Walk down any street in SoHo or East London lately and you’ll see it. The silhouette has changed. For over a decade, we were all trapped in the tyranny of the skinny jean, followed by the safe harbor of the "straight leg." But things are getting wider. Much wider. Bell bottoms for guys—once the punchline of 1970s disco jokes—have re-entered the chat, and they aren't just for costume parties anymore.
It’s weird, right? Most men hear "flare" and immediately think of Harry Styles at the Grammys or Mick Jagger in 1972. While those are iconic reference points, the modern reality of the flare is actually much more wearable. It’s about proportion. It’s about balance. If you’ve got broader shoulders, skinny jeans actually make you look like a lollipop. Flares? They balance that out.
The Surprising History of the Flare
People usually think bell bottoms started with the hippies. They didn't. They actually started with the U.S. Navy in the early 19th century. Back then, there wasn't a standard uniform, but sailors started wearing wide-legged trousers because they were practical. If you’re on a boat and it starts flooding, you can roll up wide pants way easier than tight ones. Plus, if you fall overboard, wide trousers are significantly easier to kick off in the water.
Fashion is funny like that. Practical naval gear became a counter-culture symbol by the 1960s. Young people started buying surplus navy pants as a "middle finger" to the establishment. By the time the 70s hit, brands like Levi’s were mass-producing the "646" and "684" models, and the flare became the dominant shape of a generation.
Then, it died. Hard.
By the 1980s, the excess of the flare was replaced by the geometric tightness of punk and the tapered "peg" of the 80s mall look. We saw a brief, somewhat tragic resurgence in the late 90s with "skater" flares and brands like JNCO, but that was more about volume than shape. What we’re seeing today is a return to the tailored, intentional flare.
Why Bell Bottoms for Guys Work in 2026
The current trend isn't just about nostalgia. It’s a reaction to the "Work From Home" era. After years of wearing sweatpants, guys realized they liked comfort, but they missed looking like they tried. A flare provides that. It’s usually fitted through the thigh—so you still get a silhouette—but then it opens up.
Think about your shoes.
👉 See also: Sport watch water resist explained: why 50 meters doesn't mean you can dive
We live in the era of the "chunky" shoe. Whether it’s Balenciaga Triple S trainers, Dr. Martens platforms, or heavy-duty Red Wing boots, skinny jeans look ridiculous with them. They create a "clown shoe" effect. Bell bottoms for guys solve this. The wider hem drapes over the bulk of the shoe, creating a long, continuous line that makes you look taller. It’s basically a cheat code for height.
The Nuance of the Cut: Flare vs. Bootcut
I see people confuse these all the time. A bootcut is the flare’s shy younger brother. It has a slight widening at the ankle to accommodate—you guessed it—a boot. A true bell bottom or flare is aggressive. The "break" starts at the knee.
If you’re just starting out, you might want to look at a "kick flare." This is a shorter, slightly cropped version that lets you show off your socks or sneakers without the fabric dragging on the ground. Nobody likes a soggy hem.
How to Wear Them Without Looking Like a Costume
This is the biggest fear. You don’t want to look like you’re headed to a Mamma Mia audition. The key is in the "top-half" styling.
- Keep the top structured. Since the bottom is wide and flowing, a baggy hoodie on top can make you look like a shapeless blob. Try a tucked-in T-shirt or a cropped leather jacket.
- Mind the rise. High-waisted flares are very "70s rockstar." If that’s not your vibe, look for a mid-rise flare that sits on your hips.
- Fabric matters. Denim is the easiest entry point. However, corduroy flares are having a massive moment because the texture adds a bit of "professor cool" to the "rockstar" shape.
Real World Examples and Brands Doing It Right
If you’re looking for where to actually buy these, the market has split into two camps: the high-end designers and the heritage denim brands.
Celine, under Hedi Slimane, basically single-handedly brought the "indie sleaze" flare back. Their "Dylan" jeans are the gold standard for that skinny-but-flared look. They’re expensive. They’re very slim. They look incredible if you have the frame for them.
