The Best Hats for Men Over 50 : Stop Dressing Like a Kid!

The Ultimate Guide to Hats for Stylish Older Men

Are you a man over 50 looking to elevate your style? It's time to embrace the power of hats! Whether you think you need one or not, hats can add a touch of sophistication and elegance to any outfit.

They’re more than just accessories; they’re essential for staying protected from the elements—whether it’s shielding you from the sun’s rays or keeping you warm in the cold.

A well-chosen hat can transform your look, boosting your confidence and style effortlessly. Ready to ditch the kid look and start dressing like the distinguished gentleman you are? Let’s dive into the best hat options for men over 50!

Why You Need a Hat (Even If You Think You Don’t)

Still not sure if you need a hat? Let’s change that! Hats are more than just fashion accessories—they have so many uses. First, a well-chosen hat can instantly make any outfit look more stylish and elegant, taking your look from plain to amazing.

But hats aren’t just about style; they’re also super practical. They protect you from the hot sun in summer and keep you warm in the winter. It’s like having your own shade or cozy cover, always ready when you need it!

And the best part? A hat that matches your style can make you feel more confident. It’s surprising how wearing the right hat can make you stand taller and feel more put-together.

So, whether you’re going to a casual hangout or a fancy event, the right hat can be your secret trick to looking and feeling your best!

Hat Style Selector

Choosing the Right Hat for Your Face Shape

When it comes to picking the perfect hat, it's important to consider your face shape. The right style can highlight your features and make you look even more stylish. For example, if you have a round face, you might want to skip hats with wide brims, as they can make your face appear fuller. On the other hand, if you have a square face, you’re in luck—you can pull off almost any hat style!

Learn more about finding the perfect hat for your face shape here.with our hat size calculator 

 

Finding the Right Hat for Your Face Shape

Round Face Shapes

If you have a round face, choosing a hat with sharp, angular designs can help balance out the roundness and add some structure to your look. Great options include the Homburg or Bowler hat, as their clean lines provide a stylish contrast.

Square Face Shapes

Good news for those with square faces—you can wear almost any hat style! To soften your features, hats with gentler lines work best. Think Fedoras or Newsboy caps; they add just the right amount of balance and flair.

Matching Your Hat to Your Style

Your hat should reflect your personal style and the kind of clothes you usually wear. If you’re into formal or classic looks, a Fedora or Homburg is perfect for adding that touch of elegance. But if you prefer a laid-back, casual vibe, a Trilby or Newsboy cap might be a better fit. The key is to choose a hat that feels right for you and complements your everyday wardrobe.

Top 6 Hats for Men Over 50

1. The Fedora

A Fedora is a timeless and versatile choice that suits a variety of occasions. With its medium brim and pinched crown, it offers a stylish look that can be easily dressed up or down. Wear it with a suit for a classic, sophisticated appearance, or pair it with jeans and a button-up for a smart-casual vibe. Whether you’re attending a formal event or just heading out for the day, the Fedora adds an effortless touch of elegance.

Perfect for: Both formal and casual occasions.

Example: 9th Street Hats 'Sinatra' Classic Fedora – a refined option that embodies the classic charm of the fedora.

2. The Trilby

The Trilby is similar to the Fedora but features a shorter brim that angles down in the front and lifts slightly at the back. This gives it a playful and modern twist, making it an excellent choice for a relaxed, summer-ready style. It’s ideal for outdoor events or casual outings when you want a touch of cool sophistication. Because of its lightweight design and stylish flair, it pairs especially well with summer outfits like linen shirts and chinos.

Perfect for: Casual settings, especially in warm weather.

Example: Men's Straw Trilby – lightweight and breathable, perfect for keeping you comfortable and stylish during those hot summer days.

3. The Panama Hat

If you’re looking for something lightweight and breathable, the Panama Hat is your go-to. Handwoven from straw, these hats are designed for warm climates, offering not only style but also practical sun protection. Available in a range of colors and styles, the Panama Hat effortlessly elevates beachwear, summer suits, or casual daywear. It’s a fantastic choice for vacations, outdoor events, or any summer occasion where you want to stay cool and look good.

Perfect for: Warm weather and summer style.

4. The Newsboy Cap

The Newsboy Cap is a relaxed and comfortable choice that works for everyday wear. Its soft, rounded shape and slightly fuller crown make it both stylish and practical, offering a snug and casual look. The beauty of the newsboy cap lies in its versatility—you can dress it up with a blazer for a smart-casual event or keep it simple with a t-shirt and jeans for an effortless, laid-back appearance.

