Written by Ivan Yaskey in Essentials on the 9th January 2020

One is no fun. Of course, we’re talking about winter jackets. While a single style is limiting, gets kind of dull, and might even wear out prematurely, the weather’s relatively all over the place this time of year. As such, the garment you don when it’s hovering just around freezing won’t be the one you put on to shovel out the driveway, and the same jacket won’t always have the properties needed to stay dry through icy, stick-to-the-pavement rain. Yet, with guys opting to clear out cluttered wardrobes, you can have too much of a good thing – or, at least, too many items where you might only wear a jacket once or twice a year. So, you’re neither finding yourself short nor wishing you had fewer overcoats, here are your basic pieces of winter outerwear:

Leather Jacket 

It’s a classic – and not just for the cool factor. As we’ve ruminated many times here, leather jackets end up being one of the most practical items out there – just as long as you know how to layer. A quality garment – and not something that’s flimsy or strictly fashion – is known to block out the wind. That’s why you’ll often spot motorcycle riders donning a leather jacket and even a matching set of trousers. As well, the natural animal hide keeps body heat close – and that’s even before a quilted lining or similarly lightweight insulation has been added. A quality garment, too, will be treated to withstand repeat exposure to the elements, like rain and snow. On the subject of layering, the right fit – read: not too skin-tight – gives you enough room to put on a flannel, fleece, or quilted vest below, thus doubling the warmth you’ll feel on those below-freezing days.

Peacoat 

To the office – or out for the night – nothing’s more on the money than this Navy-originating garment that, in its truest form, is fully constructed out of wool. Yes, you’ll come across flimsy cotton blends out there, but the peacoat excels on multiple fronts. One, at its core, it’s a low-level tech garment that never truly looks techy. Wool naturally repels moisture, lets your skin breathe to a degree, traps body heat, and won’t hold onto odours. Aside from these features, the double-breasted front and above-the-knees boxy fit offer enough room for a blazer or cardigan underneath, and overall, the jacket delivers perfect business-to-smart-casual vibes, no matter if you’re sporting a full suit or chinos and an Oxford shirt underneath. Added to this, the extra room also lets you wear a second, lighter jacket underneath, be it denim, a bomber, or even fleece. Its somewhat rugged character, from this angle, shakes off its office-only impression and gives you an everywhere-anywhere jacket that’s nearly always good to go.

Overcoat or Trench 

Yes, the history is different, but these two garments essentially serve the same purpose: a little more coverage and significantly more formal style than a peacoat and all other options on this list. The trench coat comes with more military baggage – and a set of epaulets might even hit that home further – and typically has a belted waist. But, if you work in finance or law, or find yourself attending black tie or similarly formal events with some regularity, anything less makes a too-casual and ill-informed impression. The key, here, is deciding which materials and constructions suit your day-to-day activities. Wool, of course, exceeds other options in spades – unless it’s cashmere, which is an investment unto itself. On the other hand, some trench coats share features with rain coats – like water-resistant construction – but don’t have the full body of wool. As such, consider supplementing your coat with a warmth-retaining midlayer like fleece, shearling, or Sherpa underneath.

Puffer or 3-in-1 Parka 

By definition, these two are different, but in terms of functionality, they share many characteristics – mainly, insulation and water-resistant properties. On the economical side, a puffer by itself does all of these things – plus, several techy styles pack up into a single interior pouch, making them ideal for traveling or hiking this time of year. Yet, a little more substance and coverage are needed, and that’s where the parka comes in. Although some models come with extra bells and whistles – for instance, multiple hidden pockets and features built for the ski slopes – a quality parka keeps the insulation close, adds a stronger, perhaps abrasion-resistant exterior, and throws in a hood for good measure (and much-needed coverage) into the mix. The 3-in-1 format simply makes this concept more adaptable, giving you a puffer, a sturdier shell, and a hood you can attach based on your needs.

Winterized Version of a Casual Jacket 

Everything’s being winterized these days, from trusty jeans to high-top Vans. In a few years, don’t be surprised if you start seeing winterized tank tops and board shorts. As such, it’s about time we started spotting winterized bombers, blazers, and denim jackets. The format’s rather predictable: Heavier exterior materials, such as wool, leather, or corduroy, supplemented by a quilted, shearling, or fleece lining for insulation. A darker colour palette screams, “It’s not fall anymore, but I’m not waiting around for spring.” As such, if you can’t give up the bomber or trucker silhouette yet and aren’t in the mood to layer, seek out a winterized version of your transitional go-to.

We feature the best outerwear for men such as Leather Jackets, Peacoats, and Puffer Jackets in this guide to 5 Must-Have Men’s Winter Coats.