A Grown-Up Guide to Back-to-School Shopping

There’s something Pavlovian about the heightened urge I have to check in with my wardrobe as soon as September rolls around. It might stem from the multiple core memories I have about back-to-school shopping this time of year, like placing my sock-clad foot on one of those metal contraptions at my neighborhood shoe store and watching intently as they adjusted the lever and bellowed, “A whole size bigger!” Or purchasing the same pair of J.Crew corduroy pants in multiple colors to fit the new set of hips I sprouted over the summer. Regardless, even though my body is no longer changing like it was in elementary and middle school, I can’t shake the sense of possibility that starts to percolate at the beginning of this season—that telltale impulse toward reinvention. I may not be literally growing out of my shoes anymore, but I’m still evolving, right? And my personal style is too. With that in mind, I’ve assembled what I’ll call a grown-up guide to back-to-school shopping, featuring 10 suggestions for scratching a variety of fall style itches.

The Perfect Transitional Weather Dress

Modern Citizen Debbie Sleeveless A-Line Maxi Dress $112.00

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At this point, I’ve lived long enough to guarantee that if something isn’t comfortable, I’m never going to wear it. Even if it looks amazing! I’m far too addicted to curling up on the sofa like a cat or walking long distances while listening to podcasts to sacrifice my ability to move freely. This is a very long-winded way to explain why I’m eyeing this black cotton dress from Modern Citizen. It appears both extremely comfortable and incredibly chic, thereby answering one of the questions I ask myself often, i.e., How can I look put-together but feel like I’m wearing pajamas? It’s also the kind of dress that would transition beautifully from the warmer days of early fall (paired with loafers and a light jacket) to the cooler ones ahead (I’m already daydreaming about styling it with tall black boots and an oversize crewneck sweater).

The Not-Too-Trendy Lace-Up Loafers

Paraboot Casual Lace-Up Shoes $482.00

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My very chic friend Megan O’Sullivan introduced me to Paraboots a few months ago when we were having coffee and the conversation naturally turned to the topic of loafers. She had recently bought a black pair of the brand’s classic Michael leather lace-ups, and since seeing a photo, I haven’t been able to get them out of my head. It’s technically a men’s style, but that’s only a selling point in my mind. I tend to prefer men’s loafers and sneakers. They often have cooler styles and better colors, plus the size conversion is easy: just subtract 1.5 from your standard size! I have my eye on these brown suede ones. I love how old-school they are. They’re functional, clunky, and a bit fuddy-duddy in a delightful, untrendy way. The best vibe for fall shoes, in my humble opinion, and an ideal contrast for the crisper silhouettes and textural fabrics that tend to populate my outfits this time of year.

The Ribbed Socks That Come in Every Color

Uniqlo Colorful 50 Socks $4.00

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I mourn the dissolution of cult-favorite rainbow basics brand Entireworld for many reasons but most of all because they made the BEST ribbed socks. The kind of socks that were the perfect thickness for transitioning between seasons and hit at just the right spot above your ankle and also happened to come in a variety of pleasing colors. The bad news is that it doesn’t seem like Entireworld is coming back, but the good news is that I’ve found a new go-to destination for this style of sock: Uniqlo, baby! The style is actually called “Colorful 50 Socks,” which I commend for its straightforwardness. I have five pairs in my shopping cart right now, and just in case you’re nosy like me, the colors I’ve chosen are 12 Pink, 44 Yellow, 57 Olive, 69 Navy, and 16 Red. I’d be honored if you copied this selection exactly (possibly offended if you don't).

