Up & Downs: Are Flat Bill Hats In Style In 2023?

Like a rollercoaster ride at Six Flags, the flat bill hat has seen its share of soaring highs and plummeting lows in the world of fashion.

Are flat bill hats in style? Back in the early 2000’s, flat billed caps were riding high, adorning the heads of rappers, athletes, and wannabe cool kids across America.

But with the rise of any trend comes the inevitable backlash – accusations of being “douchey” and try-hard soon had flat bill devotees shrinking.

Just as the hats curved downward, so did their popularity over the late 2000s into the next decade.

Will flat-bill hats comeback in style? Grab onto that safety bar – we’re about to find out!

The Flat Bill Renaissance

Just when it seemed flat brims were a trend well past its prime, a revival took shape on the runways and streets around 2015.

Like a phoenix rising gloriously from the ashes, the flat bill returned as part of the vintage, 90s-inspired streetwear that reigns today.

Hypebeasts and anyone longing for the days of The Fresh Prince have embraced the flat bill as the nostalgic accessory it is.

Modern looks pair it with athleisure or sporty pieces for a casual, yet put-together vibe.

To Curve or Not To Curve?


Despite its revival, the great flat bill debate wages on. Traditionally, curved brims have been seen as more formal and sophisticated.

But the flat bill oozes youthful swagger and athletic flair. For those straddling the line, a slight curve could offer the perfect sartorial compromise.

But there’s no bending the flat-out truth – once your AARP card arrives in the mail, it may be time to curve it like you’ve got some common sense.

Will Flat Bills Make a Comeback With the Youth?


Much of the flat bill’s revival can be credited to the cyclical nature of fashion.

The ’90s styles that are popular now amongst hype beasts and streetwear fans were likely what those youth were wearing the first time around.

As today’s teens reach that nostalgic age, they may similarly embrace the flat bill caps of their childhood as vintage-inspired accessories.

With its skater-slash-urban appeal, the flat bill seems unlikely to ever fade fully from counterculture fashion.

Still Douchey or Stylishly Retro?

There’s no doubt the flat bill has a divisive reputation. But as with most fashion choices, the douche factor really comes down to how you style it.

Avoid seeming like you’re trying too hard or clinging to outdated trends. Focus instead on choosing flat bills that complement your overall look.

If you can pull it off with the right retro vibes, it can elevate a casual, streetwear ensemble.

Tips for Styling Flat Bills Post-College

In your 20s, it may be tempting to rock a flat bill cap daily like it’s part of your uniform. But as you enter your 30s and beyond, you’ll want to take a more refined approach.

Here are some tips for wearing flat bills in a mature, post-college way:

Ditch the Flat Brim Baseball Caps, Choose Vintage Hats Like Flat Caps

  • Leave the overtly sporty baseball caps back in your frat house days.
  • Opt instead for vintage-inspired semi-formal hats like flat cap in corduroy, tweed, or felt – materials with more refinement.
  • A flat cap adds a subtle retro touch to a mature, polished look.

Contrast with Formal Pieces

  • Pair your flat cap with pieces like a tailored blazer, button-down collar shirt, or smart trousers.
  • The juxtaposition of the casual cap against sharp, formal clothing creates an edgy but mature vibe.
  • Try a flat cap with a leather jacket and oxford shoes for a dapper-meets-rebel aesthetic.

Skip the Stickers and Tags

  • Resist the urge to leave price tags or sticker labels on your flat cap’s brim. This screams “trying too hard.”
  • At mid-age, it’s better to keep logos and branding low-key.
  • Embrace the retro coolness of your vintage-style flat cap without the need for showy embellishments.

Final Words: The Future of the Flat Bill

While impossible to predict, the flat bill likely won’t vanish completely from the fashion scene.

However, we may see it evolve and shift from sportswear to more retro aesthetics.

As today’s hypebeasts mature, the flat bill may transition from casual hip-hop style to a nuanced throwback accessory.

One thing is certain – no matter how many twists, turns, or loops in its trajectory, the flat bill hat will continue to make heads turn.