Style advice for men often falls into one of two camps: either impossibly complicated or painfully obvious. Somewhere between “buy a watch” and “wear a tailored suit” lies the real stuff, the subtle mindset shifts that make getting dressed easier, more enjoyable, and ultimately more stylish.
So we spoke to five men in their twenties and thirties about the single change that elevated the way they dress. Their answers weren’t about expensive brands or trend-chasing. Instead, they pointed to confidence, experimentation, and knowing when to let go of outdated ideas about masculinity.
“You have to let go of some masculine ideals.” — Tobi, 23
For Tobi, the breakthrough came when he stopped seeing certain style choices as “not masculine enough.”
“You have to let go of some masculine ideals. Embrace color, texture, unfamiliar silhouettes.”
Many men limit themselves to a narrow palette of black, grey, navy, and the occasional white shirt. But style gets interesting when you venture outside those comfort zones. Whether it’s a textured knit, a pair of wider trousers, or a shirt in a color you’d never normally consider, experimenting with pieces that feel unfamiliar can completely transform how you look—and how you see yourself.
“You have to be willing to experiment.” — Dimeji, 28
Style isn’t something you arrive at overnight. Dimeji believes the biggest mistake men make is expecting to get it right immediately.
“You gotta be willing to experiment a lot and not be afraid of not getting it right.”
Every well-dressed person has had outfits that missed the mark. The difference is that they kept trying. Whether it’s layering pieces differently, testing new colors, or exploring a different aesthetic altogether, experimentation is how personal style develops. The fear of looking awkward for a moment often keeps people stuck looking average forever.
“Pick an aesthetic and master it.” — Christopher, 31
With endless style inspiration online, it’s easy to become overwhelmed. Christopher’s solution is surprisingly simple.
“Pick an aesthetic and do it in different colors. Either traditional wear or linen two-pieces.”
Rather than chasing every trend, focus on a silhouette or style that works for your lifestyle and body type. If linen sets suit you, build around them. If traditional wear is your thing, explore different fabrics, cuts, and color combinations. Consistency often looks more stylish than constantly reinventing yourself.
“Lose the polo and jeans.” — Mark, 30
Mark doesn’t mince words.
“Lose the polo and jeans. You’re not 20 anymore. Play with colors, textures, and coordinating fits.”
The polo-and-jeans combination isn’t inherently bad, it just becomes a default uniform for many men long after they’ve stopped thinking about what they’re wearing. Coordinated outfits, complementary colors, and interesting fabrics communicates putting more thought into the overall look.
“Say no to tight clothes.” — Pipeoluwa, 27
For Pipeoluwa, the shift was all about fit.
“Say no to tight clothes. Looser fits, not baggy, loose. Form-fitting and free gives you relaxed, grown energy.”
For years, many men equated slim fits with style. Now, the pendulum has swung toward clothing that offers ease and movement. The key isn’t drowning in oversized garments but finding pieces that skim the body without clinging to it. The result is a look that feels more mature, effortless, and confident.
While each man approached style differently, a clear theme emerged: great dressing starts with letting go. Let go of rigid ideas about masculinity. Let go of the fear of getting it wrong. Let go of outdated uniforms and overly tight clothes.
The men who dress best aren’t necessarily the ones spending the most money. They’re often the ones willing to explore, evolve, and have a little fun with what they wear.