The 5 Best “Heritage” Style Shorts for Rugged Guys

This is a really niche topic, but since this site is about the kind of apparel that I look for, we’re doing it: the best heritage shorts.

What Does Heritage Mean?

We’ve published an entire article about what heritage means, but generally speaking, it refers to vintage or vintage-inspired casual American clothing for men, and oftentimes it’s similar to what working class guys used to wear to perform labor: like Goodyear welted leather boots, thick selvedge denim, duck canvas pants, wool chore coats, and so on.

Heritage shorts to many sound like an oxymoron because generally speaking, heritage guys don’t like shorts. Back in the day, guys didn’t really go outside their home or the beach in shorts, so there are a lot of heritage guys who simply refuse to wear them. (See the comments on my first video about shorts for examples!)

But I’m Australian, and while I live in New York City, I have not shaken my need to wear shorts when it’s hot. This put me on a quest to find the best shorts that are at least “inspired” by heritage fashion, so I’m looking for:

  • rugged durability
  • something that’ll age well, and
  • no elastane, spandex, bamboo, or modern materials meant to increase comfort or make things stretchier. 

(This, is the main downside some see with heritage clothing: while it looks great, it’s not stretchy or super comfy.)

One final note: given these are small companies, they’re often low on stock or sold out. If it’s not too late in the year, I suggest doing a Google Image search for the company and product name. That does a better job, in my opinion, of showing other online stores selling the products and whether or not they’re in stock.

That’s why in addition to linking the manufacturers, I’ve put as many links as I could find for third party vendors like Standard and Strange, Uncrate, Stag Provisions, Hard Pressed, Franklin and Poe, and other good places to look at for more from heritage brands.

grown and sewn ranger shorts

1. Best Overall: Grown and Sewn – Ranger Short ($125)

In my opinion the best shorts for that are the Ranger Shorts from Grown and Sewn, a small heritage brand that sell out of Red Wing Heritage in New York City as well as online.

They make a lot of cool shirts out of materials like chambray and twill, but what they’re known for is their 9 ounce canvas, which they make with a custom finish that makes it fade and acquire wear and patina a little like denim. The shorts don’t patina the same way as their famous Foundation Pant, but with heavy wear the shorts will get a little  variation in color and consistency, and it also softens as it ages.

The fabric is woven in the USA and the shorts are made in the USA as well, and if you think the classic Camel version of these very burly shorts are too reminiscent of camp counselor shorts, note that you can also get them in red, blue and a natural ‘stone’ color that’s always sold out when I want a pair.

Note that I had to size up to a 33, I normally wear 32.

[Shop the Ranger Short here]

buck mason officer short

2. Best Value: Buck Mason – Officer Short ($85)

If $125 is too steep for those Grown and Sewn shorts, I encourage you to check out what i consider the best value heritage shorts: Buck Mason’s Officer Short. You’ll note names like ranger and officer in a lot of these shorts because they’re meant to be reminiscent of what law enforcement officers used to wear — in Buck Mason’s case, the military.

In almost all of my videos, especially the first two years of this channel, I wear Buck Mason’s excellent henleys. The brand is a bit more about minimalism than heritage, but the slubby twill these Officer Shorts are made from is an iconically heritage fabric.

Slub refers to irregularities in the appearance caused by uneven thickness of the warp,  and while these aren’t as slubby as a lot of very intentionally slubby jeans like my Samurais, you can still notice a streaky appearance in this fabric.

Slub might technically be a flaw, but it’s a flaw that many guys crave: it means it’s more human, it’s made in a more old fashioned manner. Many fabrics  (especially denim) used to have more slub, but now most companies consider them faults, even though they don’t detract from the durability of the fabric. 

buck mason officer short

These shorts are not as burly as Grown and Sewn, but they’re still fairly hefty. It’s 100%  twill, a pretty tough and densely woven kind of cotton fabric that I’ve found stretches a little more easily than canvas. But despite the heritage approach — which typically means it’s a very informal — these dress up fairly easily.

[Shop Buck Mason’s Officer Short in 3 colors here]

UES Duck Shorts

3. Best Japanese: UES – Duck Short ($180)

UES’s Duck Short is primo stuff, and I’d say it’s the best Japanese heritage short. Even though it’s based on clothing from America’s Golden Age heritage fashion has a dedicated following in Japan, where the country’s famous penchant for exacting attention to detail and generational craftsmanship has manifested some of the world’s best boots, jeans, and in this case, shorts.

UES is a small Japanese label founded by Chuji Matsumoto in 1994. The name comes from the English word “Waste”, which is meant to be because Matsumoto wants you to make full use of each garment for as long as possible before discarding it. (That’s another big feature of heritage apparel: it lasts for a really long time, and looks cool as it ages.)

[Related: 7 Reasons Japanese Jeans Are So Expensive]

UES Duck canvas Shorts

UES’s duck shorts cost $185m, partly because they’re totally made in Japan, also because it’s woven on old fashioned shuttle looms which produce this low tension fabric that has a really nice depth and texture. When you combine it with the reactive dyes, you get a short where the texture will increase and the colors will become enriched as they age.

Duck fabric is really popular for workwear and most of Carhartt’s most popular work pants are made with duck. It’s woven with two yarns together in the warp and one in the weft and it’s super strong and won’t tear.

