Fedora, Trilby, or Porkpie? Don’t Buy a Hat Before You Read This——The Best Men’s Hat Styles for 2025
Why Hats Still Matter in Modern Men’s Fashion
Before we dive in, let me ask you a question: what’s the hallmark of a true gentleman’s outfit?
A watch, leather shoes, a bag—maybe even a pocket square if he’s wearing a suit.
But one key accessory is often overlooked: the dress hat.
When we talk about the essence of gentlemanly style, the dress hat plays a bold and elegant role. From a symbol of refinement to a staple of street fashion, hat styles have evolved with the trends.
So when a gentleman meets a hat, which style would be his favorite?
The more classic something is, the harder it is to be replaced.
As a symbol of its era, the Fedora got its name from the play Fédora, in which the heroine—Princess Fédora—appeared on stage in a soft-brimmed men’s hat with a center crease, cross-dressing in a way that sparked a fashion trend. That soft felt hat with a shallow crown became iconic, and thus, the Fedora was born.
Ever since, the Fedora has embodied a slightly androgynous elegance.
And it’s said: any man who wears a Fedora must truly understand women.
What Is a Fedora Hat?
The Fedora is the undisputed king of classic men’s hats. With its medium to wide brim, center dent, and pinched crown, it carries a timeless elegance that never goes out of style.
Key Features:
- Medium-to-wide brim
- Center crease with a pinched front
- Sloped, structured crown
Style Vibe: Sharp, sophisticated, mysterious
Best Paired With: Tailored suits, trench coats, wool coats, vintage styles
Famous Fans: Indiana Jones, Frank Sinatra, Michael Jackson
“A Fedora says you know your style—and you're not afraid to show it.”
A top quality Fedora must fulfill the following 3 points:
- Soft, Yet Strong: A true Fedora isn’t stiff — it’s flexible, with a soft, wide brim that folds easily into a briefcase when life calls you elsewhere. It’s made to move with you.
- Form Meets Function: The classic teardrop crown isn’t just for looks — it fits the shape of your head naturally, with a gentle taper that makes the hat easy to wear and just as easy to take off. Timeless style, built for today.
- Crafted, Not Assembled: Details matter. While others rely on glue, we rely on hands — skilled ones. At OTR, nearly every hat is handcrafted, from carefully chosen wool to the final stitch. Every curve, every band, every silhouette is shaped with intention — so when you wear it, it feels like it was made just for you.
Fedora: Flattering for Every Face
The Fedora is a timeless classic — and one of the most face-friendly hat styles out there. If you have a rounder face and want a little definition, you can't go wrong with a Fedora.
At OTR, our Fedora collection offers something for everyone. From classic wide-brim silhouettes to modern short-brim styles, from structured gentleman’s pieces to soft, laid-back designs — there's a Fedora for every mood and moment.
We work with a range of materials, including fine wool felt and breathable woven straw, and explore everything from rich, deep tones to playful patterns.
Whether you're going for a refined look or relaxed street style, you'll find your perfect Fedora at OTR — one that fits not just your face, but your story.
Trilby: A stylish and youthful icon of modern trends
What Is a Trilby Hat?
The Trilby is often confused with the Fedora, but look closely and you’ll spot the differences. It has a shorter brim that's angled down in front and up in back, giving it a modern, youthful flair.
Key Features:
- Narrow brim, angled sharply
- Higher crown than a Fedora
- More compact silhouette
Style Vibe: Trendy, creative, city-smart
Best Paired With: Smart-casual outfits, bomber jackets, button-downs
Famous Fans: Justin Timberlake, Bruno Mars
“The Trilby fits best in urban settings and speaks to trend-forward men.”
Porkpie: A perfect blend of vintage charm and individuality
What Is a Porkpie Hat?
The Porkpie’s signature is its flat top and round, short crown. Originally popular in the jazz era, it's a favorite among artistic types and men who aren’t afraid to stand out.
Key Features:
- Flat top with a narrow, slightly upturned brim
- Round, low crown
- Casual yet expressive look
Style Vibe: Artistic, vintage-cool, bold
Best Paired With: Relaxed outfits, linen shirts, rolled-up sleeves
Famous Fans: Buster Keaton, Walter White (Breaking Bad)
“If you like your fashion with a little rebellion, Porkpie is the way to go.”
Side-by-Side Comparison Table
| Feature | Fedora | Trilby | Porkpie |
| Brim Width | Medium to Wide | Narrow | Short |
| Crown Shape | Center-creased | Tapered/tall | Flat top |
| Formality Level | Formal to Semi | Smart-Casual | Casual/Artistic |
| Style Vibe | Elegant, Classic | Trendy, Urban | Retro, Bold |
| Best Season | Fall to Spring | Year-round | Spring/Summer |
Which Hat Style Is Right for You?
| You are... | Go for... |
| A lover of timeless style | Fedora |
| Into modern streetwear looks | Trilby |
| Expressive and artistic | Porkpie |
| New to wearing hats | Fedora or Trilby as an easy start |
| A vintage fashion enthusiast | Porkpie or Fedora |
Remember: the best hat is the one that fits your personality as well as your outfit. Try them on. Take selfies. Get compliments. Most importantly—have fun with it.
Conclusion: Crown Your Style with Confidence
Fedora, Trilby, or Porkpie—each hat tells a different story. Whether you’re stepping out in a linen blazer, denim jacket, or a three-piece suit, your hat should feel like an extension of who you are.
We hope this guide helps you better understand the different styles of men's dress hats — and makes choosing the right one a little easier.
If you have any questions or need styling tips, feel free to reach out. We're always here to help you crown your best self.
🛍️ Editor’s Picks: Explore Our Best-Selling Men’s Hats
🔹 The Westin Fedora – Classic wool felt, built to last
🔹 The Ellis Trilby – A lightweight twist on a timeless trend
🔹 The Porkpie – Vintage soul with a modern edge
🔹 Straw Fedora (Summer Edition) – Cool, breathable, and stylish in the heat
At OTRHATS, we believe in wearing your character, not just a cap. Crown your OTRA self.
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