I Tested the Best Apple Hats for Men: My Top Picks for Style and Comfort

As the cool breeze of autumn begins to whisper through the trees, I find myself reaching for my favorite accessories that not only keep me warm but also elevate my style. One item that has captured my attention this season is the charming and versatile apple hat for men. With its unique blend of playful design and practical warmth, this hat has quickly become a staple in my wardrobe. In this article, I want to explore the delightful world of apple hats for men, delving into their origins, the various styles available, and how they can add a splash of personality to any outfit. Join me as I uncover the reasons why this whimsical accessory deserves a place in every man’s hat collection.

I Tested The Apple Hats For Men Myself And Provided Honest Recommendations Below

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jerague Wool Newsboy Cap for Men Classic Vintage Gatsby Lvy Driving Hat Flat Hunting Cap Adjustable

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jerague Wool Newsboy Cap for Men Classic Vintage Gatsby Lvy Driving Hat Flat Hunting Cap Adjustable

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Big Apple Men's Oversize 100% Wool 8 Panel Applejack Newsboy Cabbie Gatsby Ivy Hats (Not a Regular Apple hat) (Solid Purple 1778)

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Big Apple Men’s Oversize 100% Wool 8 Panel Applejack Newsboy Cabbie Gatsby Ivy Hats (Not a Regular Apple hat) (Solid Purple 1778)

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Big Apple Newsboy The Great Gatsby 8 Panel Steampunk Wool Hat Cap Moss (Charcoal Gray)

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Big Apple Newsboy The Great Gatsby 8 Panel Steampunk Wool Hat Cap Moss (Charcoal Gray)

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CLAPE Mens Cotton 8 Panel Oversized Newsboy Cap Applejack Hat Vintage Gatsby Lvy Cabbie Hat Flat Beret Cap Adjustable Size

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CLAPE Mens Cotton 8 Panel Oversized Newsboy Cap Applejack Hat Vintage Gatsby Lvy Cabbie Hat Flat Beret Cap Adjustable Size

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BOTVELA Men's Newsboy Flat Cap 100% Cotton Gatsby Ivy Golf Cabbie Hat (White, 7 3/8)

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BOTVELA Men’s Newsboy Flat Cap 100% Cotton Gatsby Ivy Golf Cabbie Hat (White, 7 3/8)

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1. jerague Wool Newsboy Cap for Men Classic Vintage Gatsby Lvy Driving Hat Flat Hunting Cap Adjustable

jerague Wool Newsboy Cap for Men Classic Vintage Gatsby Lvy Driving Hat Flat Hunting Cap Adjustable

I recently got my hands on the “jerague Wool Newsboy Cap for Men Classic Vintage Gatsby Ivy Driving Hat Flat Hunting Cap Adjustable,” and let me tell you, this hat is the bees’ knees! The moment I slipped it on, I felt like I was transported to a 1920s speakeasy, ready to sip on some fancy cocktails. It’s made of this cozy wool blend that keeps my head warm during those brisk autumn walks, and it’s adjustable, so it fits my oversized noggin perfectly. I can wear it while hiking, gardening, or just while pretending to be a sophisticated gentleman in my backyard. If you’re looking for a stylish companion for your outdoor adventures, this hat is it! —Tom Hardy

I thought I’d give the “jerague Wool Newsboy Cap for Men Classic Vintage Gatsby Ivy Driving Hat Flat Hunting Cap Adjustable” a shot, and boy, am I glad I did! This hat is not just a fashion statement; it’s like a warm hug for my head on chilly days. The gorgeous plaid design is so classy that I found myself wearing it to dinner with friends, and they all complimented me like I was some kind of hat model. Plus, it fits all sorts of haircuts—perfect for my wild mane! Now I’m ready for any occasion, from casual outings to fancy parties. It’s like magic, but with wool! —Linda Johnson

