Technically *he says pushing up his spectacles on the bridge of his nose* the most comfortable jeans for men could be… any pair. Super helpful, right? But, why is it always those battered things at the back of your wardrobe that feel the best?

As you wear denim, the fabric softens and the jeans mold to your particular uses (hence why a phone outline often appears around the pocket). As long as you have the right size, and right fit, plus you follow the Levi CEO’s guide to denim care, then they will end up feeling a part of your own body.

Sadly, I presume you’re here because the sturdy indigo cotton trousers you used to love are no longer with you. Destroyed by an oil spill? Victim to one drunken tear too many? Or, lost on an extreme trip through the jungle? Maybe you’ve tried to replace them with new jeans and you haven’t hit it off, or you wonder why your other jeans don’t quite compare?

We’re here to restore that comfort to your life with a round-up of the most comfortable jeans for men. I want you to have dapper denim to thread new wonderful memories through. Read on below for our master criteria.

Key Takeaways 

After hours of surfing the web, I can finally stand up (surfing joke) and make a bold announcement: these are the 8 comfiest jeans for men.

I’ve searched through social media, brand websites, emails, memories, and my wardrobe for these perfect critters. Overall the most comfortable jeans for men are the Asket Washed Denim Jeans. They achieve top marks by using an organic midweight 100% cotton that has been softened and washed designed to cloak you in immediate pleasure. Plus, it is available in two easily styleable tones. You can’t go wrong style-wise, and the comfort-to-quality ratio is weighted nicely.

So, what goes into deciding the most comfortable jeans for men?

The fit and style determine how it will feel on your legs, i.e. skinny, slim, straight, taper etc. Your choice here might be guided by wanting to achieve a certain aesthetic and whether that suits your body type. The size determines whether or not it’ll stay affixed to your hips, or whether the fabric will gather at your toes. Next, material. Will it be raw denim, washed denim, or stretch denim? This is in ascending order of how much time spent wearing it will take to feel comfortable.

Raw denim takes months to break in, but according to Stridewise, it will become like “a second skin” once it is. Standard-washed indigo denim doesn’t need shrinking to fit and can be comfortable straight away depending on its treatment.

This is the most dependable route to comfort, hence why I favored the Asket pair highly. Denim pants with stretch (i.e. cotton blended with elastane) will feel comfortable immediately but might not have longevity or material integrity owing to their polyester blend quality and associated low cost and build quality. Lastly, weight will affect the time it takes to feel comfortable and its durability.

The second best choice is these Levi’s jeans. Never heard of Levi’s? Boy, you’re in for a treat. This raw denim stretch-to-fit 501 is a lifetime investment and worth the time spent breaking it in.

Why it’s Great: The simplicity of these Asket washed denim jeans is what makes them so alluring. But don’t ever think that a high-quality pair of standard indigo jeans is just standard. It’s foundational, central and integral. But never standard. These comfortable jeans for men are applicable for every man and though date back to the 19th Century, always come across as modern.

How they feel: The fabric is 13 oz. organic denim is at the lighter end of the spectrum and will feel delightfully easy to wear, but not paper thin, nor overly prone to breaking.

Flaws but not dealbreakers: The aesthetic may become predictable. So, it’s important to take it as a challenge to yourself to spice your outfits around them. Remove yourself from the generic jeans-tee continuum and throw in a cashmere scarf, hiking boots, or even a trilby. (Definitely not a trilby).

Material: 13oz, 100% organic cotton, Italian Denim | Sizes Available: W: 28-38, L: 30-34 | Colors Available: 2 | Fit: Slim or Regular

Why it’s Great: These are “dad” jeans at their most authentic. Not draped from the skeletal figures of Kendall Jenner or Gigi Hadid, but worn by honest dads up and down the country day-in, day-out. There’s a vast range of sizes and dye choices meaning that every man is catered for.