Perfect for: Casual, everyday use or smart-casual occasions.

5. The Homburg

The Homburg is a sophisticated and formal hat, perfect for special occasions. With its stiff structure, upturned brim, and slight crease down the center, it’s often seen as a refined choice for men who appreciate classic fashion. Traditionally worn with suits or tuxedos, the Homburg gives off a polished and elegant vibe, making it ideal for weddings, formal dinners, or events where you want to stand out.

Perfect for: Formal events and special occasions.

6. The Bowler

A true icon of British style, the Bowler hat is known for its round shape and short, curled brim. Popularized during the Victorian era, it remains a stylish choice for those who appreciate classic, vintage looks. The Bowler is traditionally worn with formal attire, such as suits, and is perfect for occasions where you want to channel a sophisticated, old-school vibe. It’s a great pick for themed events, weddings, or any setting where you want to make a memorable, dapper impression.

Perfect for: Formal settings and vintage-inspired outfits.

 

 

Pro Tips for Buying the Perfect Hat

As a distinguished gentleman, you know a well-chosen hat can elevate your entire look. But finding the perfect hat—and keeping it in top shape—requires a bit of know-how. Let’s dive into expert tips for buying and maintaining your headwear, ensuring you always look your dapper best.

Try Before You Buy: The Golden Rule of Hat Shopping

The most important step when buying a hat is to try it on before purchasing. While a hat may look fantastic on the shelf, it might not suit your head. Here’s why trying it on is essential:

• Fit is Everything: A proper hat should sit comfortably, about a finger’s width above your ears and eyebrows.
• Comfort Check: Wear the hat for a few minutes. If it feels uncomfortable right away, it’s unlikely to be comfortable after hours of wear.
• Mirror Test: Use mirrors to check how the hat looks from all angles.

Pro Tip: Shopping online? Measure your head circumference carefully and compare it to the retailer’s size chart to ensure a perfect fit.

Quality Matters: Investing in Superior Materials

A well-made hat is an investment in your style. Choosing high-quality materials ensures your hat not only looks great but lasts for years:

• Felt Hats: Go for 100% wool or fur felt for durability and a good fit.
• Straw Hats: Choose tightly woven straw for better sun protection and longer wear.
• Leather Hats: Full-grain leather provides the best quality and will develop a beautiful patina over time.

Remember, investing in a high-quality hat means you’ll have a stylish piece that lasts and remains a staple in your wardrobe.

Embrace Experimentation: Finding Your Signature Style

Don’t be afraid to try something new when selecting a hat. The right style might be one you haven’t considered before:

• Try Various Styles: Fedoras, trilbys, flat caps—each offers a unique look. Experiment until you find one that feels right.
• Consider Your Wardrobe: Choose styles that match your existing outfits to create a cohesive look.
• Seek Expert Advice: Many hat shops have knowledgeable staff who can suggest flattering options based on your face shape and personal style.

Pro Tip: Take photos of yourself in different hat styles. Seeing yourself in pictures can offer a fresh perspective on which styles suit you best.

Caring for Your Hat: Maintaining Elegance

Once you’ve found your perfect hat, proper care will ensure it remains in top condition for years.

Proper Storage: Preserving Shape and Quality

Storing your hat correctly is essential to maintaining its shape and quality:

• Cool and Dry: Keep your hats in a cool, dry place to prevent mold and mildew.
• Avoid Stacking: Stacking hats can distort their shape, so store them individually.
• Use Hat Boxes: For long-term storage, invest in hat boxes to protect against dust and preserve their form.

Cleaning Techniques: Material-Specific Care

Different hat materials require different cleaning methods to keep them looking their best:

• Felt Hats: Use a soft-bristled brush to remove dust. For tougher stains, consult a professional cleaner.
• Straw Hats: Gently wipe with a damp cloth, but avoid soaking them as this can cause warping.
• Cloth Caps: Many cloth caps can be hand-washed or dry-cleaned. Always check the care label before cleaning.

Pro Tip: For sweat stains on the inner band, mix water and mild soap. Dab gently—never rub—to clean the area.