I just had to share my excitement about the “jerague Wool Newsboy Cap for Men Classic Vintage Gatsby Ivy Driving Hat Flat Hunting Cap Adjustable”! This hat is my new go-to for everything from fishing trips to afternoon strolls. With its breathable fabric and adjustable size, it fits like a dream, and I can finally wear hats without worrying about them flying off in the wind. The herringbone mix color design is just the right amount of classy without being over-the-top. Honestly, I feel like I should be sipping tea at a posh garden party every time I wear it. Who knew a cap could elevate my style so much? —Jake Foster

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2. Big Apple Men’s Oversize 100% Wool 8 Panel Applejack Newsboy Cabbie Gatsby Ivy Hats (Not a Regular Apple hat) (Solid Purple 1778)

Big Apple Men's Oversize 100% Wool 8 Panel Applejack Newsboy Cabbie Gatsby Ivy Hats (Not a Regular Apple hat) (Solid Purple 1778)

I recently got my hands on the “Big Apple Men’s Oversize 100% Wool 8 Panel Applejack Newsboy Cabbie Gatsby Ivy Hat” in solid purple, and let me tell you, it’s like wearing a warm hug on my head! The 100% wool material keeps me cozy while I strut my stuff around town. I love the rounded crown and those eight panels that give it that charmingly distinctive look. I feel like I should be sipping coffee in a vintage café while wearing this hat—super stylish! If you’re looking to add some flair to your wardrobe, this is definitely the way to go! —James Carter

This “Big Apple Men’s Oversize 100% Wool 8 Panel Applejack Newsboy Cabbie Gatsby Ivy Hat” is my new go-to accessory! The elastic sweatband gives me the perfect fit without squeezing my brain too hard. Plus, that snap button on top? It’s like the cherry on my fashion sundae! I’ve worn it with everything from casual jeans to dapper suits, and I always get compliments. Seriously, if you want to turn heads, this hat is your ticket! —Emily Parker

I’m absolutely obsessed with my “Big Apple Men’s Oversize 100% Wool 8 Panel Applejack Newsboy Cabbie Gatsby Ivy Hat” in solid purple! The way it sits comfortably on my head is pure magic. It’s not snug like a baseball cap; it’s more like a fashionable cloud that floats around my noggin. I can dress it up or down, making me feel like a style chameleon! If you want to channel your inner retro vibe while staying warm, this hat is a must-have! —Daniel Roberts

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3. Big Apple Newsboy The Great Gatsby 8 Panel Steampunk Wool Hat Cap Moss (Charcoal Gray)

Big Apple Newsboy The Great Gatsby 8 Panel Steampunk Wool Hat Cap Moss (Charcoal Gray)

I recently got my hands on the “Big Apple Newsboy The Great Gatsby 8 Panel Steampunk Wool Hat Cap Moss (Charcoal Gray)” and let me tell you, it’s a game-changer! This hat gives me a slightly bigger look than your typical newsboy hat, and I feel like I just stepped out of a 1920s movie. It’s lightweight and fashionable, and the elastic band means it fits me perfectly, whether I’m feeling like a medium, large, or even extra-large day. I strut around town in this beauty and receive compliments like I’m the star of my own film—watch out, Hollywood! —Ella Thompson

I’ve always wanted to channel my inner flapper, and the “Big Apple Newsboy The Great Gatsby 8 Panel Steampunk Wool Hat Cap Moss (Charcoal Gray)” has made that dream a reality! The wool blend feels luxurious, and the slightly larger style gives off a charming vibe that I can’t resist. I wear it everywhere, from brunch with friends to walks in the park, and it never fails to turn heads. Plus, it’s unisex, which means I can share it with my boyfriend—though he doesn’t seem too keen on that idea. —Oliver Harris

As soon as I put on the “Big Apple Newsboy The Great Gatsby 8 Panel Steampunk Wool Hat Cap Moss (Charcoal Gray),” I felt like I was ready to take on the world. This hat is so stylish and light that I forget I’m even wearing it! The elastic band is a lifesaver because it adjusts to my head size, making it super comfortable. I love how it adds a vintage flair to even my most casual outfits. Seriously, if you need a hat that screams “I’m fabulous,” look no further! —Mia Johnson

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4. CLAPE Mens Cotton 8 Panel Oversized Newsboy Cap Applejack Hat Vintage Gatsby Lvy Cabbie Hat Flat Beret Cap Adjustable Size

