5 Editors on Their All-Time Favorite Fall Denim Outfits

All the Ways to Wear is a monthly series where we round up the personal twists the Who What Wear team is putting on one particular item, style, or trend. Whether it's the trending denim of the moment or the season's It print, we hope to inspire your daily outfits and up the cost per wear on some of our favorite items.

Now that I'm working from home indefinitely, there are certain items that won't be seeing the light of day too often. You know, things like high heels, silky blouses, and slip dresses, to name a few. One thing not on my don't-wear-until-life-is-normal-again list is a good pair of jeans. I've actually been wearing my favorite denim as often as ever because they strike that perfect balance of cool, casual, and comfortable. Plus, I'm just really over sweatpants. (Yes, I said it!)

I'm not the only one either. My co-workers are on the same page about jeans, especially pairs made from 100% cotton, which tend to have that slightly more vintage look and feel. Another thing we all agree on? Simple styling is the way to go this fall, and these five denim looks, in particular, will likely be worn on repeat until further notice.

Natalia Sztyk, Graphic Designer

Fall Denim Pick: Light-Wash Cropped Jeans

Classic denim outfits

Photo:

@bonatalia; STYLING: 100% cotton We The Free Dad Jeans

“This year, I have slowly transitioned my wardrobe into a more sustainable one that includes clothing only made of natural fibers, such as these 100% cotton jeans. A white T-shirt and jeans are my go-to outfit these days, and now that the weather is getting cooler, a sweater over my shoulders and suede loafers spruce up my regular go-to while still giving me the ultimate comfortability.”

Emily Gerstein, Advertising Sales Associate

Fall Denim Pick: Off-White Skinny Jeans

Neutral outfits for fall

Photo:

@eejaygee; STYLING: 100% cotton Levi's Wedgie Icon Fit Jeans

If you know me, you know I love a white winter look! I paired my new straight-leg Levi’s with a cream blazer and hoodie to create a relaxed "suit" combo perfect for when I need to feel more elevated while WFH.”

Michaela Bushkin, Senior Fashion Editor

Fall Denim Pick: Dark-Wash Straight Leg Jeans

Best dark denim

Photo:

@michaela_bee; STYLING: 100% cotton Agolde Pinch Waist High Rise Kick Jeans

"Pretty much every editor at Who What Wear raves about Agolde's Pinch Waist Jeans, so I finally decided to try them for myself. I can't get enough of the rigid fit (thanks, cotton!) and ever-so-slight flare at the bottom hem of this pair. As soon as it gets cold, I'll wear them with my favorite sneakers, a turtleneck, and an optional button-down on top."

Kia Topps, People and Talent Coordinator

Fall Denim Pick: Black High-Waisted Jeans

Best black denim

Photo:

@kiatoppss; STYLING: 100% cotton Zara Z1975 Mom Fit Jeans

I know we all technically ditched jeans for sweats during quarantine, but these jeans are my new staple for the fall. They’re comfortable; they support me in all of the right areas; and I can actually move around in them without feeling too trapped. They're so versatile I can pair them with any top, but for fall, I’ll most likely be wearing different colored cardigans every week. This one is my new favorite because it goes with a light or dark denim; it’s comfy; and it’s perfect for the puffy-sleeve phase I’m currently in.”

Natalie Cantell, Senior Director of Branded Content

Fall Denim Pick: Extra-Long High-Waisted Jeans

Denim-and-boot outfits

Photo:

@nataliecantell; STYLING: 100% cotton Zara Hi Rise Wide Leg Full Length Jeans

“When it comes to fall, the main thing my jeans need to do is look good with my go-to boots, and since lug soles are definitely a thing again, a little extra length goes a long way. I'm into high-waisted pairs and relaxed fits but cut in more structured denim—it sounds like a paradox, but I promise a stiffer cotton fabric is key to making a wider-leg look feel effortless rather than slouchy.”

Related Stories