Ever since that Obama “Dad Jeans” debacle back in the Aughts, intelligent men across America have been shamed into spending  $100, $200, even $300 and up on  what are basically, well, just blue jeans.

Now, before you think I’m looking down my nose at you, I confess I am no stranger to falling for the latest Retro-Fit, Down-Wash, Side-Hustle, New-Crush, Best. Jeans. Ever.

But this Fall, when it came time to replenish jean drawer, I decided to take a step back from the high-priced madness and issue myself a challenge:

Could I find jeans I wouldn’t be embarrassed to wear on Instagram (or at least out of the house)… for under $40?

To find out, I headed to Amazon to conduct my Lazy Man’s Shopping Spree. Upon arrival, I type in the search term “Men’s Jeans” thinking this made sense. It did not.

It turns out there are no fewer than 51 brands to choose from, I kid you not. Even after narrowing the search to “Men’s Jeans Under $40,” and only choosing only those with “Prime Free Shipping and Returns,” I’m still waist deep in denim.

No, I will not apologize for that pun however unintentional it was.

Be sure to look for this Free Returns option before adding to your cart. It’s awesome.

So here is my first, visceral takeaway: I’m an idiot!

There are so many options available in every possible cut, wash, color, and size for under my target price of $40 I can’t believe it. And right off the bat I can see that there are at least some I would wear without hesitation.

Ugh. I take a moment to mourn the loss of innocence (and dollars!), and then press on.

I start off in familiar territory and wade into the classics first – Lees, Levi’s, and Wranglers. I cart a few likely prospects and move on to a few brands I’ve never heard of –  Carhartt, AXEL, Perruzo. None of which make the grade, but am curious enough about a pair of jeans made by Stetson, the hat people, that I add them to my cart.

Just like ordering at Starbucks, the winnowing process is helped by knowing a little bit of the terminology. Terms like “Relaxed Fit,” “Loose Cut” or “Comfort Fit” are all code words for “Baggy Dad Jeans,” and are, in my case at least, grounds for immediate dismissal.

Most of my currently deteriorating jean-stock are in the “Slim Fit, Straight-Leg” category, so these are what I focus on primarily. I have a pair of “Skinny-cut” jeans which I vacillate back and forth on whether or not I like them, but this day I ignore them all. Emboldened by the Free Shipping, I do decide to mix it up a bit and throw in a couple pairs of Boot-Cut jeans in for good measure.

MBM tip: Once you find something that looks promising, immediately select your size. There’s nothing more frustrating than falling in love with a particular style only to find they’re not available.

So far I have focused on Cut, but in my opinion the number one feature that separates fashion-forward jeans from the rest is the Wash. Yes, over-stitched pockets, just-so rips, and randomly placed rivets are departure points, too, but for me, Wash is what truly defines a jeans style and even utility.

Dark Wash jeans, for example, are considered “Business Casual,” but the same cut in an overly-faded or distressed wash are suddenly night and weekend wear only. Same jean, completely different purpose.

So what made it into my cart? Have a look:


For nostalgia’s sake I stuck to some known brands – Levi’s, Lees, and Wranglers. As mentioned earlier, I threw in a pair of Stetson’s for curiosity’s sake. And just to “go low,” I added in the $14.91 Key Apparel jeans.

My winner?


The Levi’s, of course!  I kinda knew I would like them going in – they are after all what I wore as a kid. I didn’t think I would like them as much as some of my more expensive jeans, but the truth is I do. And not because they only set me back $34.99 (ugh, kill me now!)

As for the rest of the jeans, a close second were the Lee’s and the Wranglers. They fit well, but the wash was not quite as fashion-forward so the Levis won out. I could go back and see if the others had similar washes – they probably do. The Stetsons were a bust, very plain, pouchy crotch, just kinda meh over all.

And my $14.91 Key Apparel Jeans? Sadly they were the wrong size, but I could tell that would not have mattered. They were no bueno.

So, did succeed in finding stylish substitutes for my pricey denim precursors? I’d say unequivocally Yes!

But you know how I really know I did okay? When I showed my wife my finds, she nodded her approval and then said, “Huh, maybe I should do that next time, too.”

Ahh, the sweet sound of success!

EDITOR’S NOTE: This is not a sponsored post as much as I wish it was. When I become super popular and have sold out completely, I expect the views and opinions shared here will still be 100% my own.

If you like this post why not let me know by joining my mailing list?