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.
-
I'm a Senior Shopping Editor—These 25 Elevated and Rich-LookingReplica Store Fall Sale Picks Have My AttentionChic and affordable? Yes, please.
-
The New Rules of Fall Denim: No Awkward Crops, No Basic Blues, No Barrel JeansElevate your denim collection inside.
-
The Denim Trends Celebrities Are Ditching, and What They're Wearing Instead for 2025Talk about a glow-up!
-
Fashion People Just Gave Me 15 Fresh Ways to Wear Jeans Next MonthSave and style on repeat this fall.
-
Forget Flats—Everyone With Good Taste Is Wearing These Boots With Jeans and a JacketPut these on your shopping list.
-
My Mom Is in Her 50s and Asked Me for Fashion Advice—8 ChicReplica Store Outfits I Put Together for Her Under $425Outdated prints and "ugly" shoes included.
-
No, Really—This Denim Color Is Easier to Style Than Blue *and* Black JeansAnd everyone with taste is wearing it with loafers for fall.
-
From Sweden to London: The Surprising Jeans Color European Fashion People Are Reaching for This FallHere's how to pull it off.