The Classic Navy Sweater That’s 100% Cotton

L.L. Bean Men’s Organic Cotton Rollneck Crew Sweater $70.00

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Since I’ve already disclosed that I am a delicate flower who prioritizes comfort above all else, it probably won’t surprise you to learn that I can get absolutely giddy over a good cotton sweater. I vastly prefer cotton to wool or even cashmere, regardless of the weather, because it doesn’t itch my arms, but the thing is, cotton sweaters are kind of rare—especially for anyone who isn’t a 2-year-old—so my antennae are always on high alert whenever I’m browsing online. Over the years, I’ve found L.L. Bean to be a reliable resource, and right now I’m particularly interested in this 100% cotton roll-neck sweater (in navy, to be precise). If I were to buy it, which is likely, I’d get it in a size that’s either slightly too small or slightly too big. I’m the opposite of Goldilocks when it comes to sweaters. “Just right” doesn’t do it for me. I want it to either fit snugly in a way that’s conducive to tucking into high-waist pants (almost like a thick long-sleeve shirt) or swallow me whole like a blanket with arm holes.

The Traffic-Cone Orange Scarf to Spice Up Your Autumnal Neutrals

HimalayanEShop Cashmere Knitted Shawl $59.00

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I wear a lot of color in the summer—like a lot—so by the time fall rolls around, I’m definitely in the mood to reacquaint myself with browns and blacks and creams and charcoals. Dressing in head-to-toe neutrals can get boring fast, though, which is why I think it’s useful to have a few eye-popping accessories in your autumnal assortment, such as an enormous traffic-cone orange scarf. Why orange? There’s something about it that feels more complementary to neutral colors than other options. Yellow would be good too though.

The Sleeper Hit Purple (Yes, Purple!) Pants

COS Wide-Leg Linen Pants $99.00

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I’m about to contradict everything I just said about craving neutrals and advocate for getting a pair of eggplant-colored pants because having at least one pair of pants in a slightly bizarre color or pattern can be a sleeper hit outfit–generating hack. Mainly in the sense that a pair of pants in a slightly bizarre color of pattern can “make” an entire outfit without much additional effort. I also just happen to love these purple pants from COS so much. They’re the perfect shade of purple. They’re dark enough that they still feel subtle and sophisticated but punchy enough to transform a plain white T-shirt and black blazer into a bonafide LOOK, and that’s powerful.

The Velvet Slippers You Can Wear Outside Your House

Le Orsine Volterra Slippers $137.00

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I’m a huge fan of Le Orsine, a Milan-based brand that makes velvet shoes using an age-old technique from northeastern Italy. Each pair of shoes is one-of-a-kind and handcrafted by local artisans with recycled materials (for example, the soles are made from old bicycle tires!). I already have a navy pair with brown trim that I wear incessantly. They’re perfect for outfits in need of flat shoes that aren’t as feminine as ballet flats or as classic as loafers. I love to style them with tea-length kaftans in warmer weather and with trousers and a striped sweater when it’s cooler. If I were to buy a second pair, I would go for either the classic slippers in burgundy with pink trim or a pair of green or yellow Mary-Janes.

The Go-With-Everything Brown Belt

Lands’ End Men's Leather Braid Belt $45.00

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Historically I’ve never been a "belt person", so it doesn’t often occur to me to incorporate them into my outfits. On the sporadic occasion when it does, I borrow one of my husband’s because I don’t actually own one myself. Lately, though, I am a changed woman—at least where belts are concerned. They’ve been playing a starring role in many of my recent fall outfit fantasies to the point where I am now considering buying this braided brown leather style from Lands’ End. (If you’re wondering whether one of my outfit fantasies involves belting the aforementioned purple pants with the navy cotton sweater tucked in on top and perhaps the suede Paraboots on my feet and an olive green jacket over my shoulders, then I would say we’re surfing the same wavelength).

The Secondhand Sequin Bag Splurge

The RealReal Various Styles $40.00

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As we enter the season of heavier and warmer functional fabrics, I rely on bags to inject a dose of impractical, unserious contrast. Something sequined often does the trick, as does something bright and satiny. The RealReal is my favorite place to look for this type of thing, and right now my “favorites” section features this cute little Prada mini, this ambassador for highlighter pink, and this Bottega clutch. Please note that not a single one of these bags is big enough to accommodate a binder or a textbook, which is how you know this really is a back-to-school shopping guide for grown-ups—just like I promised.