The Dude Society

An Online Magazine for Guys.

How To Buy An Awesome Casual Jacket

Seems like a shame when you dress up nice to go out, now I mean nice casual not nice formal, and finish off your outfit with your old fleece or a hoodie… it just ruins the overall picture. This is just one of the reasons you need at least one cool jacket. When I say “cool” jacket, I mean a casual jacket that fits you well and makes you feel badass. If you follow my suggestions, it will probably get you compliments as well.

Start with fit

If something doesn’t fit you properly it isn’t worth buying. I’m going to venture out on a limb and say, when left to their own devices, most guys buy articles of clothing that are at least one size too big.

So, as a first step, for any jacket you try on, start by trying one size smaller than you normally would. If you think you’re a Large, try a Medium instead. If you think you’re a Medium, try a Small. Also remember, sizes in different brands don’t always match up, so just because you’re a Large in one brand, doesn’t mean you’re a Large in everything.

Depending on what clothes a guy is used to wearing, it’s pretty easy to confuse something feeling tight and actually fitting properly. For example, a properly fitting jacket should hug your shoulders fairly snugly, meaning the shoulder seams should land right at the edge of your shoulder. If you are used to wearing shirts that are too large, you might have a knee-jerk reaction and think the jacket is too tight when it’s not.

The fit in the shoulder area is of the utmost importance, because if the shoulder area is too big, the whole thing will sag and look huge on you. If a $300 jacket doesn’t fit you properly, it might as well have cost $20. That’s not to say a jacket has to cost a certain amount, I’m just making the point that getting the right size will make it a good investment, no matter the cost.

Find the right material

You have quite a few options when deciding what material your new jacket will be: cotton, canvas, nylon, leather, and even linen are all great options.

  • Cotton will probably be the most breathable and easiest to clean.
  • Canvas, or waxed canvas, won’t breathe as much as cotton but waxed canvas will give you a cool, leather like look for less money and with less bulk.
  • Leather is classic. Whether it’s now or down the road, you should probably acquire a great leather jacket. Leather can range from reasonably priced to incredibly expensive.

A traditional “biker” style jacket is made from leather, but over recent years many designers have made variations of biker jackets in all sorts of weights and materials. I use a biker jacket as an example because it is a pretty consistent go-to cool jacket style. Pictured is a biker jacket by John Varvatos Star USA in cotton and linen.

Selection of a material may come down to personal preference, but there are a few quick things to consider.

  • Weight – Where do you live and when do you plan on wearing your jacket? If you live in LA and plan on wearing your new jacket during the day, you might want a lighter material. If you live in NYC and want a jacket to wear on fall nights, something a bit heavier is probably better.
  • Consistency – If you generally dress very casually and/or wear casual shoes or sneakers, you’ll probably want to stick with a natural fiber jacket, as opposed to leather. I know this is a bit vague, but my point is this: despite how nice that $1,500 Prada leather jacket is, if it’s going to look out of place with the rest of your wardrobe, you shouldn’t buy it.

Choose the color

If you have all sorts of outerwear, you can afford to have pieces for specific occasions or even for specific outfits. If, however, like many people, you’d rather invest in a small number of more versatile pieces, you need to do a bit more planning.

If you’re buying a canvas biker jacket, for example, forest green or bright red probably aren’t good choices. Ideally you want a neutral, versatile color. If you’re buying a leather jacket, it will often be black, which is versatile to an extent. However, if you also wear a lot of brown clothing or shoes, a black jacket isn’t a good choice. On the other hand, a gray jacket can be worn with both black and brown, so that might be your best choice. The same goes for many darker shades of blue.

Decide on budget and designer

You have a lot of choices when it comes to designer and cost. A jacket can be $50 from the Gap and a jacket can be $2,000 from Louis Vuitton, so you need to find your comfort zone. If you’re going to get a lot of use out of this jacket, spending a bit more than your normally would will probably be worth it.

Below are some sample images from

Left to Right: Hugo Boss ($345), Theory ($495), John Varvatos ($998), and John Varvatos Star USA ($498)

Everyone’s style is a bit different, but John Varvatos, Theory, Michael Kors, and Hugo Boss are great places to start your search. They have high-quality pieces at a range of prices. I’m partial to the first two, as almost all of my outerwear come from those two labels, but there are many great labels and designs that will fit you and your budget.

Go forth and shop

As I’ve suggested in the past, a good strategy is to go try stuff on to figure out what style and designer works best for you. Since your own sense of what’s best on you might be skewed, taking along a couple female friends might be a great idea. If you take my advice about size/fit very seriously, you won’t be disappointed, especially when people start complimenting you.

About the author

Jamie is the Founder of The Dude Society and a New York City based web designer & developer. He really likes telling people how to think, act, and dress.

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2 responses to “How To Buy An Awesome Casual Jacket”

  1. Jeff E. Guy says:

    It's not just jackets. Most guys buy shirts that are too big. A shoulder seam is supposed to stop at the, um, shoulder. If your seams are cutting across your bicep, your shirt is too big.

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