On the other hand, you have brands like Wrangler. Their "Wrancher" Dress Jeans are a cult favorite. They aren't even denim; they’re a polyester twill that’s nearly indestructible. They have a permanent crease down the front, they're dirt cheap (usually under $60), and they have a perfect subtle flare. Streetwear kids and cowboys both love them. That’s a rare crossover.
✨ Don't miss: Pink White Nail Studio Secrets and Why Your Manicure Isn't Lasting
Then there’s Gucci. Under Alessandro Michele, they went full maximalist with embroidery and massive bells. While the new creative direction is shifting, those vintage-inspired Gucci flares remain a staple for anyone who wants to make a statement.
The Sustainability Factor
Interestingly, bell bottoms for guys are a huge hit in the vintage and thrifting community. Because they were so popular in the 70s and again in the late 90s, the secondary market is flooded with high-quality, "made in USA" denim that has a better shape than most modern fast-fashion versions. Searching for "Vintage Levi's 646" on eBay or Depop is often a better bet than buying something brand new that's designed to look old.
Addressing the "Manly" Question
Is it "masculine" to wear flares? It’s a question that pops up in forums a lot. Honestly, it’s a bit of a silly concern when you look at history. The most "hyper-masculine" icons of the 20th century—Robert Plant, Jimi Hendrix, even Elvis—lived in flares.
There is a certain swagger required. You can't really hide in bell bottoms. They take up space. They move when you walk. If you’re worried about looking too feminine, stick to darker washes and pair them with rugged elements like a denim trucker jacket or a heavy flannel.
Technical Details: The Hem and the Break
When you get your first pair, you have to decide on the length. This is non-negotiable.
If they are too short, they look like "high waters" and the flare effect is lost. If they are too long, you’ll destroy the heels in a week. The "sweet spot" is about half an inch off the ground while you’re wearing your preferred shoes.
- For Boots: Let the front of the hem "break" (fold) once over the top of the boot.
- For Sneakers: A cleaner, slightly higher hem is better to avoid looking sloppy.
- For Loafers: Think "70s lounge." A bit more ankle showing is fine here.
Common Misconceptions
One: "You have to be skinny to wear them."
False. In fact, if you have larger calves, bell bottoms are a godsend. They don't grip your lower leg like straight or slim jeans do. They provide room where you actually need it.
🔗 Read more: Hairstyles for women over 50 with round faces: What your stylist isn't telling you
Two: "They’re just a fad."
Every trend is a cycle. But the move away from skinny clothing is a "macro-trend," meaning it usually lasts a decade or more. We are only a few years into this wider-leg cycle. You’ve got plenty of time.
Where to go from here
If you're ready to try bell bottoms for guys, don't go out and buy the widest pair you can find immediately. Start with a "modern flare" or a "relaxed bootcut."
Look at your current footwear. If you own a pair of Chelsea boots or chunky loafers, you're already halfway there. Go to a vintage store and look for old Wranglers or Levi’s. Try them on. Walk around. Notice how the fabric moves differently than your stiff straight-legs.
Check the "Wrancher" from Wrangler if you're on a budget—they're the most "low-risk" way to test the waters. If you want to go all-in, look at Seafarer, the brand that originally made the naval bells.
Once you get used to the silhouette, you’ll probably find it hard to go back to pants that hug your ankles. There’s a freedom in the flare. It’s a bit of rebellion, a bit of history, and a lot of style. Just watch out for escalators—those hems are no joke.
Actionable Next Steps:
- Measure your inseam while wearing the shoes you plan to pair with flares; you usually need 1-2 inches more than your standard "skinny jean" length.
- Search "Vintage Wrangler Flares" on resale sites to find high-quality fabrics that hold the "bell" shape better than modern stretch denim.
- Start with a monochrome outfit (black shirt, black flares) to get used to the silhouette without the visual "noise" of high-contrast colors.