Hats can completely transform your look. The right hat acts as the cherry on top, adding personality and flair to any outfit.

But with so many styles to choose from, it can be tricky to find your perfect match.

Here we walk you through the key types of men’s hats, when and how to wear them, and tips for picking the best hats for you.

The Dapper Fedora

The fedora is a timeless classic that always brings an extra dash of retro cool. Its clean lines and structured silhouette add vintage appeal to both formal and casual looks.

You’ll make quite the entrance by pairing a fedora with a sharp suit or blazer for weddings, dates, and formal events. But a fedora can also lend a touch of sophistication to everyday outfits like jeans, sweaters, and leather jackets.

When shopping for a fedora, look for high-quality materials like wool felt or suede. Then choose a versatile neutral color like tan, gray, or black. The possibilities are endless when you find the right fedora to complement your personal style.

The Rugged Flat Cap

Beloved by countryside gents and hip urbanites alike, the flat cap brings a bit of rugged flair reminiscent of the past. It’s an endlessly versatile hat that works for dressy and casual occasions.

Flat caps pair perfectly with button-downs, polos, crewneck sweatshirts, and tees. For a more refined look, wear one with a sport coat or tailored blazer. And a leather flat cap adds a sleek touch of edge to any outfit.

To find your match, look for flat caps in materials like tweed, corduroy, and wool. You can find some great flat caps over at Gaelsong. Whether you opt for a traditional herringbone wool or modern solid-color cap, you’ll add instant personality.

The Breezy Panama Hat

When the weather heats up, beat the sun in style with the ultimate warm weather hat: the Panama. The Panama hat wicks away sweat and provides superior sun protection, all while lending a dash of sophistication.

For tropical vacations and steamy summer days, a Panama hat perfectly complements linen suits, breezy button-downs, and polos. The breathable straw construction and ventilated design will keep you cool and comfortable whether you’re sightseeing or sipping cocktails by the beach.

Look for a Panama made from genuine Ecuadorian toquilla straw for the best quality. Then shape the brim and crown to flatter your face. This hat is built to last for years of stylish shade.

The Cozy Beanie

As soon as autumn hits, reach for a beanie to keep your head warm without sacrificing an ounce of style. This winter essential adds a casual touch of flair to any cold weather outfit.

For grabbing coffee, walking the dog, and running errands, pair your beanie with a jean jacket, sweater, and sneakers. Or layer it with a wool overcoat and scarf for extra warmth on the way to the office.

Choose a tight-knit wool or cashmere beanie in a neutral color like black, gray, or navy for an effortlessly cool look. With the right beanie, you’ll stay toasty all season long.

The Dashing Trilby

Somewhere between a fedora and a flat cap lies the trilby. With its short brim and indented crown, the trilby provides an instant dose of retro charm. It’s the perfect hat for gents looking to stand out with sophisticated flair.

The trilby transforms basic button-downs and blazers into head-turning looks. And it adds polish and personality when paired with crisp suits. For a modern edge, style yours with dark denim and leather boots.

Look for trilbys in materials like wool felt, tweed, and cotton.

The Casual Baseball Cap

Nothing beats the carefree cool of a baseball cap on weekends and days off. It’s the ideal hat for running errands and enjoying the outdoors.

Baseball caps complement athletic outfits, tees, tanks, and hoodies effortlessly. Keep it casual with a pair of joggers or embrace the sporty vibe with shorts. Just avoid overly formal looks.

Focus on fit and comfort when choosing a baseball cap. Curved brims and adjustable straps ensure the cap hugs your head perfectly. Then pick a design that speaks to your interests, whether it’s a favorite team logo or an eye-catching graphic.