I Currently Own 29 Pairs of Jeans, But These Are the Only 7 I Actually Wear

It’s been 14 years since living together in New York, but my ex-roommate still loves to tell the story of "Judith’s Jeans.” My bedroom in Apt. 27 was essentially a glorified closet, yet a quarter of the small space was taken up by a mound of jeans quite literally from floor to ceiling.

Fast-forward 14 years to my apartment in L.A., and not much has changed (aside from more square footage). My denim obsession remains resolute. What can I say? I love jeans, and when I find a pair that fits well and looks good, it’s hard to resist. I currently own about 29 pairs (some gifted, some scored secondhand, some I scooped up in sales, and some investment jeans I’ve splurged on), yet I fully acknowledge that owning this many is not exactly normal (and, to be honest, a tad embarrassing). I came up with this article idea after cleaning my closet, and as I sifted through my denim collection, I realized even though I like all of them, there are actually only seven I love to wear on repeat. Go figure!

best-comfortable-jeans-288707-1597863250594-main

(Image credit: @joiedejude)

So below, I’m highlighting my seven favorites that I wear all the time. Not only are they comfortable, but their silhouettes hit me right, they flatter my body, and I love the quality. Now, I’m off to Goodwill!

best-comfortable-jeans-288707-1597861396816-main

Citizens of Humanity: Charlotte High-Rise Straight Jeans
(Image credit: @joiedejude)

Citizens of Humanity is one of my favorite denim brands because of its excellent quality and fit. (As you'll see, they appear on my top-seven list more than once.) While they tend to be on the pricier side, they're worth every penny, as I wear them so darn much. The Charlotte is the perfect straight-leg silhouette, and the high rise hits my waistline just right. I also love the vintage-inspired wash that combines well with everything in my closet. Moreover, they're surprisingly super comfortable despite being non-stretch.

best-comfortable-jeans-288707-1597873789926-main

(Image credit: @joiedejude)

Shop:

best-comfortable-jeans-288707-1597863581133-main

Citizens of Humanity: Olivia High Rise Slim Ankle Jeans
(Image credit: @joiedejude)

Okay, another Citizens of Humanity pair coming at you—and I could seriously rave about these jeans all day. If you're looking for a stretchy pair with a slimmer cut (but not über-skinny), then these are ideal. First off, they are supremely comfortable. (Thank you, elastane.) This particular wash is perfect for so many scenarios. It's easy to dress up with heels and a nice top or pair with a chic blouse for work, and it also looks amazing with a simple white tee and sneakers. I find the high-waisted ankle-length silhouette is ultra-versatile.

best-comfortable-jeans-288707-1597863659389-main

(Image credit: @joiedejude)

Shop:

best-comfortable-jeans-288707-1597864077189-main

Levi's: 501 Jeans
(Image credit: @joiedejude)

I absolutely love the vintage look and feel of these classic Levi's 501s. I actually scored these at a vintage market, but after a quick search, they're pretty easy to find online. These are rigid and non-stretch, so at first, they may seem a little uncomfortable, until you wear them in. I don't usually get compliments on my jeans, but when I wear these, I always (graciously) receive a ton.

best-comfortable-jeans-288707-1597872345382-main

(Image credit: @joiedejude)

Shop:

best-comfortable-jeans-288707-1597867146559-main

H&M: Super Skinny High Jeans
(Image credit: @joiedejude)

When it comes to skinny jeans, I tend to wear two on rotation. This gray wash from H&M and a Madewell pair (which I'll talk more about below). This pair from H&M is super stretchy, comfortable, and fits really well. They're easy to throw on with blazers and boots or with sneakers or sandals. Plus, you can't go wrong with the price!

best-comfortable-jeans-288707-1597867690050-main

(Image credit: @joiedejude)

Shop:

best-comfortable-jeans-288707-1597867734883-main

Madewell: 9" Mid-Rise Skinny Jeans
(Image credit: @joiedejude)

The other pair of skinny jeans I wear a ton are from Madewell—another denim brand I love. These super-soft black skinny jeans are extremely versatile and easy to move around in. I like styling them with knee-high boots in the colder months and minimalist sandals in summer.

Shop:

best-comfortable-jeans-288707-1597868495073-main

Agolde: Vintage High-Rise Flare in Absolute
(Image credit: @joiedejude)

I've really loved the resurgence of the '70s flare and wide-leg silhouettes, which have been trending for the past few seasons and are set to be huge for fall. Agolde's vintage high-rise flare jeans are my favorite, as the silhouette is wonderful, and they're made of 100% organic cotton, which is super soft to the touch.

Shop:

best-comfortable-jeans-288707-1597869640000-main

Paige: Noella Straight Caballo Inseam
(Image credit: @joiedejude)

I've been leaning into casual, loose-fitting jeans a lot more lately given our current circumstances, and Paige's Noella Straight style has been my go-to. It has a cropped silhouette and is slightly distressed, giving it a relaxed feel. But the best part? It's seriously comfortable.

Shop:

Shop More Jeans I Love:

Up next, the seven biggest jeans trends of fall 2020.

Judith Jones
Senior Fashion Market Editor

Judith is the senior fashion market editor at Who What Wear and has worked in fashion for nearly a decade. Judith started on the Shop Who What Wear team, creating content and managing a team of merchandisers for the Who What Wear shopping app. She later crossed over to the editorial team, where she shares the coolest, most desirable fashion market finds and brands in her shopping-focused stories and social takeovers. She has become one of the top affiliate earners during her six plus years at Who What Wear. Before working in fashion, Judith was a TV host on the PBS travel show Globe Trekker (airing on Netflix and Amazon Prime) and shared her passion for travel and food. She studied at the prestigious London Academy of Dramatic Arts as well as Stella Adler Studio of Acting in New York. She later studied fashion merchandising and design, which laid the foundation for her career in fashion.


Read full bio