I grew up in Hammond, Indiana (the town where A Christmas Story is based). And the scene where Randy is bundled up like a tick about to burst, his arms whirling uselessly at his sides, is basically my entire childhood.
After so many winters of enduring total bodily confinement for months on end, I'm not a fan of breaking out the parka or topcoat unless it's below freezing, snowing heavily, or the tail end of November.
Living in Chicago today, I have a minimum of three months that require such cumbersome outerwear, so I'll be damned if I'm going to stuff myself into a parka before it is absolutely necessary.
Combine these brutal winters with hot, humid summers lasting from May until October and my opportunities to wear a light jacket are that much more fleeting.
Autumn is a sacred time for style guys, so I jump at the first chance I get to wear a light jacket and ride it out for as long as possible.
Choosing a light jacket
Summer wardrobes can be pretty boring and winter wardrobes tend to favor survival over aesthetics, but the light jacket category that accompanies the autumn season is rife with possibilities.
Materials are numerous, colors are plentiful, and designs are limitless. Some of these options really aren't outerwear, but pass as such, nonetheless.
Base your decision on your local weather and your professional and social environments.
Below are some broad categories to help get you started when looking for that perfect light jacket.
I go into the details of selecting the best leather jacket in my free 10 Timeless Wardrobe Essentials eBook, so I'll just focus on style here.
I'm a fan of moto and bomber style leather jackets. These are going to be most versatile as they're plenty edgy, without going into the wannabe rockstar arena.
They also have plenty of personality so you don't have to worry about missing out on any of the cool factor.
Since you're likely to spend a pretty penny on a quality leather jacket, it makes sense to treat this as an investment and go with a fairly minimal style in a versatile color.
You don't want to be kicking yourself a year from now when you realize that you bought a $400 jacket on a whim, and have since outgrown the style.
Recommended Leather Jackets
This is the epitome of a light jacket.
You'll sometimes find leather jackets in this style, but I'm focusing on the modern nylon variety.
These jackets are perfect to pair with your entire casual wardrobe and are just right for autumn, warmth-wise.
The short body allows for unrestricted movement and the elastic cuffs, waist, and collar are comfortable and great at keeping the wind out.
Recommended Bomber Jackets
It rarely seems to drizzle in my neck of the woods. But when in rains, it rains.
I'm talking about monsoon-type rains that will have you soaked to your skivvies by just sprinting from the front door to the car.
Needless to say, some type of waterproof outerwear is essential, especially if your main modes of transportation are a good pair of boots and a transit card.
A jacket with a hood and loads of pockets will be very functional, while a sleek option, sans hood will be the obvious choice for professionals.
Don't be afraid to go with a little color here.
You don't need to go knee-length yellow rain slicker bold, but a little color never hurt anyone on a dreary day.
Recommended Rain Jackets
What these light jackets lack in legitimate warmth, they more than make up for in rugged coolness.
For best results, buy a jacket in its raw, unwashed state and break it in on your own. That's the best way to get a perfect fitting and looking jacket.
If you love the look of a denim jacket but are after a little more warmth, a sherpa-lined denim jacket would be perfect.
When pairing a denim jacket with jeans, avoid the Canadian tuxedo look and ensure the jacket and jeans are different colors and/or stages of break-in.
Recommended Denim Jackets
In the middle of summer, I always rant about the cruelty of traditional menswear, arguing that a dress shirt, tie, and jacket are best suited for 50 to 60 degree days.
Following that logic makes a sport coat the ideal light jacket.
To emphasis its function as a light jacket, rather than a permanent component of the outfit, try popping the collar if the weather is brisk.
You won't look like a douche bag if you flip the collar to combat the elements – they're actually meant to be worn that way, after all.
Heavier fabrics and patterns work best as a light jacket. I wouldn't try this as readily if the sport coat resembles an orphaned suit jacket.
If you aren't quite sure what that means, the distinction between a sport coat and a suit jacket is outlined in my free 10 Timeless Wardrobe Essentials eBook.
Recommended Sport Coats
All buttoned up, a cardigan looks much like a normal sweater and will come off as a component of the outfit.
Popping the collar and/or leaving it mostly unbuttoned will strengthen the outerwear illusion.
I like to wear cardigans in the same manner as I used to wear a hoodie. It's a grab-and-go kind of deal.
Another tip is to wear your cardigan over another sweater, like a merino wool v-neck. This move will make it instantly stand out as outerwear, because who layers sweaters like that?
Shackets, overshirts, or shirt jackets are cut like a denim jacket but made of heavy shirting material.
I like these jackets in thick flannel, corduroy, wool, chambray, and canvas.
They can be found in both lined and unlined options.
Wearing this type of light jacket over another collared shirt will help it appear more like outerwear, rather than a peculiarly thick button up.
My grandfather is one tough SOB, and in his younger years, wore one of these with a quilted lining exclusively during the winter (in Chicago). He didn't even button it!
How to Make it Work
As soon as the weather dips below balmy, hold off reaching straight for the heavy duty parka.
Instead, ride out the mild weather in a light jacket for as long as possible by (a) using light layers under your clothes and (b) adding a hat, scarf, and/or gloves as needed to reinforce the jacket.
Do this and you'll be able to extend the time before the cold, cruel winds of winter force you into outerwear that is strictly survival-based.
Stay cozy, my friends.
All the best,