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How to dress like a teenager at any age

How to dress like a teenager at any age

For the record, there’s no expiration date for dressing like a teenager – not at age 20, nor at 40, not even at 80. We don’t just grow out of adolescent tastes the same way we grew out of our favourite trainers. And while we may not have endless hours to perfect our keepy-ups or entire weekends to spend at the skatepark, that doesn’t mean we’ve left these affinities behind. So no need to banish any clothing from your wardrobe that indicates you still care.

We’re living in a time when style expectations are changing faster than your voice at 14, and arbitrary rules no longer carry the same weight as they did a decade ago. You can still embrace the same sensibilities you did in your coming-of-age years, and not look like you suffer from Peter Pan syndrome. But before you start digging up your old skater clothes, know that there are subtle style choices you can make to best suit your age. These are meant to serve as light guidelines and not set rules, so follow them loosely. Or ditch them altogether – your teenage self probably would.

The sportsman

Just like the final score of the big game, age is a number we tend to give too much power. A sporty sensibility is for every generation – even if you haven’t kicked a ball since your school days. Athleisure has hit the mainstream, athletic materials and details are now part of everyday dressing, and sweatpants and trainers are widely acceptable in offices. Time to get in on the action.

In your 20s

The list of interesting things happening in sportswear right now is endless, and you should lean into bolder style choices. Start by choosing pieces with statement logos, like a sweatshirt with a retro-inspired appliqué or sweatpants featuring a neon logo. Colour is another easy way to make a statement. “Have fun with it and play around with clashing combinations,” says stylist Izzy Harvey. “Sticking to true white and punctuating it with one punchy tone is another easy way to make an impact.” And don’t feel like you need to stick exclusively to sportswear brands. “Independent brands like Aimé Leon Dore, Ami, Wood Wood, and Palm Angels might now fall under the sportswear category, but they offer really cool pieces that all nod to that aesthetic in a cool, unexpected way.”

In your 30s, 40s & beyond

Instead of focussing on bold logos, Izzy encourages you to think more about textures. “Towelling is the perfect example of this,” she says. “Brands like Sunspel and Orlebar Brown produce really great options that add a bit of visual texture to your look.” Be sure to keep fit in mind as you peruse sportswear options. Styles in looser, more relaxed silhouettes will give you a cool, sporty feel, and choosing pieces in solid colours and subtle patterns will help you avoid going OTT. There are also simple details to keep an eye out for that will make this laid-back sensibility feel more mature. “A pair of drawstring trousers are a more refined take on sweatpants. They are sporty without looking scruffy.”

The skater boy

When you think of skater style, certain visual cues come to mind: Vans trainers, baggy clothes, ribbed beanies, and a skateboard that’s always within arm’s reach. This look hasn’t shed its cult appeal over the decades, which gives it a youthful edge. But one look at any skate park, and you’ll always find men in their 30s, 40s, and 50s – with distinguished salt-and-pepper hair – showing the groms how it’s done. Proof that every generation has dibs on this style.

In your 20s

“Traditionally skaters prioritise function – think robust fabrics, wide fits, and cuffed ankles – over style,” says stylist Millie Rich. “Keep the true practicalities to the pro skaters, but adopt wider fits and shapes that still capture their sensibility.” One traditional skater feature you should embrace sparingly is head-to-toe black. These are your prime years to take style risks, and bold colours and patterns, like camo, checks, and tie-dye will help you achieve that. As with sportswear, you should embrace bold, contrasting logos, as well as more eye-catching trainers, like a pair of checkered Vans.

In your 30s, 40s & beyond

Continue gravitating towards the same style elements you did in your 20s, but dial them down a notch or two. “Ditch the oversized logos,” says Millie. “You’ll find the same brands also offer designs with more discreet logos or no logos at all. These styles will immediately clean up your look.” You should also feel comfortable layering, but do so in more conservative ways. “Instead of a t-shirt over a long-sleeved shirt, throw on a button-up to smarten up your look,” she says. And complete your look with a solid-coloured trainer from Vans or Converse – classics at any age.

The mod man

The mod subculture erupted in the late 1950s and became synonymous with youthful rebellion. But unlike other subculture styles that have dwindled with time, mod is still going strong, thanks in part to its emphasis on clean, smart pieces, from Harrington jackets to crisp oxford shirts. The beauty of these pieces is that they are ageless, but there are ways of putting them together that take them from youthful to mature, or vice versa.

In your 20s

Start by taking a hallmark of mod style, like an iconic Fred Perry shirt, and pairing it with pieces that feel more youthful. Washed-out denim is a solid choice – it tones down the formality of an oxford shirt, especially if you choose a pair with distressed elements. Brogues and loafers are classic mod shoe options, but we recommend younger folks go for a pair of trainers or military boots. They feel cool, casual, and like mod fashion, they never go out of style.

In your 30s, 40s & beyond

Instead of centering your look around one mod piece, layer in multiple. “A Harrington jacket is one of those layers that translates well across all age ranges,” Millie says. “Layer yours with a polo and even a zip-up to add class and maturity.” In terms of trousers, a pair of pleated khaki chinos feels a bit more grown up then denim, but the high-waisted fit gives it a cool element that ties it back to its roots.

 


Words: Allison Pavlick
Photography: Lola & Pani
Styling: Millie Rich
Styling assistant: Isabelle Harvey