The Most Comfortable Denim Pieces for Any Occasion!

When it comes to becoming a fashion staple, few fabrics can match denim. This classic fabric looks fashion-forward even with a simple plain white T-shirt. (Just ask Beyoncé, who highlighted the pairing in her Levi’s ad, which was an instant hit.) Of course, not all denim is created equal: in fact, many cuts of this fabric can feel stiff and tight. With that in mind, we set out to find the most comfortable denim on the market and found revolutionary cotton terry fabrics with prints that look like the richest blue denim, super-stretchy, waist-hugging silhouettes, and vintage-inspired shirts and jackets that become more comfortable every time they are worn.

All of this suggests that there’s never been a better time to refresh your denim wardrobe – or, if you’ve ditched denim in favour of athleisure, then take a fresh look at denim fabrics. Next, let’s take a look at the 15 most comfortable denim pieces.

Optical Illusion: Rag & Bone Miramar Sofie Full Length Wide-Leg Pant

Can you believe that these perfectly draped jeans are actually printed like this terry cloth sweatpants? The back pockets, seams, and rivets are all elements of professional printing, while belt loops and front pockets are practical. And the best part? These “jeans” look classic, but on the inside they feel like your most comfortable sweatpants.

Comfort Classic: Levi’s 90s Trucker Jacket

TikTokers consider Levi’s 90s trucker jacket to be a must-have. Crafted from cotton and lyocell, this jacket is lightweight and roomy, with a design that feels more comfortable through the body.

A Modern Statement: Everlane Way High-Curve Jeans

Looking for a way to keep up with the trend of tubular jeans? The Everlane Way High Curve Jean is one of the newer styles on the market, but it’s already garnering rave reviews – especially as a cosy denim piece. These cotton jeans are slightly stretchy and super soft, making them feel more comfortable after a day of wearing. But that’s not to say they’re going to get bigger and deform.

Staple Shirt: Denim Forum 80s Comfy Denim Shirt

Everyone needs a classic denim shirt in their wardrobe. In general, vintage denim shirts are best because they are already soft and comfortable to wear. Thankfully, though, Aritzia’s denim forum learned how to replicate that feeling on a new piece of clothing, and the ’80s-inspired shirt was born. It’s an oversized, loose, ultra-light transitional layering piece that you can easily wear in spring, summer, and fall/winter.

Skinny with Stretch: Good American Always Fits Good Waist Skinny Jeans

At ICYMI, skinny jeans are back – but that doesn’t mean you have to give up comfort. With this trend back in vogue, we now have the beauty of the Good American Always Fits Good Waist skinny jeans, an absolute dream for a slim silhouette. The super-stretchy, curve-hugging style fits four sizes, so think of them as the Summer of Jeans design you’ve always dreamed of.

Effortless Dress: Tuckernuck Lightweight Denim Callahan Shirt Dress

In a world where slim-fitting denim dresses are becoming increasingly popular, let us remind you of the crisp comfort that comes with the silhouette of a layered tunic outerwear. This Tuckernuck style is loved by fans for its classic colors, relaxed fit, and hidden pockets.

Strategic Silhouette: Abercrombie & Fitch High Rise Wide Leg Jean

In recent years, Abercrombie & Fitch has reinvented itself, moving away from Y2K sizing and aesthetic standards to usher in a new era of inclusivity and high-quality staples. If you haven’t visited the store since the refurbishment, you’ll be blown away by the styles and sizes here, and the comfort of these jeans is amazing. Made from cotton and lyocell, these jeans are lightweight and drape, making them feel more like a pair of comfy pajama pants than traditional jeans.

Cozy Sophistication: Good American Classic Trench Coat

Denim trench coats are a fashion trend for fall 2024. If you don’t want to be like everyone else, opt for a classic blue denim trench coat and opt for a more edgy black trench coat. This double-breasted trench coat from Good American is made from the label’s cosy stretch denim for super comfort.

All Day, Every Day: Maeve The Colette Denim High-Rise Cropped Wide-Leg Jeans

I vividly remember trying on Maeve Colette Denim’s cropped cropped cropped high-rise jeans for the first time – the comfort was unmatched. In fact, they were so comfortable that I didn’t even want to take them off. Made from cotton, lyocell and spandex, these jeans are lightweight, slightly compressed and full of stretch. Plus, the seven-minute length makes it a great choice for anyone who likes to show off their shoes.

Reimagined Sweatshirt: Pilcro Hooded Denim Popover Top

Give your hoodie a break and swap out for an edgy denim sweatshirt. The Pilcro hooded denim top is made from 100% cotton, so it’s a bit thick. That being said, it wears like a vintage denim jacket that gets softer and more comfortable with each wear. It has a unique silhouette compared to a traditional denim jacket or a Chambray shirt, and many shoppers say it has become a comfortable autumn must-have.

Drawstring Dream: Rag & Bone Ultra Featherweight Logan Wide-Leg Jean

Thanks to an innovative printing process, Rag & Bone is unrivalled when it comes to comfortable denim. Still, these comfy jeans aren’t the only cosy denim styles the brand has on offer. The Ultra Featherweight Logan wide-leg jeans are another product that stands out from the crowd, thanks to their drawstring waistband and draped Tencel denim fabric.

Kick Back in Style: New Balance 327

Is there anything more comfortable than a sturdy pair of sneakers? We don’t think there is – now, you can wear comfortable shoes while embracing the denim trend. The New Balance 327 showcases the reimagined ’70s silhouette in rich denim textures and tones, but act fast: these sneakers are sold out.

Spend Big or Go Home: Gap Mid-Rise Super-Soft Baggy Jeans

Skinny jeans may be back, but baggy jeans are still in vogue. If you want to embody your Y2K aesthetic, slip on this Gap’s cosy denim design. With a fitted waist and loose legs, these jeans look more like a pair of wide-leg sweatpants than classic jeans.

Smart Shapewear: Spanx SpanxShape EveryWear Flare Jeans

Looking for a slimmer figure? Spanx has you covered with these comfy flared jeans. The four-way stretch denim contours the abdomen, hips, hips, and legs, and feels more like your favorite medium compression leggings than a pair of stiff jeans.

Bundle Up: Brandon Blackwood Denim Logo Puffer

As the weather gets colder, few outerwear can be as comfortable and functional as a puffer coat, so try a denim-inspired puffer coat for the best of both worlds. This puffer coat from Brandon Blackwood is stamped with the logo for a streetwear look.