2 hours ago
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I used to love back-to-school shopping when my children were little. The miniature highlighter pens, the name labels, those pop-out pencil cases from Smiggle, even the intergenerational wrangling over when the price of a water bottle becomes unreasonable. I love the ceremony of new beginnings. The curtain-raising drama of it all.
Luckily for me, you don’t have to grow out of back-to-school shopping even though your children do, because in fashion September is considered the start of the new year. This is eminently sensible, because this time of year is a much better moment for a restart than January. The actual new year is dark and bleak and makes resolutions and projects feel intimidating rather than exciting. But right now, the evenings are still light, and while I’ve still got a bit of a tan pretty much anything feels possible.
Back-to-school is a whole vibe, not just a shopping spree. The juice is in the back-to-school thinking, rather than the back-to-school shopping. It is about snapping back into focus, getting your head in the game. Life gets a little loose over summer, which is delicious, but sometime about now you get a restless itch for a new tempo: more coffee and less wine, more can-do and less can’t-be-bothered.
This is the most fun time of year to shop. I love seeing the swimwear and sandals swept away by crisp shirts and I-mean-business kitten heels and loafers. But this also makes it a seductive time to shop, so we need to have our wits about us.
I came across a useful protocol on stylist Allison Bornstein’s Substack, where she wrote about her fashion red flags; deal breakers that tell you that a piece isn’t going to work for you, and which you ignore at your peril. They are personal to everyone.
Bornstein’s first red flag – and I am very much with her on this – is the bra-specific top. Off-the-shoulder necklines, shoulder cut outs, open backs. These are acceptable for special occasion tops, but no one has the time to rummage for a strapless bra before work, and wardrobe-solution type bras are almost never comfortable to wear all day. Not to mention: if the person who designed the top doesn’t think about where bra straps go, it makes me wonder how much they think or care about women’s bodies – so it’s a philosophical red flag as well as a practical one.
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Green flags, meanwhile, are those items which you should snap up when you see them, because they are as rare as hen’s teeth. (Annoyingly, you will almost always spot a green flag item when taking a short-cut through M&S because you are late for a meeting, but you must try to grab them when you can.) Green flags include the perfect jeans, and an all-day bag of the right size that has a secure but unfiddly fastening and doesn’t require you to hunch one shoulder toward your ear to stay in place. I would add shoes with a 5cm-ish mini-heel that is either block-shaped or flared, so that the tip doesn’t come off when wedged in the escalator or between paving stones – you will have your personal green flags, also.
Back to the red flags. It is good to be extremely picky. Fashion has a monumental overproduction problem, so there are a lot of clothes out there. The best shoppers are utterly ruthless. One of my red flags is anything with buttons that look a bit cheap or even just boring: a bad button makes a dull coat. Another is anything that misbehaves when you move: skirts that ride up, off-the-shoulder necklines that won’t stay down. “That woman over there yanking at her top every 10 seconds looks so chic,” said literally nobody ever.
The key is to combine high standards with gritty, laser-focused realism. Do not buy a sundress you wish you’d had on your holiday last month or a grand linen ensemble perfect for a long lunch which you won’t have time for between now and 2027. Clothes should express your aspirations, but they also need to survive your Tuesdays. More than anything, back-to-school season is about clothes for real life. If a top only works with a weird bra or a bag only looks good until you put anything in it, that’s not wardrobe, that’s a fail. It goes back on the rail and you, my friend, go straight to the top of the class.
Styling: Melanie Wilkinson. Styling assistant: Charlotte Gornall. Model: Moli at Milk. Hair and make up: Sophie Higginson using Hair by Sam McKnight and Hourglass Cosmetics. Bandana, £125, Blazer, £350, and Shoes, £375, all ME+EM. Necklace, £125, Sézane. Cardigan, £49.99, Mango. Jeans, £130, Levi’s
