Back-to-school shopping is steeped in nostalgia for many of us, and even if we're not heading back to the classroom, the start of our own metaphorical school year inspires an impulse to ready ourselves for fall, starting with our wardrobes. This season, it's less of a checklist and more of a check-in: What piece would pull our outfits together? Do we have the right layers to bundle up? Or a sturdy boot we can wear without fail [1]? And, of course, what's the thing that we'll look forward to wearing most — you know, the kind of outfit you might save for picture day?
Our editors combed the virtual shelves, inspired by our own version of "back-to-school" shopping. Some of our "supplies" veer on the practical side — like the aforementioned boot — while other pieces are straight-up joy inducing: think whimsical sweaters and sweatshirts to pair with your favourite jeans. And if you haven't taken the season's big trends [2], like the sweater vest [3], for a spin yet, our editors have a pick for you, too.
Read on for the 19 pieces our editors are adding to their wish lists and their carts.
Ganni Two-Tone Crystal Embellished Loafers
"I thought about investing in a pair of classic black loafers from Prada or Gucci this season, but when the Ganni Two-Tone Crystal Embellished Loafers [4] ($375) arrived on my feed, I quickly changed my mind. Loafers are such a covetable shoe shape for 2021 — and I want mine to be eye-catching. These have personality and will help me jazz up my shoe closet for fall." – Sarah Wasilak, editor, Fashion
Stine Goya Adonis Knit
"I've been very into checkerboard print lately. I love the playfulness of this Stine Goya Adonis Knit [5] ($310) for fall." — Dana Avidan Cohn, executive style director
Sunday Best Winston Cropped Sweater Vest
"After months of second-guessing whether I can pull one off, I think the time has finally come to take the plunge and invest in a sweater vest. I'm eyeing the Sunday Best Winston Cropped Sweater Vest [6] ($68) in grey because I can wear the cropped silhouette on its own while it's still hot, and once the temperature starts dropping, it'll layer well over button-downs and long-sleeved tees. Catch me twinning with my future husband and the king of sweater vests, Harry Styles [7], all fall long." — Victoria Messina, editor, Trending and Viral Features
Wandler Penelope Bag
"New season, new bag. Those are words I like to live by, and my latest obsession is the Wandler Penelope Bag [8] ($775), which is a hot addition from one of my favourite brands. The colorblock look and adjustable strap makes it a versatile yet statement-making pick I can't wait to wear with everything." — Krista Jones, editor, Commerce
New Balance 550 Sneakers
"For me, back-to-school shopping always started with a pair of practical sneakers — decades later, and I'm right back where I started. I love that these New Balance 550s [9] ($185 and up) feel slightly retro but still fresh and contemporary. They're a classic that'll go with dresses, jeans, and sweats, i.e. every outfit in my fall rotation." — Hannah Weil McKinley, director, Fashion
Sunday Best Reese Bra Top and Cardigan
"I'm not quite over the cardigan and bra-top set look yet, and this cute new crop top [10] ($58) and coordinating sweater from Sunday Best [11] ($78) are giving me serious '90s back-to-school vibes. The fuzzy material is extra soft, and I just love that I can wear this set together or mix and match them separately." — KJ
Rahi Chartreuse Flora Midi Dress
"Slip dresses are still going strong, and this Rahi Chartreuse Flora Midi Dress [12] ($164) is no exception. I am absolutely in love with the silhouette of this dress, and it has quickly made its way to the top of my shopping wish list. It's the perfect piece to transition into fall, and I've already started planning all the ways I want to wear it." — Renee Rodriguez, contributing editor
Tier Window Seat Hoodie
"I met Creative Director Nigeria Ealey of Tier NYC over Zoom, and he was wearing this exact hoodie [13] ($320). When I told him I had to have it, I wasn't kidding around. The aeroplane window that looks out onto a fantasy island will have me dreaming of the summer we're saluting farewell. And right now in our world, there's no better time to dream." — SW
Agolde Pieced Angled Jean in Matrix
"Basics don't have to feel boring. Case in point: the Agolde Pieced Angled Jean in Matrix [14] ($238). These are about to shake up my whole fall look." — HWM
Pixie Market Open-Button Keyhole Top
"Cutouts keep outfits interesting, and the keyhole slits in this Pixie Market Open-Button Keyhole Top [15] ($95) make it feel anything but formal. Like an elevated version of the '90s-style cardigan trend that's been going around, this button-up is sleek and easy to pair with pants or skirts, making it another great way to get in on the cutout trend." — Chanel Vargas, assistant editor, Trending and Viral Features
Swway Cocos Sunglasses in Lavender
"If your outfit needs a little '70s-inspired je ne sais quoi, a pair of tinted sunglasses will do the trick, and this Swway Cocos Sunglasses in Lavender [16] ($65) stands out for its dramatic silhouette and colourful shades. The sunglasses also produce less water waste, fewer CO2e emissions, and 82 percent less waste overall compared to a typical pair of sunglasses, so I might have to treat myself to more than one pair." — CV
Mother Denim Drawstring Drifter Jacket
"When it's not full-on coat season yet, I find myself reaching for a great jacket — and this Mother Denim Drawstring Drifter [17] ($395) is it. It's equal parts cosy and chic, casual enough to be worn over a sweatsuit but begging to be paired with a pretty fall dress." — HWM
Precious Moments 2.0 Tank
"I've been wearing bikinis from Heavy Manners on repeat all summer, and the brand recently dropped a collection of cotton items that I'm obsessed with. This Precious Moments 2.0 Tank [18] ($65) is the perfect basic top that will pair well with absolutely everything." — RR
Ganni Rigid Denim Figni
"Ganni just launched a new batch of responsible denim that's made of 100 percent certified organic cotton, which has lower environmental impact — not to mention the perfect relaxed fit on this Ganni Rigid Denim Figni [19] ($285)." — DAC
Kate Spade New York's Winona Booties
"If wearing combat boots with a pouch for my gum is wrong, I don't want to be right. The silhouette of the Kate Spade New York Winona Booties [20] ($298) is next level, and I'm ready to rock them all through fall." — SW
Miaou Agnes Top
"I've been seeing statement corset tops pretty much everywhere I look, and I can't help but think I need one for fall. The Miaou Agnes Top [21] ($255) is at the top of my wish list. Not only does it have a flattering shape, but its fun print makes it stand out. It'd be cute with trousers and sneakers or skinnies and heels." — KJ
Re Ona Suit Trousers
"I've been all about trousers lately, and I've had my eye on these Re Ona Suit Trousers [22] ($165) for the last few months. I've been pairing my trousers with a cute corset top and Air Force 1s for the warmer days, but once it gets colder, I plan to add a cropped moto jacket to complete my look." — RR
Damson Madder Handmade Crochet Floral Scarf
"Crochet pieces have made their summer debut, and the trend is flowing right into fall with this Damson Madder Handmade Crochet Floral Scarf [23] ($41). Silk head scarves à la Olivia Rodrigo [24]'s 'Deja Vu' video have been everywhere, but this handmade crochet piece adds a cosy, personal touch to the trend. Plus, the seasonal floral design adds a subtle pop of colour that will definitely spark conversation." — CV
Thursday Boot Co. Duchess Chelsea Boots
"In preparation for long walks to pick up my pumpkin spice lattes and fall-inspired OOTD posts, I recently invested in a pair of Thursday Boot Co. Duchess Chelsea Boots [25] ($160) that complete virtually every outfit in my closet. The boots, made from sustainably sourced leather, are sleek and comfy on the soles of my feet, and they slip right on, making them a chic staple I can keep in my wardrobe rotation year-round." — CV