This Fall Denim Trend Ended My 10-Year Relationship With Skinny Jeans

As a millennial, my adolescence was shaped by skinny jeans, especially low-rise skinny jeans. Though the style didn’t fit my new curves, I wore them exclusively. After all, everyone else did. High-waisted skinny jeans came around eventually, and I celebrated, converted, and started feeling more comfortable in denim and in my body. When the TikTok Cheugy Wars of 2021 happened and Gen Z users declared skinny jeans (and side parts) over, I dug in my heels and swore fealty to skinnies. Like many of my fellow millennials, I was skeptical of mom jeans and wide-leg jeans, but, as baggy, wide-leg jeans become one of fall 2022’s biggest denim trends, I have a confession to make: Fellow millennials, we were wrong. Wide-leg jeans — specifically high-waisted, wide-leg jeans — are the best and I’m never going back.

I tried three different pairs of wide-leg jeans on my journey to embracing this fall denim trend. Each pair was relaxed, even baggy, through my thighs down to my ankles. They were all high-waisted and, while the volume ranges from almost straight-leg to Y2K parachute pants-adjacent, they all had one thing in common: They changed my silhouette, making parts of it bigger, which, in turn, made my body take up more space. Until I saw myself in the mirror for the first time in a pair of wide-leg jeans, I thought this was a problem.

Somewhere between high school and college, and without me even realizing it, I developed a singular fashion goal: to make myself appear as small as possible. I refused to even consider wide-leg jeans because I didn’t want to wear anything that would expand my silhouette, take up more space, or make me look bigger than I actually am.

While I’ve been aware of the more obvious ways I’ve worked to shrink myself — in my career, in my relationships, and with disordered eating habits — I didn’t realize that this ingrained desire extended to my wardrobe until I pulled on jeans that broke the cycle. I was shocked to find that I felt *hot* in wide-leg jeans. The style not only worked with many of the cropped and fitted tops I already own, but they elevated every look I paired them with.

Wide-leg jeans are also comfortable, even with mega-high waists. There was no need to unbutton them during brunch and no wriggling them off my ankles at the end of the day. They’re comfortable, and feeling comfortable in them made me, in turn, feel more confident. To reiterate, they made me feel hot AF. Ahead, you’ll find the three pairs of high-waisted, wide-leg jeans that convinced me, a millennial, to break up with my skinny jeans for good.

Light Wash High-Waisted, Wide-Leg Jeans

I might love Old Navy’s Extra High-Waisted Wide-Leg Jeans more than any other pair I own. They cost $45, but make me feel like a million bucks. I wear between a size 6 and a size 8 and tried both sizes in this style. Jean sizes are notoriously irregular and I don’t trust ‘em, but I was pleasantly surprised to find that both sizes fit. The size 8 is baggier throughout — great for a Y2K pop star fashion moment — and I’m wearing the more fitted size 6 in the photo below.

The size 6 fits me snuggly at my waist and gives me just the right amount of volume around the ankle. There’s a fine line between wide-leg jeans and oversized jeans à la Hot Topic in 2004, so if you’re considering this pair and want them to hug you, stick to the smaller end of your sizing spectrum.

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These jeans have stretch, but also provide the level of support around the waistline that you’d expect to feel in non-stretch denim. I ate wings and drank many beers in these jeans, but these jeans made space for my organs and my carb intake.

Distressed Black High-Waisted, Wide-Leg Jeans

I may never have gone down what I now know is the dark path of the skinny jean if I had had a pair of jeans like this in middle school. Sure, I wore every troubled seventh grade poet fashion staple (aka black polyester parachute pants), but these jeans marry the worlds of street style and Hot Topic-inspired emo energy.

Windsor’s Effortless Edge Wide-Leg Denim Jeans are definitely the baggiest pair of high-waisted, wide-leg jeans I tried. They were also the pair that got me started on this quest to fill my life with baggy denim. As soon as I tried on this $47 pair of light stretch jeans, I knew I could not rest until my closet included multiple wide-leg options.

Because Windsor’s jeans come in odd numbers, I opted for a size 9 — I have too many memories of trying to squeeze my 15-year-old body into a size 5 (when what I needed was a size 7) to ever go near either of those two numbers again — and I’m very happy with the fit.

These jeans sit at my natural waist and don’t squeeze or pinch when I sit down, something I didn’t know I needed until I wore jeans that didn’t constrict my digestion or breathing. Go figure. Currently, this exact pair of jeans is only available in a size 13 on the Windsor site, but the brand’s Distressed, But Well Dressed Boyfriend Jeans give the same vibe in a dark blue wash and are available in more sizes.

Dark Wash High-Waisted, Wide-Leg Jeans

While The Perfect Vintage Wide-Leg Jean in Leifland Wash from Madewell is the closest to straight-leg, the brand still offers the baggy good times of wide-leg jeans. At $138, they’re the priciest pair on my list and also the jeans I was most nervous to try on because the denim felt so thick and I expected almost no stretch. Instead, I was pleasantly surprised to find them just as comfy as all the other wide-leg jeans I wore.

A month of wearing high-waisted, wide-leg jeans has taught me a lot about being comfortable. While, at 31, I’m more comfortable than I’ve ever been in my body, I still have a long way to go toward making the choice to feel comfortable in my clothes. I call it a choice because I’ve always felt varying levels of discomfort in skinny jeans, whether they squeezed too tightly after I ate, cut into my sides, or got stuck on my legs when I tried to take them off.

Wide-leg jeans are so comfortable that I never had to think about them — except to admire how good I looked. It’s amazing to find out how much space you have for other, better thoughts when you’re not worried about how your clothes are constricting or limiting you. It took me way too long to learn this lesson, but I’m glad I did, and I’m glad I finally found a style of jean that makes me feel proud to take up space.