If you ask a menswear guy what the coolest part of his wardrobe is, the answer will usually be one of two things – shoes or outerwear. And it’s not surprising, really; these are the two places where you can really define your style with strong pieces, and where investing in something nice will offer great returns. Even if most of your wardrobe is very simple and inexpensive, some well-made, bold footwear and coats can still make it feel exciting.

A good piece of outerwear does have some advantages over footwear, though. Most notably, they take up much more real estate on your body, giving them a much larger presence. And a good piece of outerwear will be able to frame your face well, which will better portray the part of you that people spend the most time looking at. So more than just about anything else, I feel that investing in great outerwear can really define one’s style. This article is about the outerwear that I’ve come to rely on over the years – it’s a collection that I’ve built up slowly, adding about one piece per year and selling off the pieces I don’t use.

Because outerwear has such strong design elements, it’s often more of a seasonal piece than a core item in a brand’s offering. In other words, almost all of the items on this list are long gone can’t be purchased in the exact form that I have them in. If you find a piece of outerwear that you fall in love with you might want to grab it before it’s gone, otherwise you might end up with some serious outerwear FOMO (an experience most of us have likely had).

As always, here’s my normal caveat: this is by no means an exhaustive list. These are just some of the most classic pieces that I’ve found highly useful. There are many other pieces you could add, depending on your style and the weather where you live. Because I live in such a mild climate, there’s not much need for the really heavy cold- and storm-proof stuff. In short, your outerwear essentials will be a reflection of where you live and how you like to dress. Also, I thought about writing where to buy each of these styles but the article just got too long – look for that info in upcoming posts. So with all that said, here’s the outerwear in my closet.

Lightweight Field Jacket

This is the cornerstone of my collection. There are so many variations of field jackets on the market, most of which are very easy to wear. The often oversized fit makes them easy for layering, the standing collar will always help frame your face well, and the multitude of pockets make it easy to pack things for the journey ahead. This is what I reach for more than anything else – it may not have the “wow” factor of other outerwear styles, but it almost always works. There are the more military-inspired m-65 styles and m-43 styles, and then the more rugged field jacket styles as well. Get something in a nice light- to mid-weight cotton and it just might become your go-to piece.

Below: the jacket I wear more than anything else – a M-65 style field jacket from Gant Rugger in 2013 (back when the brand was making some amazing things). It’s faded, fraying, and still a favorite of mine.

Waxed Cotton Jacket

This is like the fall/winter version of the cotton field jacket – there are many similar styles, often with more rugged detailing. These are hearty and stiff, though, and are great for cool weather and light rain. Some are designed like a field jacket, while others are more motorcycle- or hunting-inspired. They’re heavy, can be a little greasy, and sometimes even smell a bit weird. But despite it all, they’re a ton of fun to wear.

Below: my beloved Twin Track from Private White VC circa 2016 – one of my most coveted pieces of clothing.

Leather Jacket

This is a whole world unto itself, one that I can’t claim to be any sort of expert in. A good leather jacket is expensive, but it’s also a piece that can elevate your entire wardrobe. I wanted something subdued and not too fashion-forward, so I went with a bomber jacket in suede. It’s easy to wear with jeans or dress trousers, depending on the look you’re going for. Like with footwear, getting a good leather jacket is important – a cheap one will look bad quickly, whereas a good one will get better the more you wear it. More rugged styles like motorcycle jackets will have more of a “badass” vibe, whereas more refined ones like mine will give off more of a “cool dad” vibe. But no matter which direction you go, you’ll definitely be omitting some sort of vibe out into the world.

Below: the iconic Valstarino from Valstar in brown goat suede, purchased this year (2019). More info coming soon.

Raincoat

It seems to rain a little less every year here, but there are always a few days that require significant protection from the elements. On those days, nothing but a good raincoat will suffice. This is certainly the least interesting piece in my collection, but a waterproof shell with a hood is just something that you need to have around. Because this piece is all about function instead of style, I look for products that can deliver on that front – waterproof fabric (duh), taped seams, a good hood, and some protected pockets to make sure my things stay dry. I also look for something that packs up small so that I can easily include it in a small bag if I think the weather might turn.

Below: The PreCip from Marmot circa 2017, a classic and affordable raincoat.

Trench or Mac

These sorts of jackets are great for when the precipitation isn’t too severe (or your time in it is limited). As a result, you can amp up the style a bit and go with something that will actually make you look cool. I love classic trench coats, but sometimes they can feel like a bit much; that’s why I opted for a single-breasted mac. It’s simple, streamlined, and looks good. I like macs in navy, but I personally would stick with classic tan for a trench. Most trench coats and macs these days are a bit on the shorter side and hit mid-thigh (like this one). That’s fine, but don’t shy away from longer coats. They’ll keep you drier and will have a lot more attitude than their cropped relatives.

Below: My mac coat from Club Monaco circa 2012 (the oldest in my collection). I replaced the buttons many years ago, and wrote about it in one of my first blog articles ever.

Top Coat

This is an easy choice for whenever you need to bundle up and also look sharp. A topcoat is like an extension of a suit – similar lines and construction, a more structured shape, and usually made from similar materials. So while I do occasionally wear topcoats a bit more casually, I think they look best over tailored clothing.

Because top coats have a very simple design, I find that it’s easy for them to look a bit lifeless. Try to find something more interesting than a solid navy, charcoal or black wool, and opt for a more interesting texture or pattern if you can. And make sure those lapels are big enough to give you some coverage when you inevitably flip them up.

Below: an amazing coat from Eidos circa 2014, made with donegal wool from Molloy & Sons.

Oversized Overcoat

If your climate supports it, a large overcoat can be an extremely versatile piece. As discussed on Put This On, an overcoat is one of those few pieces that can work well with everything from contemporary clothing to classic tailoring. They’re pretty easy to throw over whatever you’re already wearing – for me, that’s usually a casual button-down shirt and chinos or denim.

I like these sorts of coats with big collars – this is not the place for some shrunken lapels. I also like raglan sleeves because they tend to look a bit more slouchy, but that’s not a hard requirement. For fabric, I look for some texture and pattern. Herringbone is one of my favorites, but there are lots of great choices!

Below: a surprisingly awesome coat from Abercrombie and Fitch, of all places. Purchased last year, 2018.

Expanding the Wardrobe

There are so many more options than what I list here, way more than I have the time to discuss in this post. Leather jackets are a league of their own, double-breasted overcoats are one of the coolest things I’ve ever seen, and there’s so much more workwear-inspired stuff that I haven’t even touched. But if you’re just getting started, the styles above are great places to start. Figuring out what fits your lifestyle is a slow process and outerwear is expensive, so go slowly and take the time you need to invest in the right pieces for you. Before too long, you’ll be like me – accumulating so many coats that you have to build a rack just to store them.