In many of my past articles, I’ve encouraged readers to adopt a “timeless” style - a way of dressing that won’t make you cringe when you look back at your photos 10 or 20 years from now.
But recently, I had an epiphany: there’s no such thing as truly timeless fashion.
So, how should we approach our wardrobes now?
Why Timeless Fashion Doesn’t Exist
Take a step back and examine the history of men's fashion, and you’ll see that while fabrics may endure, the design, cut, and proportions of each garment evolve continuously. Even the most basic items, like jeans and t-shirts, subtly shift in fit, tailoring, and shape.
When you decide to invest in clothing, it’s often for these reasons:
Quality and craftsmanship
Distinctiveness and aesthetic appeal
The brand’s story and reputation
Simply because it looks great on you!
While an outfit can embody a timeless essence (like the classic t-shirt and jeans combo), the finer details - the cuts, proportions, and styling - inevitably shift with the times.
Looking back at the evolution of men's fashion, you'll realize that while materials may last, the design and fit of each item will never be repeated.
A perfect example is the beloved jeans. Although they've been around since the 1800s, the jeans worn by miners back then are vastly different from what we wear today, from their cut and proportions to the treatment of the denim itself.
Even your own jeans from 10-15 years ago likely bear little resemblance to the ones you wear now.
Take J.Crew’s 2011 lookbook for instance. Slim, low-rise jeans ruled the day, paired with fitted shirts and sweaters. Fast forward to J.Crew’s 2022 collection, and you’ll see high-waisted, more relaxed-fitting jeans have taken center stage. Both styles are considered "basic" staples, yet their evolution is undeniable.
Suits are another great example. Not long ago, slim-fit suits were all the rage, hugging the body closely. Nowadays, we see a shift towards more relaxed, looser fits.
While certain staple items like suits, denim, and plain t-shirts remain constants in men’s fashion, the way we wear them and the specific designs fluctuate year after year.
How to Create a Style That Stands the Test of Time?
You can avoid the pitfalls of fleeting trends by adopting a balanced mindset toward fashion. Not overly trend-driven, but not too stagnant either. It’s all about finding that sweet spot.
Opt for “Midway” Pieces
Look for items that sit comfortably between trendy and traditional: mid-rise, straight or slim straight jeans, plain white t-shirts, and classic navy blazers. These versatile choices have stood the test of time across different generations.
Wear What Feels Right for You, Right Now
Don’t stress about how your outfit will look in a few years. Focus on what makes you feel great today. Sure, this approach might seem reckless, but with time, you’ll develop a keen sense of your personal preferences - the ideal jacket length, the perfect shirt collar size, the right fit for your pants, and more.
There are plenty of ways to avoid the pressure of being out of style, especially if you keep a "neutral" mindset when it comes to choosing your outfits.
Of course, this might leave you with a few regrettable purchases along the way, but don’t just discard them - find a responsible way to repurpose or donate those items.
Smartly Mix Old and New
Blend trendy pieces with timeless staples in your wardrobe. This will help you stay current without stepping too far out of your comfort zone. It’s human nature to crave novelty, so don’t hesitate to introduce a few fresh items into your mix. This blend of the old and new will give your look both a grounded and modern edge.
At the end of the day, the concept of timelessness in fashion is a bit of a myth. But as long as your clothing choices make you feel confident and bring you joy, you’re winning the style game 😉.
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