The Dealmazing Blog

The Most Comfortable Jeans For Men Under $100

I've got a little problem.  I have such a hard time finding jeans!  I used to be a Levi's guy, but then i went to the store to try on what I thought were my favorite fit, and they were completely different than I remember.  UGH, yeah first world problems I know, but if you're like me, finding jeans can be a CHALLENGE.

That's why I set out to find the best jeans for under $100.

In my quest, I actually was looking for the lowest cost options, since I really don't like spending close to $100 for any piece of clothing.  I'm a guy, but this guide can really be used for both men and women, as I sought out the denim brands with options for both genders.   

So, what am I looking for exactly?  Well, it has to be comfortable---numero uno in my book.  Most jeans today are using a stretch fit material, which I'm mostly ok with, so the jeans of today are actually a lot more comfortable.  Two, I want durability.  I had a great pair of JCrew Factory jeans that I loved, but they kept ripping random holes in them only after a couple of times wearing them. While it pays to get nice quality, some brands are just made with cheap material to begin with.

So here are some ideas for denim brands that won't break the bank and are super comfortable.

1) American Eagle - Extreme Flex Jeans - Retail $49

These jeans changed my perception of comfort in denim.  Fit--like a pair of sweatpants.  Quality - fantastic.  Note the Slim fit is pretty tight and would define that as more of a 'skinny' jean.  The slim straight (as shown) is still pretty form fitting, yet not very tight and with the stretch provides a lot of room.   

Good thing is that these jeans are on sale all the time, so you should be able to pick up a pair for closer to $40, and you'll be pleasantly surprised with the style, the comfort and the price. 

PROS: Ridculously comfortable and often can get these for closer to $30.  Great value!

CONS: The fabric is a little bit thinner than a normal denim, which is expected with the strech material--so expect these to be a bit more comfortable in the summer months, but overall longevity is probably not as a great as a true pair of denim.

2) Abercrombie & Fitch Kennan Straight Jeans - Retail $78

Abercrombie has really stepped up their game of late as they've completely toned down their ridiculous branding.  So for the most part--a lot less of those Moose LOGOS!  Overall, I have been pleasantly surprised with their jeans -- (note my wife loves her A&F jeans too).  They have several attractive washes, and the fabric overall seems pretty durable.  Note that jeans are often on sale here, so be on the lookout for different promo codes and signup offers.   I like the Kennan (straight) which is more of a slim fit.

PROS:  Very Comfortable and very inexpensive if you find the right deals.  I like the fit and they give a good amount of stretch.

CONS: Given the stretch fit, I've heard some complain of these completely blowing out but I haven't had that issue.  The sizing at A&F is a little confusing, so I'd recommend visiting a physical store to try these on.


3) Hollister Epic Flex Slim Straight Jeans - Retail $49

Yep, i'm talking about that teen/tween brand Hollister.  But,'s a secret. They have some great jeans.  And not surprising as A&F owns Hollister, so consider this your budget secret surprise brand.  And these are at the moment currently on sale for $25, so consider this for NOW, the super duper budget brand.  

PROS:  Very stylish (i got compliments a few times actually!) and very form fitting.  Based on the average pricing (close to $25) probably the best bang for the buck amongst the group.

CONS: Fit is similar to the jeans from A&F, but in comparing the two, the stitching and fabric feel a bit infrerior to Abercrombie.  Sligihtly noticeable, but for the price, not really a game changer. Fit can also be inconsistent, so (as embrassing as it may be to set foot in a store) try to try these on. 

4) Levi's 511 Slim Fit Performance Strech - Retail $75

Here's the deal with Levi's -- the sizing is extremely inconsistent.  Not sure what the deal is, but I've tried on jeans that I currently own at the store, and the fit is completely different. 

**(Side note if you're looking for a fit guide on Levi's jeans this is a super helpful article)

So, make sure you go try these on before buying online as I prefer to get these in the store.  Macy's has a lot of options for Levi's as does Nordstrom if you can't make it to an actual Levi's store.

PROS:  Great quality, and great fit (if you find the right one), plus the style is one of the best.

CONS:  Annoyingly inconsistent sizing, they never seem to be the same, so make sure you go to the store to try these on when you buy them.