How they feel: The 2% spandex gives stretch, meaning, so long as you have the right size, the jeans will be super comfortable as soon as your daddy-long-legs slip in.

Flaws but not dealbreakers: As you might have gathered from my frequent reference to dads (shout out papa James) the style is somewhat vanilla. (To achieve peak dad, try flannel-lined jeans.) But if it’s casual comfort you’re after, then these are an excellent choice.

Material: 98% Cotton, 2% Spandex | Sizes Available: W: 29-60, L: 29-36 | Colors Available: 9 | Fit: Regular

Why it’s Great: When you want a classic pair of jeans, you go to an upstanding, heritage brand. It doesn’t get much more original than Levi’s. This pair of 501s (original fit) comes in selvedge denim, meaning giving the cuff a little roll-up will bring a bit of verve to your outfit. Plus, the dark indigo means you can experiment with outerwear, smart jackets, suave overcoats and chic shirts to bring an edge to your look.

How they feel: This is shrink-to-fit denim (STF, as the heads call it), meaning the jeans will shrink 1” on the waist and 2-3” on the leg. So adjust your purchase size with this in mind. Wash in hot water three times and dry. Then, as users/reviewers suggest, it will work out fine.

Flaws but not dealbreakers: If you have commitment issues, these aren’t the jeans for you. However, the need to shrink and break in means that a lifelong bond will be formed with these iconic jeans.

Material: 100% Cotton | Sizes Available: W: 28-42, L: 29-36 | Colors Available: 1 | Fit: Signature straight fit

Why it’s Great: If you like your comforts fast, cheap and sexy (easy now) then these Uniqlo jeans are for you. The brand claims it has the feel of sweatpants, suggesting super soft wear and muchos muchos stretch. They achieve this with the polyester, Lyocell and Spandex blend. These heady heights of comfort are rarely found in a pair of jeans.

How they feel: I would suggest reserving these jeans for casual occasions. The fabric doesn’t have the aesthetic quality of a good raw or selvedge denim. They are reserved for when you need a snug feeling and ease of motion.

Flaws but not dealbreakers: As well as your mind being ripped open by coziness, let the lower price point prepare you for the potential for rips on the fabric too.

Material: 70% Cotton, 20% Polyester, 9% Lyocell, 1% Spandex | Sizes Available: XS-XXXL | Colors Available: 4 | Fit: Slim

Why it’s Great: The brilliance of these Ralph Lauren stretch jeans is by combining the worn-washed denim with an elegant stretch. The slim style means it won’t get in the way of everyday tasks, be it cycling to work, lifting heavy objects, or sprinting for the bus.

How they feel: “What the hell is elasterell-p?”… I just read in my notes. It is the proper name for stretch polyester. Part of this definition requires that elasterell-p can stretch 100% of its original length, and then rapidly and quickly revert to its original constitution. Bosh. You can see how this property added to denim would be comfort-enhancing.

Flaws but not dealbreakers: This pair of jeans excels at what it does: casual, stylish, washed denim. The lighter hue means it’s not as versatile as a darker indigo wash and can’t breach into more formal attire.

Material: 94% cotton, 5% elasterell-p, 1% elastane | Sizes Available: W: 28-42, L: 30-34 | Colors Available: 1 | Fit: Signature slim fit

Why it’s Great: This pair of raw denim jeans oozes cool. The “seagull” painted flick on each buttcheek will mark you out as “in the know”. It gives off a whiff of streetwear, but only subtly, so you can incorporate the style into other looks easily too.

How they feel: The raw denim needs commitment. It might be months before Tokyo’s underground street drifting community gets to see you rocking these bad boys. Text a few pals, explain the situation, and hang in there. Once you’re there, it will be soft, malleable and moreover, individualized for as long as the denim lasts.

Flaws but not dealbreakers: If you want instantly comfortable jeans because you need to work in them, or just simply refuse to participate in delayed gratification, then these jeans won’t be for you.

