straight hem, and there's no way you could tuck it in. It's great layered under a coat, but underneath you'd usually want a knit or a long-sleeved shirt. 

Mine is a little unusual, being an old Boy Scout shirt that's at least one size too big for me - I like wearing in a slouchy, oversized style. But similar pieces from the likes of Pendleton are common in vintage stores, and outdoor brands such as Filson offer them today.

Those modern brands will often clearly separate the two types: Filson has its flannel shirts and, separately under outerwear, Jac-Shirts.

But it can be hard to tell vintage models apart online, such as on the ‘shirts’ category of a Broadway & Sons for example. The best thing to do there is try and get a sense of the thickness of the material, by looking at the images of the collar or cuff. Some also have a give away like a partial lining. 

While these two types of overshirt are similar in style, and are both heavier than a regular shirt (the biggest reason they work untucked), they're different in how they fit into a wardrobe, with the latter more akin to a piece of outerwear. So I think it's useful to consider them as two different categories. 

Both are definitely at the casual end of our spectrum of jacket alternatives, however. They have no structure, little shape, and a straight front with nothing like a lapel to break it up.

As a result they’ll be relaxed, weekend wear for most PS readers, and that's certainly how I wear them - with jeans or chinos, boots or tennis shoes, T-shirt or a sweatshirt. 

They're robust pieces of clothing, which look better the more they're washed and worn. That buffalo check of mine, for example, is incredibly soft after its years of wear, and I love how the black on this kind of cotton fades to grey, while the red tends towards orange. 

They’re a good choice for those readers that ask about clothes to wear with their kids - they can have many things spilled on them, be washed frequently or simply scrubbed, and look nicer for it. 

I largely wear overshirts unbuttoned. I find if a shirt is untucked and completely buttoned up it starts to look like a big, long block that isn't that flattering. 

If I do button them for warmth, I tend to start with the button in the centre of the chest (as above) before adding others around them (below). 

Even if buttoning all the way up to the chin, the bottom couple are normally left undone, which helps break up that block of pattern/colour. Heavy use of trouser pockets helps too.  

(I feel there's a whole series of articles here, on 'how to wear' rather than ‘what to wear’. Rolling sleeves, popping collars, buttoning on a cardigan etc.)

A couple of other points that I anticipate might come up in the discussion below. 

Overshirts work untucked because of their heavier weight, which means they don’t flap around and look like a regular shirt. Someone asked recently whether I’d wear an oxford shirt untucked, and I wouldn’t, personally. I can see it as a style, but it’s not mine. Most of the time you’re going to look better with it tucked in. 

Linen shirts in the summer are a little different because everything is loose and flowy, and probably because being untucked has an obvious functional purpose. 

In terms of how much it’s worth spending on overshirts, the thing to pay for is the material - no fancy handwork, no extra detailing. Vintage versions are often great for this, if you don’t mind heavier ones being a little scratchy. Look out for those Americana styles or military ones like a CPO. 

Among new brands, outdoor ones like Filson or RRL are good sources. Every fashion brand will do an overshirt, but usually the material is overfinished and not that dense, meaning they won’t wash and wear in as well. 

The Japanese repro brands all do good models, particularly when there’s more of a biker aesthetic - see shirts at Rivet & Hide from the likes of Iron Heart and The Flat Head. American Classics carries new Pendletons, and The Merchant Fox some nice wools and moleskins.

All clothing shown:

• Vintage buffalo-check FiveBrother flannel shirt, from The Vintage Showroom
• Vintage red-felt Scout shirt, from John Simons
• Heavyweight grey sweatshirt from The Real McCoy’s, Ball Park model, medium
• White T-shirt from PS, the Tapered Tee, large
• Vintage jeans, Levi’s
• Suede boots from Edward Green, Cranleigh model, 8.5E
• Steel chronograph watch, Omega Speedmaster MkIV, tonneau case

Photography: Alex Natt @adnatt