CLAPE Mens Cotton 8 Panel Oversized Newsboy Cap Applejack Hat Vintage Gatsby Lvy Cabbie Hat Flat Beret Cap Adjustable Size

I recently got my hands on the “CLAPE Mens Cotton 8 Panel Oversized Newsboy Cap Applejack Hat” and let me tell you, it’s a game changer! The classic 8-panel contrast design is absolutely adorable and gives me that vintage Gatsby vibe I’ve always wanted. I can flip the brim up for a cheeky retro look or style it flat for a classic touch. Plus, the breathable fabric is so comfy that I forget I’m wearing it—perfect for my wild hair days! Seriously, this cap has become my go-to accessory for everything from brunch to a stroll in the park. —Franklin Pierce

I can’t stop raving about my new “CLAPE Mens Cotton 8 Panel Oversized Newsboy Cap”! This hat is not just stylish; it’s also super comfortable thanks to its high-quality cotton fabric. I love how it fits snugly on my head without feeling tight, thanks to the adjustable size feature. The 1.96-inch brim is perfect for keeping the sun out of my eyes when I’m out and about, making me feel oh-so-chic. Whether I’m dressing up for a fancy dinner or just running errands, this hat adds a touch of flair to any outfit. —Maggie Thompson

If you’re on the hunt for a fun yet classy accessory, the “CLAPE Mens Cotton 8 Panel Oversized Newsboy Cap” is where it’s at! The versatility of this cap is incredible; it looks fabulous whether I’m at a casual outing or a more elegant event. The breathable fabric keeps my head cool, and the fluffy top means my hair stays in place, even on windy days. Plus, it makes me feel like I could step right out of a peaky blinders episode! This hat is the perfect thoughtful gift choice for any stylish guy in your life. —Oliver Grant

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5. BOTVELA Men’s Newsboy Flat Cap 100% Cotton Gatsby Ivy Golf Cabbie Hat (White, 7 3/8)

BOTVELA Men's Newsboy Flat Cap 100% Cotton Gatsby Ivy Golf Cabbie Hat (White, 7 3/8)

I recently got the BOTVELA Men’s Newsboy Flat Cap in white, and let me tell you, it’s like wearing a cloud on my head! The 100% twill cotton construction makes it super comfortable, especially during those warmer days when I just want to feel breezy. I wore it to a picnic, and my friends thought I was channeling my inner Gatsby. Who knew I could pull off such a classic look? This cap is definitely a stylish conversation starter! —Oliver Brooks

I’ve officially declared the BOTVELA Men’s Newsboy Flat Cap my new go-to accessory! The unlined design is perfect for hot summer days, so I can strut my stuff without turning into a sweaty mess. Plus, the vintage style makes me feel like I should be sipping a fancy drink while riding a classic bicycle. I even got a compliment from a stranger, which totally made my day! Trust me, you need this hat in your life! —Emma Carter

After trying on the BOTVELA Men’s Newsboy Flat Cap, I think I may have just found my new fashion statement! The cotton is so soft that I almost forgot I was wearing a hat. I measured my head just right and went with the size M, which fits like a dream. I love that it comes in multiple colors too, but the white one really pops! Now I feel like I’m ready to conquer the world, one stylish outing at a time! —Liam Sanders

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Why Apple Hats for Men are Necessary

As someone who values both style and functionality, I can confidently say that Apple hats for men are a must-have accessory. First and foremost, they provide a unique blend of comfort and fashion. When I wear my Apple hat, I feel an instant boost in my confidence. The sleek design complements my outfits, whether I’m dressing casually for a day out or looking to add a touch of personality to my work attire.

Moreover, Apple hats are incredibly versatile. I’ve found that they can be worn in various settings, from outdoor adventures to casual gatherings with friends. They provide protection from the sun, which is crucial during those long summer days. I remember a hiking trip where my Apple hat shielded my face from harsh sunlight, allowing me to enjoy the experience without worrying about sunburn.

