Plaid comes back around every fall and I always get excited, but this year we keep seeing it specifically in cute pants form. It turns out just about every retailer has a good pair of plaid pants right now…Madewell, Anthropologie, Free People, Gap, all of them. Shana mentioned the Madewell pair below as a current favorite in her fall trends article and I proceeded down the plaid pants rabbit hole from there.
The Cutest Plaid Pants We Want for Fall 2026
Fall is the most inspiring season to me, as a lover of rich autumn colors, layering, button downs, etc. I think quite a few of us are that way. And, as someone who has also forever adored menswear vibes in my wardrobe, it’s no surprise this is my favorite time of year for adding to the closet. I’m officially now on the hunt for my perfect pair of plaid pants for this year.
A few quick notes before you scroll: I tried to grab a mix here…some more office-ready pairs, some trendier vibes, some really wide-leg plaid styles, some slightly less voluminous. Stripes keep showing up as the pairing of choice this year, so you’ll see that combo a lot below. I’m in love. Let’s peruse plaid pants for fall 2026.
1 | Madewell The Devon Plaid Pants
Gahhh we love this look from Madewell…and we love that these plaid pants are pull-on = comfy. I love the slight pjs vibe without being too frumpy. The mix of stripes here with plaid is fab. To make it work, the colors have to be harmonious and I think the pants being a bit darker in tones overall helps.
2 | Maeve Avery Wide-Leg Pleated Trousers
Obviously, leave it to Anthropologie to have amazing plaid pants this year. These are so freaking cool. I’d keep it to a neutral sweater in ivory, taupe, brown up top…or throw on an oversized bomber jacket in dark brown. Denim would also work for jackets and tops here. On us shorter folks, I think a cropped/hits-at-the-waist top, sweater or jacket would work best for all that volume on the bottom.
3 | We The Free Fable Plaid Twisted Pants
The shape and seam details of these Free People pants are so cute. These just might be coming to my closet soon.
4 | Madewell The Everyday Trouser
If you want a more work-ready pair of plaid pants, these trousers from Madewell are a little more subtle and so cute. I love the striped sweater again that the model has in her hand. So fun, and a bit easier stripe-plaid combo if you’re looking for one. Offered in Short, Regular and Tall lengths.
5 | Boden Wool Blend Pleated Culottes
Ok, Boden. We love you. These are so freaking cute, and again, we have the stripes + plaid combo we’re gaga for this fall. Give me all the Jack Russell terriers + plaid + argyle + a trip to London to go with it.
6 | GAP 365 High Rise Brushed Twill Pleated Trousers
Here’s another work pant I’m excited about…and they’re a brushed fabric which should be so cozy as it cools down. The slouchy shape here is so good, but I love that they’re a true trouser shape. These will be easier to mix and match with stripes or blouses, too, with the more subtle plaid print. These also come in Regular, Tall + Petite lengths.
7 | Sanctuary Terrace High Rise Wide-Leg Pants
This pair of almost-culottes is so cute, too. I think I prefer them styled with a knee boot underneath, like on the Nordstrom model, but the other outfit is pretty cute, too. I think a tall taupe suede knee boot would be really cute with them, as well. Something like these. YES. Ooh or these.
xo,
L
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