Add to that triple stitching, reinforced fabric, and buttons made from none other than buffalo horn, and you’ve got a pair of shorts that’ll last at least ten years and look better as it does. 

[Use code STRIDEWISE5 for a discount on the UES Duck Shorts here]

freenote cloth deck short navy

4. Best Drawstring: Freenote Cloth – Deck Short ($160)

If your goal is to never buy another pair of shorts, these might be up your alley. This is a military inspired heritage Deck Short from Freenote Cloth.

freenote cloth deck short brown

The deck short stands out for these unique curved pockets that I think are really nice; I saw one reviewer say on their site,

it’s the kind of design flourish that makes the shorts instantly recognizable without being flashy.

The pockets also have snaps to keep your belongings secure, which would otherwise be a downside to watch out for when you’re sitting down in these. The fabric is Bedford cord, which is a real nice balance of soft and strong, and everything comes from Japan and is sewn in the United States.

[Shop the Deck Shorts here]

stevenson overall and co rangefinder

5. Best Cargo: Stevenson Overall Co. – Rangefinder Short ($285

Lastly we’ve got the best cargo shorts. I know that cargo shorts are a pretty ’90s thing to wear, however they were popular in the ’90s because they were military throwbacks — and military throwbacks count as heritage to me.

stevenson overall and co rangefinder

So if you want the kind of shorts guys used to wear, these ones from Stevenson Overall & Co these are inspired by those worn by the US Army in the 1960s. They’ve got a relaxed military silhouette and they’re 100 percent cotton, made with double gauze fabrics: a soft, airy fabric made from two layers of cotton gauze fused together. This gives you the loose open weave of gauze but it drapes better and it’s not as transparent. 

[Shop the Stevenson Overall & Co Shorts here]

Honorable Mentions

Those were the best five I found, but I came across so many cool other shorts that I’m going to add a quick ‘honorable mentions’ section here for shorts that are way harder to find, but are worth Googling around for.

3 sixteen - Drawstring Short

3 sixteen – Drawstring Short

These are really cool, they’re indigo dyed shorts that will fade like jeans. They’re 12 ounces per square yard, so fairly thick but not for denim, and they’re made in the USA with a denim from the famous Nihon Menpu in Japan. Made with a 5×5 weave instead of 3×1, it’s got a coarser texture than you usually see in denim but they’re soft and ready to wear from day one.

[Look for these on 3sixteen or Franklin and Poe]


Rogue Territory – Fatigue Short

I wouldn’t call these denim shorts jean shorts and they’re not traditional, but I love the combination of very irregular, neppy denim with an elastic waistband and a gusseted design. At 9 ounces, the denim is very cool and lightweight and I think they’re worth adding to your wardrobe. 

[Look for these at Uncrate and Hard Pressed if they’re not on Rogue Territory


Stanray – Fat Short 

These ones are made in Turkey, which you might not count as heritage, but it’s made with military grade sateen — a nice, soft, 100% cotton fabric. I’m a big fan of the fatigue aesthetic, which is reminiscent of military style shorts but with a softer material.

[Shop Stanray here] 

taylor stitch trail short

Taylor Stitch – Trail Short

These look just like a combination of Grown and Sewn and Buck Mason, the first two entries on this list. I love the stitched down front pocket bags for a really informal heritage-y look that’s based on vintage military fare. They’re 100% cotton, of course, and they come in a variety of slubby fabrics. But they’re pretty much all sold out at the moment.

[Try your luck with the remaining sizes at Taylor Stitch]

iron heart west point shorts

Iron Heart – West Point Shorts

This is a brand with a lot of serious heritage cred and I’ve actually reviewed their jeans before here. These shorts are based on the standard issue uniform trouser fabric worn by cadets at West Point Military Academy, so they come out like chino shorts made with 11-ounce right hand twill fabric made in Japan.

[Shop the Iron Heart jeans here]

Greasepoint Workwear - Easy Short

Greasepoint Workwear – Easy Short

The last honorable mention I wanted to include are Greasepoint Workwear. These shorts, they write, are

Inspired by some climbing shorts from the 90’s, this short is designed to be rugged, unrestricting, and easy to wear.

Made with “camping, gardening, biking, hiking, and enjoying the sun in mind” these shorts have a built in belt and a really boxy fit to improve mobility. Some are made with Japanese denim, some are made  from 10-ounce pique fabric from a Japanese mill that’s a lot like canvas, but it has something of a sheen. (If that puts you off, note it dissipates with washing.)

I’m not a huge fan of these shorts but since you don’t see that many heritage workwear companies selling shorts, this might be a variety you like. 

[Shop Greasepoint Workwear here]


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Wrapping Up

I spent so much time on this article and I’m almost positive that practically no one will read it, such is the disdain that heritage guys tend to feel for shorts, but if you’ve read this far I hope you’ve found something that you like!

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Nick English

By day: Manhattan-based journalist with reporting experience on four continents, published in Vice, Men's Health, Popular Science, and a bunch of other places.By night: ravenous consumer of anything and everything related to high end men's boots.Stridewise is where I nurture a maniacal obsession with footwear and share my findings. Say hey: [email protected].

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