Regular Maintenance: Keeping Your Hat in Top Form

• Brush Regularly: A quick brush after each wear keeps your hat dust-free and looking sharp.
• Handle with Care: Always pick up your hat by the brim to prevent distorting the crown.
• Rotate Your Collection: If you wear hats often, rotate through your collection to give each one time to “rest” and retain its shape.

By following these expert tips for buying and caring for your hats, you’ll ensure they remain stylish, long-lasting parts of your wardrobe. Remember, a well-chosen and well-maintained hat is more than just an accessory—it’s a statement of your style and attention to detail. So go ahead, gentlemen, crown yourselves with confidence and elegance!

Where to Buy Hats for Men Over 50

Finding the right place to buy a stylish and high-quality hat is essential. Whether you’re looking for something classic or trendy, these shops offer a great selection for men over 50. Check out our top picks below:

 

Conclusion: The Crown of Your Style

Finding the right hat can truly elevate your style, adding a touch of sophistication to any outfit. Whether you’re dressing up for a special occasion or looking to enhance your everyday look, a well-chosen hat is the perfect finishing touch.

Crowning Glory: Embracing the Art of Hat Wearing

As we’ve explored the world of men’s hats, it’s clear that the right hat is more than just an accessory—it’s a statement of your unique style. Here are some key takeaways to help you master the art of hat-wearing:

• Face Shape Matters: Your face shape is the canvas, and the right hat frames your features beautifully. Whether you have a round face that suits angular designs or a square jawline that can pull off various styles, there’s a hat just waiting to complement your look.
• Personal Flair: Let your hat be an extension of your personal style. From boardroom meetings to leisurely strolls in the park, there’s a perfect hat for every occasion. The best choice is one that makes you feel confidently yourself.
• Quality Counts: Investing in a well-crafted hat pays off in style and durability. Opt for quality materials and construction, and you’ll have a stylish companion that lasts for years.
• Care with Flair: Proper storage and maintenance are crucial for keeping your hat looking sharp. A well-cared-for hat not only preserves your investment but also enhances your overall appearance.

But remember, wearing a hat transcends mere fashion trends or rules. It’s about embracing a timeless symbol of sophistication and making it uniquely yours. When you wear a well-chosen hat, you’re not just accessorizing; you’re putting on confidence, character, and charm.

So, whether you’re stepping into the hat world for the first time or you’re a seasoned aficionado, take these insights to heart. Experiment with different styles, discover what resonates with you, and wear your hat with pride. In a world where first impressions matter, why not make yours truly unforgettable?

Remember, age is just a number, but true personal style is timeless. Nothing embodies that more than a man who knows how to wear a hat. So go ahead, crown yourself with confidence. Your perfect hat awaits, ready to turn heads and spark conversations wherever you go.

Here’s to you, the modern gentleman, mastering the art of hat-wearing and making every day an opportunity to showcase your best self. Hat’s off to your style journey—or should we say, hat’s on?

 

List of Recommended Hats

• Doyle Teardrop Fedora Hat
• 9th Street Hats 'Sinatra' Classic Fedora
• Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora
• Belfry Striped Crushable Wool Trilby
• Brixton Men's Messer Medium Brim Felt Fedora Hat
• Men's Straw Trilby

1. Doyle Teardrop Fedora Hat

A sophisticated choice for the modern gentleman, the Doyle Teardrop Fedora boasts a classic teardrop crown that exudes elegance. Perfect for both casual outings and formal events.

2. 9th Street Hats 'Sinatra' Classic Fedora

Channel the timeless charm of Frank Sinatra with this classic fedora. Its versatile design makes it easy to dress up or down, ensuring you always look sharp.

3. Belfry Gangster 100% Wool Stain Resistant Crushable Dress Fedora

This stylish fedora combines durability with luxury. Made from 100% wool and stain-resistant, it's crushable for easy storage, making it ideal for the distinguished man on the go.

4. Belfry Striped Crushable Wool Trilby

A trendy twist on a classic style, this striped wool trilby is both fashionable and functional. Its crushable design ensures you can take it anywhere without worrying about shape loss.

5. Brixton Men's Messer Medium Brim Felt Fedora Hat

With its medium brim and sleek felt design, the Brixton Messer Fedora adds an air of sophistication to any outfit. It's a go-to choice for those who appreciate style and comfort.

6. Men's Straw Trilby

Perfect for sunny days, this lightweight straw trilby is your go-to summer accessory. Its casual vibe pairs well with any outfit, making it a versatile choice for relaxed outings.