As fashion editors, it’s our job to bring you, dear readers, a digest of what matters in fashion. This includes everything from the latest shopping picks to the most interesting trends to the chicest outfit ideas worth testing out. Today, we thought we’d focus specifically on the latter here. Given that we’re consistently scrolling through IG and various street style imagery for outfit inspiration, our saved folders are full of top-notch ‘fits. Many of said looks appear across our various stories (you may enjoy this piece on fall dress outfits or this one on comfy looks). But while there are many recent outfit formulas that have piqued our interest over the last few months, there are a few specific outfits that are front-runners in our eyes. Essentially, it’s these looks that we think define the entire season.
Here, we’re talking about directional ensembles featuring many relaxed and simple pieces that bring comfort and ease to a vibe—ideal for dressing during these current times. Keep scrolling to check out the outfits that define fall 2020. You’ll also find a smattering of shopping inspiration as well. Go on, you may just uncover a fresh ‘fit that could just become one of your new go-to looks.
“The shacket has been bubbling for a while now, but I feel like this fall, it has reached peak trend. With a lot of us hatching plans for the perfect outdoors escape, the outerwear feels low-key, but also stylish. I like that it does most of the styling work for you—simply put on any neutral basics underneath and a pair of trusty boots. This extra-long one from H&M could also be worn as a dress in a pinch.”—Kat Collings, editor in chief
“I think we can all agree that the #1 outfit goal this season is making sweatpants look a little chicer. The no-brainer way to do so is to throw on an oversize blazer, whether you’re venturing out or making a Zoom appearance. And it wouldn’t be 2020 without a face mask and New Balance sneakers.”—Allyson Payer, senior editor
“The ’90s-inspired leather jacket trend continues to reign supreme this fall. The oversize shape lends a forward feel to even the simplest outfits, but right now, fashion girls are particularly fond of styling the jackets with their knee-high boots and shorter hemlines to create that ‘bare legs’ look that’s everywhere.”—Anna LaPlaca, associate editor
“There’s nothing that defines fall 2020 quite like the sweater-vest. The grandma trend has flooded our feeds this season—spotted on all our favorite influencers. Whether you opt for a cool print or a neutral hue it will add a preppy-cool look to all your fall ensembles. I’m particularly partial to a slightly oversize fit styled over a button-down or collared blouse.”—Judith Jones, market editor
“This fall, I am all about the big-blazer–and–big-wellies look. Whether you dress it down with a sweatshirt and comfy shorts or jazz it up with a sleek mini dress and printed shoulder bag. I love how forward the chunky boots look against the tailored blazer. As I said, I’m all about it.”—Lauren Eggertsen, senior fashion editor
“This is my pick. It’s all about classic pieces with a twist. This specific outfit feels modern yet timeless. The slouchy white-shirt–and–straight-leg-jeans combo is A+ on its own (perfect for Zoom meetings), and the addition of the sweater tied around takes the look to the next level.”
