Whether you’re in bomb cyclone territory or more temperate parts of the country, the ideal lightweight jacket (or two!) is an important element because you can layer up or down depending on temperatures, all while maintaining style and a comfortable temperature. There are a million different versions in all manner of materials, but until you’ve completely nailed all the essentials, I recommend sticking to the classics for versatility, style and ease of wearing. No matter which one you choose or what the weather app on your phone is telling you, you can layer up confidently (t-shirt, collared shirt, sweater, whatever) for anything from work to a night out.
The Bomber Jacket
Also sometimes known as the MA-1 and tracing its lineage back to the uniform jackets designed for military pilots in World War II, the classic style and functionality of a bomber remains just as strong today as it was back then. Featuring a zip front, elastic waist and cuffs, and a low-profile collar, you can find stylish versions of the bomber in every conceivable material, from nylon and wool to cotton and suede. I absolutely love the versatility of a bomber jacket, and as I’ve said before, every man, regardless of age or body type, should have one in his closet.
outfit details here
Who Should Wear It
All body types and ages look great in bomber jackets – as long as it fits well – close to the body with arms and shoulders fitted like the above picture.
How To Wear It
A casual staple that’s infinitely versatile, the Bomber looks right at home with everything from a t-shirt and denim to chinos and a chambray or oxford shirt. Make sure the shoulder seams sit properly, almost exactly like how your suit jacket or blazer should fit and know that a bomber jacket that fits properly should stop right around your waist. Most bomber jackets are slightly shorter in the back, too, so don’t think something is wrong if you notice that. A longer bomber jacket tends to look odd and sloppy, so avoid it if you can.
For outfit ideas, see this article, as well as points 3 & 4 in this article/video.
The Trucker Jacket
Just like it’s close cousin the Bomber, the trucker jacket was born out of utility and remains a classic style piece to this day. Typically of shorter length and hitting around the hip/waist, the workwear-inspired trucker jacket often features a button or zip front, fabric-covered collar, and handy flap pockets on the front. I like all types of materials for trucker jackets but you’ll most commonly find them in sturdy waxed cotton or canvas (to protect against the elements), denim, and nylon.
outfit details here
How To Wear It
Another one my go-to casual recommendations, I love a trucker jacket with denim and desert/work boots. It looks stylishly masculine but still polished enough to be worn over a collared shirt without looking like you’re commuting to work on a horse.
For my favorite trucker jackets and the best ways to wear them, check out this article.
The Field Jacket
Going by many names (M65, Utility Jacket, Safari Jacket), this essential is just another example of how functional military-inspired designs still look sharp and stylish today. It’s slightly longer length should hit just past the hip and it commonly features multiple sets of pockets for extra utility when you’re on the go. The Field Jacket is a great protector against the weather yet light enough for the Spring’s rapidly changing temps, so look for it in cotton and nylon versions. Forest or Olive green colors are more traditional but I’m a big fan of navy (my favorite), darker browns or grays, as well.
Who Should Wear It
Stockier or larger men. The multiple pockets help break up your large top half and give a slimming appearance.
Who Shouldn’t Wear It
If you’re a slimmer guy and not 100% confident in how to wear this, avoid it because it’ll can make you look slimmer and like you’re swimming in pockets and fabric. I see this mistake more often than not. So when in doubt, skip it.
How To Wear It
Layer it over a cashmere sweater and an oxford or even your favorite dress clothes to add a bit of contrasting ruggedness to a polished look. Of course, it’s always perfect for your weekend morning coffee runs with t-shirts, jeans or tailored sweats too. I’d avoid wearing it with chino pants because the fabric weights are too similar and you’ll look like a 70’s action star pretty quickly. Ideally, you want something heavier on the bottom – jeans or wool trousers.
For my favorite field jackets and best ways to wear them, check out this article.
The Harrington Jacket
I’ve talked about my love of the Harrington jacket before, and for good reason, this jacket strikes that perfect sweet spot between casual and sporty and goes with pretty much anything. Look, if it’s good enough for style icons like McQueen, Elvis, and James Dean, it definitely deserves a place in your closet. The Harington blends a slight preppy edge with the functionality of a windbreaker and most often features a light cotton or nylon shell, zip-up front, and barrel button collar. Whether on the links, out and about, or heading to drinks, the Harrington has you covered. 
Who Should Wear It
All body types and ages look absolutely fantastic in a Harrington.
How To Wear It
The Harrington’s preppier look and vibe pairs perfectly with staples like chinos, t-shirts and button-ups, but it just as easily transitions to a casual evening out when layered with a light sweater, dark denim and sneakers or loafers. For more in-depth details, see this article/video.
The Denim Jacket
While it’s at home on the range or in a 50’s movie star’s vintage Porsche, the denim jacket can be just as stylish and useful to you on your own city streets. A classic for a reason, the denim jacket has seen a recent resurgence to staple status now that denim is pretty much everyday wear. While this short, button-up jacket doesn’t offer a ton of warmth, it’s vintage throwback style, when paired with a crisp white t-shirt or layered over a light cotton sweater, more than makes up for it.
outfit details here
Who Should Wear It
Everyone! It looks right at home on men of all ages and body types. The only caveat is if you’re an older man (50’s and above) you may want to avoid lighter colors, as it tends to look a little “trying to dress too young”, so stick to darker indigos or black if that’s you.
How To Wear It
Properly pulling off the Canadian Tuxedo is a very dicey (impossible?) move, so keep it simple and pair with chinos and black or dark denim, or opt for colors like grey, black, indigo, or light-washed denim. On the fit side, it needs to be tight in the arms and body and stop at the upper part of your waist, so keep it trim and short to avoid looking boxy or like a 90’s R&B music video backup dancer.
For more details, check out my more in-depth article/video here.