The 5 Comfy Basics I'm Wearing With My Stretchiest Jeans

In the realm of pants, I’m wearing either joggers or my stretchiest jeans at the moment to keep comfortable while at home with the current situation. While I recently covered some of the coolest items to wear with sweatpants, I thought I’d focus on the latter here with a debriefing on the next-level basics I’m teaming with my go-to jeans to create cozy yet chic looks. For reference, my favorite jeans right now are from Madewell. I wear the men’s version, but I like these in general because they’re made with stretch fabric with elastane.
The simple items in question all share the same qualities—easy, versatile, and always "in” given their timeless nature. To showcase the must-haves that look A+ with jeans, I included a snap of myself and also rounded up a range of past inspirational imagery from style setters wearing the basics I’m into with those stretchy or loose jeans. Keep scrolling for a bit of outfit inspiration to wear now or note for down the road. And if you’re shopping at the moment, I also put together my favorite basics and jeans.
1. Cardigan
Cardigans of all cuts have been trending hard over the last few seasons, but it's all about those roomier, extra-soft styles worn either as tops or layered with a T-shirt that work flawlessly with stretchy jeans.
2. Comfy Tee
You can't deny the power of a jean-and-tee look. The trick is tucking in the tee for a modern vibe and choosing a T-shirt with an interesting twist like this muscle iteration.
3. Oversize Denim Jacket
One outfit idea I'm all about is my favorite stretchy black Madewell jeans with a slouchy denim jacket. I'm actually testing it out now for Zoom calls when I want to look cool up top—and I'll definitely wear this 'fit at a later date as well.
4. Relaxed Shirt
A button-down is inherently polished and pairs easily with jeans. While this ensemble features a shirt tied for a cute look, I'm into the half-tuck vibe as well.
5. Slouchy Blazer
For those Zoom meetings when I need to look professional, I like the idea of a slouchy blazer and loose jeans to look polished with comfort still top of mind.
Next, check out some work-from-home outfit ideas.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
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