Prime Day(s) is in full swing, and there is no better time to stock up on jeans from the king of American denim.
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Levi’s more or less invented blue jeans as we know them and has stood as the industry standard for the past century. No symbol is more associated with stylish denim than the little red tab.
The San Franciscan denim distributor is not only a titanic cultural force but also dominates the market with more fits and fades than any competitor.
Photo by Brad Lanphear for Gear PatrolLevi’s releases an avalanche of indigo annually, which can be bought directly from the brand or through a litany of wholesale retailers. None of those third-party distributors offers a better deal on the king of American denim than Amazon during Prime Day.
Prime Day 2025 is stocked with Black Friday-busting deals on the best men’s jeans, ranging from the OG, always appropriate 100% cotton 501s, to the slouchy and stretchy 541s.
I even threw some denim jackets in the mix cause I just couldn’t help myself with these deals.
Jeans
Levi’sLevi’s 501 Jeans
It’s not the original Levi’s design, but it is by far the most influential. The designation dates back to 1890 and has gone through various iterations, but the current cut matches the overall consensus on how jeans ought to fit: a bit loose in the hip with a slight taper from the knee to the ankle. Two defining characteristics of the modern 501 are that it has to be 100% cotton and has to have a rivet fly.
Specs
| Fabric | 100% Cotton |
Levi’sLevi’s 514 Straight Stretch
The 514 is a modernized version of the 501. It has a slim-ish fit, with a slightly loose hip and a bit of a taper from the knee down. The two models even have the same leg opening width. However, the 514 has a dash of Elastane in the fabric for some stretch, a slightly lower rise (i.e., sits lower on the hip) and a zipper fly.
Specs
| Fabric | 99% Cotton, 1% Elastane |
Levi’sLevi’s 517 Boot Cut
Western style has never really gone out of fashion, but in 2025, it is as prevalent as ever in menswear. You don’t have to rock a cowboy hat and snap-button shirt to pull off boot-cut jeans. They are a great middle ground for a looser-fitting silhouette that isn’t baggy (i.e., sloppy) in the waist and hip. It even looks great with a blazer—just ask Ralph Lauren and Robert Redford.
Specs
| Fabric | 100% Cotton |
Levi’sLevi’s 511 Slim Stretch in Natural
If you’re going to stray from blue when buying a pair of jeans, “natural” is the way to go. It is the perfect color for summer, but it works year-round. The tawny off-white goes by various names from brand to brand, but it is most frequently referred to as “natural” because it resembles the color of undyed cotton denim. You can wear this color with anything, making it just as useful as a pair of blue jeans.
Specs
| Fabric | 99% Cotton, 1% Elastane |
Levi’sLevi’s 505 Regular Fit
Levi’s calls the 505 “Regular Fit,” which is both unhelpful and kind of a perfect description of how it fits. It is a bit looser than the 501 and straight all the way through, not baggy, but in no way form-fitting. You can think of the 505 as the stereotypical “Dad Jeans,” but that’s a look nowadays.
Specs
| Fabric | 100% Cotton |
Levi’sLevi’s 511 Slim Fit Jeans
You can think of the 511 as the “Millennial Fit,” with a snug hip that has a slight taper all the way down to a hem that rests on top of your shoes. A quick styling tip: you typically will want to go with a shorter inseam on a slim fit jean vs. a loose fit because of how the leg’s opening rests over shoes. A slim fit will bunch up more if it is the same length as a looser fit.
Specs
| Fabric | 99% Cotton, 1% Lycra Elastane |
Levi’sLevi’s 541 Athletic Stretch
The fashion industry’s new preferred term for loose fit is “athletic.” The 541 is ideal for gentlemen with full hips and thighs who want to have some shape to their jeans and not be swimming in fabric. It also offers some stretch for a little extra give.
Specs
| Fabric | 98% Cotton, 2% Elastane |
Jackets
LevisLevi’s Type III Trucker Jacket
The Type III Trucker Jacket, arguably the most iconic outerwear ever produced by America, is so tightly associated with Levi’s that the term Type III comes from how the brand denoted the generations of its denim work jacket. From truckers to rock stars, everyone looks good in one of these. Just go with a 100% cotton version so it will last longer and age better.
Specs
| Fabric | 100% Cotton |
Levi’sLevi’s Denim Harrington Jacket
The Harrington jacket is one of the most versatile and stylish pieces of lightweight outerwear ever invented, second only to the trucker jacket. Making one from denim further magnifies both of those attributes. You don’t often see a denim Harrington jacket, but Levi’s is the best place to get one.
Specs
| Fabric | 100% Cotton |
Levi’sLevi’s Sherpa Lined Type III Denim Jacket
This is the winterized version of the iconic Type III denim jacket. It has a polyester sherpa fleece lining, which mimics shearling wool on a sheepskin leather jacket, but for a much more affordable price.
Specs
| Fabric | Shell: 100% Cotton, Lining: 100% Polyester |
Brad Lanphear is an associate editor at Gear Patrol covering watches and style. Before joining the publication, he previously wrote for Heddels and Men’s Health. Now, he’s on a never-ending quest to find the perfect pair of Japanese denim.
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