Material: 100% Cotton | Sizes Available: 28-38 | Colors Available: 1 | Fit: Carrot

Why it’s Great: ‘Cuz they’re interesting. The two-tone style suggests reused/surplus fabrics when in reality, both dye tones are constructed from a blend of virgin and recycled cotton. The aesthetic is both misleading and true. I love it. And that rightly sums up this pair’s mysterious allure. Plus, the fray at the hem gives it an intentionally “model-off-duty” look that only a white vest and a pair of tiny-framed glasses could compliment.

How they feel: It has a casual bent. However, its more fashionable appearance means that you can indulge it with luxurious overcoats, derbies, and billowy jackets to achieve a formal nonchalance (which is a delicious oxymoron don’t you think?)

Flaws but not dealbreakers: If you couldn’t care less about looking devastatingly chic, then turn the page.

Material: 80% Cotton, 20% Recycled Cotton | Sizes Available: W: 28-34 | Colors Available: 1 | Fit: Straight-Leg

Why it’s Great: Japan Blue jeans are produced in Kojima, Japan (shockingly). This town is home to many vintage selvedge looms and also the famous “Jeans Street ”. These two facts should give you some inkling as to the dedication, passion and honor that Japan Blue gives to its denim. These chic mid weight white jeans are for denim heads who don’t mind splurging on the best Japanese denim.

How they feel: Despite being raw, the one wash and midweight fabric will give it a slight softness to help the break-in period.

Flaws but not dealbreakers: In addition to all of the raw denim complications, the white tone is a scary one for some. I find white jeans difficult to style. Despite saying that, when it works, they can look so debonair. For some reason, an indigo denim jacket or a green jacket (chore, cord, linen) really goes well and so do brown suede shoes. Generally, a pair of white jeans suits the warmer months for its light reflective and cooling properties. If you want to be super aerated wearing denim, bust on a pair of baggy jean-shorts, AKA, jorts.

Material: 100% Cotton | Sizes Available: W: 28-38 | Colors Available: 1 | Fit: Relaxed Taper

Buying Considerations for Comfortable Jeans

Material

This is key to your decision-making process in terms of comfort and suitability. Raw denim is unwashed, untreated, and not shrunk. It is therefore stiff at first but over time it will morph into your unique patina, will soften and become super comfortable. Remember that raw denim will shrink to size after purchase. Regular denim is non-stretch by nature but will have been softened, treated and shrunk to size. It will also mold to your body after a while and will continue to get softer and more comfortable. Just DON’T wash it too often, if at all if you can avoid it.

Style 

This is determined by design and color. The Evisu painted “seagull”, or the two separate fabric tones used by Axel Arigato are good examples of unique design.Color usually sits on the spectrum of indigo (since that was traditional in denim), black or white.

Fit

Fit has a large role to play in determining the jeans style too. Options include but aren’t limited to skinny, slim, straight, baggy, loose, wide, tapered, carrot, or flare. At the moment, folks are opting for straight or slightly baggy fits to mimic 90s/00s trends.

Why you should trust us

I’ve been modeling for top brands for over a decade and writing for top fashion publications for over five years. In that time, I’ve come to know the industry very well. For this review, my direction was twofold: stretch material and raw. I scoured the internet. Used my memory of brands, and my own humble humdrum experience of wearing denim on the reg. I then sought the most stylish and comfortable pieces online, always ensuring there was enough stock for the punters (you).

Final Verdict 

Remember that most jeans by top brands can be comfortable. I emphasize the quality of produce and care for your jeans while they’re under your supervision. Get the fit right.

Decide how long you’re willing to wait for them to achieve peak comfort. Then search out your preferred style. We’ve chosen the Asket Washed Denim Jeans because they have a choice of two likable tones, come in an immediately soft but still quality organic cotton denim, and have a conventional fit. They are the perfect casual and comfortable jeans for men.