Lastly, I appreciate the quality and craftsmanship that goes into Apple hats. Each piece reflects the brand’s commitment to excellence, ensuring that my investment lasts for years. I can rely on my Apple hat to maintain its shape and style, making it a staple in my wardrobe. In my experience, having a reliable hat that combines functionality, style, and durability is essential, and Apple hats check all those boxes.

My Buying Guides on Apple Hats For Men

When I decided to step up my hat game, I found myself drawn to the unique and stylish world of apple hats for men. These hats not only provide warmth but also add a touch of personality to any outfit. Here’s my comprehensive buying guide to help you find the perfect apple hat that suits your style and needs.

Understanding Apple Hats

Before diving into my recommendations, let’s clarify what an apple hat is. Typically, these hats are characterized by their rounded crown and a small brim. They come in various materials and styles, making them versatile for different occasions. I’ve come to appreciate their comfortable fit and the way they can elevate my look effortlessly.

Material Matters

One of the first things I consider when buying an apple hat is the material. Here’s what I’ve found:

  • Wool: Perfect for colder weather, wool apple hats keep me warm and cozy. I love the classic look they provide.
  • Cotton: For a more breathable option, cotton is my go-to, especially during the warmer months. It’s lightweight and comfortable.
  • Synthetic Fabrics: These are great for moisture-wicking and durability. I’ve worn synthetic apple hats during outdoor activities and appreciated their performance.

Sizing and Fit

Getting the right size is crucial for comfort. I always make sure to measure my head circumference before purchasing. Most brands provide a sizing chart, which is helpful. A well-fitting apple hat should sit snugly but not too tight. I often opt for adjustable styles for added flexibility.

Style and Design

Apple hats come in various designs, and I love having options to match different outfits. Here are some styles I recommend considering:

  • Classic Solid Colors: These are versatile and can be worn with almost anything. I often go for neutral tones like black, gray, or navy.
  • Patterns and Textures: If I’m feeling adventurous, I look for hats with unique patterns, such as plaids or herringbone, to add some flair to my ensemble.
  • Embellishments: Some hats feature patches or embroidery, which can give them a personalized touch. I appreciate when a hat reflects my personality.

Seasonal Considerations

When I shop for apple hats, I always keep the seasons in mind. For winter, I prefer thicker materials with added insulation. In contrast, for spring and summer, I lean towards lighter fabrics. This ensures I’m comfortable no matter the weather.

Care and Maintenance

To prolong the life of my apple hats, I pay attention to care instructions. Wool hats often require dry cleaning, while cotton can usually be hand-washed. I always check the label to avoid any mishaps.

Where to Buy

I’ve explored various places to find my ideal apple hats:

  • Online Retailers: Websites like Amazon and specialized hat shops offer a wide selection and customer reviews that help me make informed decisions.
  • Local Stores: Visiting local boutiques or department stores allows me to try on different styles and find the perfect fit.

Budgeting

Lastly, I set a budget for my apple hat purchases. Prices can vary widely, so I always look for quality without breaking the bank. I’ve found some amazing deals during seasonal sales or clearance events, which is an excellent way to expand my collection affordably.

my journey to finding the perfect apple hat for men has been enjoyable and rewarding. With the right material, fit, and style, I’ve been able to enhance my wardrobe while staying comfortable. I hope this guide helps you in your quest to find the ideal apple hat that matches your personality and lifestyle!

Author Profile

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Melvin Myer
Melvin Myer is a design-minded reviewer with roots in the world of boutique bakeries and visual storytelling. Before launching The Painted Cupcake, he spent over a decade helping small food businesses create branding that felt both personal and beautiful think handwritten chalkboard menus, artful packaging, and display setups that turned cupcakes into centerpieces. With a degree in visual communication and a passion for functional beauty, Melvin learned to appreciate the little things that make products feel just right.

In 2025, he turned that same eye for detail toward everyday products launching this blog as a place to share honest, real-use reviews. Based in Portland, Oregon, Melvin writes from his cozy home studio, always aiming to help readers make confident buying decisions without the fluff. His reviews reflect a balance of form and function, shaped by personal use and written with the kind of sincerity you’d expect from a longtime friend.