By Irene / MsPineappleCrafts
You've seen them everywhere — on Pinterest boards, in period dramas, on the woman at the café who somehow looks effortlessly put together. The newsboy hat. The beret. The cloche. They all have that timeless, vintage energy, and from a distance they might even look interchangeable. But put them on and you'll feel the difference immediately.
Buying the wrong hat for your lifestyle is like wearing high-fashion heels on a hiking trail — it's not that the shoes aren't beautiful, it's that they don't fit the mission. The same is true for hats. Each of these three styles has its own personality, its own history, and its own way of changing how you carry yourself. Choosing between them isn't about which is "best" — it's about which one feels like you.
At MsPineappleCrafts, these three styles are our specialty. After years of crafting and fitting them, we've learned exactly what sets each one apart. Let's break it down.
In This Guide
- The Newsboy Hat — Bold Structure with a Vintage Edge
- The Beret — Effortless Cool That Goes Everywhere
- The Cloche Hat — Vintage Glamour That Frames the Face
- Side-by-Side Comparison
- How to Choose Between Them
- Styling Notes
The Newsboy Hat — Bold Structure with a Vintage Edge
What Is It?
A round, paneled crown — usually six or eight sections — stitched together and joined by a button on top, with a short, stiff brim at the front. Unlike a flat cap that sits sleek against the head, the newsboy has a "puffed" silhouette that gives it more volume and presence. You'll also hear it called a baker boy cap, gatsby cap, or applejack hat — different names for the same bold shape.
The Vibe and History
The newsboy hat was born on the streets of late 19th-century cities, worn by newspaper sellers, factory workers, and dockside laborers — men who needed a hat that stayed put during a hard day's work. By the 1920s, the style had crossed class lines entirely. It became a staple of Gatsby-era fashion, showing up on country estates and jazz clubs alike. That journey from workwear to style icon is baked into the hat's DNA, and it's why a newsboy cap still carries that effortless blend of grit and sophistication today.
Who It Flatters
Round and diamond face shapes especially. The tall, structured crown draws the eye upward, adding vertical definition that balances fuller cheeks or a narrow forehead. Tilted to one side, it breaks up symmetry and adds an editorial edge to any outfit.
When to Wear It
A fall and winter staple that pairs beautifully with heavy textures — wool coats, oversized blazers, chunky knits, denim jackets. The more structured the material, the more dressed-up it feels.
The Material Mood
What makes the newsboy endlessly interesting is how much the material changes its personality. A wool newsboy feels classic and polished — perfect for autumn walks and smart-casual layering. Switch to corduroy and the mood shifts to something warmer and more academic, like a literature professor on a weekend stroll. Denim brings streetwear energy. Leather turns it into a statement piece that anchors an entire outfit. And linen lightens everything for summer, proving this isn't just a cold-weather hat.
The Wool Newsboy Cap from the MsPineappleCrafts Newsboy Hat collection is the ideal starting point — a year-round classic in custom sizes that works with nearly any wardrobe.
Care tip: Wool newsboy hats keep their shape best when brushed gently with a soft-bristled brush in a counter-clockwise direction. Store them stuffed with tissue to hold the paneled crown — once a newsboy hat loses its structure, it loses its character.
Now, if the newsboy hat is about making a statement, the beret is about making it look like you weren't even trying.
The Beret — Effortless Cool That Goes Everywhere
What Is It?
A soft, round, flat-crowned hat with no brim and no visor. No internal structure at all — it drapes and molds to your head in whatever way you choose. Most berets feature a small "stalk" at the center top called the la queue, a remnant of the original manufacturing technique where the knitting began from a single point. That simplicity — no hardware, no brim, no rules — is exactly what makes it the most versatile hat you can own.
The Vibe and History
Few hats carry as much cultural weight as the beret. Its roots trace back to the shepherds of the Pyrenees mountains along the French-Spanish border, where the soft, flat cap was prized for its simplicity and warmth. By the early 20th century, it had migrated to the art studios of Montmartre, the jazz cafés of the Left Bank, and eventually the runways of Paris. The beret became a symbol of creative independence — worn by painters, poets, filmmakers, and revolutionaries who all shared one thing in common: they didn't follow trends, they set them.
Who It Flatters
Oval, square, and heart-shaped faces. The soft, rounded silhouette creates a gentle contrast against angular features, and the ability to tilt it — forward, backward, to the side — means you can adjust the visual balance to suit your proportions on any given day.
When to Wear It
One of the few hats that is truly year-round. A wool felt beret is a winter classic, but a lightweight cotton or linen version is a brilliant spring and summer accessory. It works just as well with a turtleneck and coat as it does with a sundress.
The Material Mood
Classic wool felt is the foundation — structured enough to hold its shape, soft enough to drape beautifully. It's the beret you picture when you think of Paris. Cotton and linen lighten things up for warmer months, giving the same silhouette a more relaxed, casual feel. And then there are the unexpected textures — a velvet beret for evening, a knit beret for weekends — each one shifting the mood without changing the essential shape.
The Wool French Beret from the MsPineappleCrafts Beret collection comes in custom sizes and over twenty colors — the kind of hat that works with everything you already own.
Care tip: Store your beret flat to maintain its shape. If it gets squished in a bag or drawer, a quick pass of steam and gentle reshaping with your hands brings it right back. Wool berets are surprisingly resilient — they want to hold their form.
Where the beret whispers, the cloche commands attention in a completely different way — through precision.
The Cloche Hat — Vintage Glamour That Frames the Face
What Is It?
A fitted, bell-shaped hat that sits close to the head with a small downturned brim. "Cloche" is French for "bell," and the moment you see one, you understand why — the smooth, curved silhouette tapers from crown to brim in one unbroken line. It's the most precise of the three hats. No tilting, no slouching, no casual draping. The cloche does one thing — frame your face with elegance — and it does it flawlessly.
The Vibe and History
The cloche is inseparable from the roaring twenties. It was designed in 1908 by French milliner Caroline Reboux, but it didn't explode until the 1920s, when the bob haircut became the defining look of the flapper era. The cloche was revolutionary because it required that short, sleek hair — it hugged the head so closely that longer styles simply didn't work underneath. It turned every woman who wore it into a silent film star. A century later, it still has that effect. Today it works with any hair length, but that spirit of polished, deliberate glamour remains.
Who It Flatters
Square and oval faces benefit most. The bell shape introduces soft, continuous curves that counterbalance a strong jawline, while the close fit complements the natural symmetry of an oval face. The low brim draws attention to the eyes and cheekbones, creating a look that's both polished and romantic. Because it sits low on the forehead, it also helps visually shorten a higher brow.
When to Wear It
The cloche is perfect for occasions where polish matters — autumn weddings, the theater, a formal brunch, a day at the races. But don't reserve it only for special events. Paired with a tailored wool coat, it instantly elevates a simple daily outfit into something special.
The Material Mood
The range is narrower than the other two — and that's by design. Wool felt is the gold standard for cloche hats because it holds the precise bell shape that defines the style. Wool blends with fleece lining add winter warmth without sacrificing the silhouette. You'll occasionally find straw cloches for summer, but the classic wool felt version is where the magic lives. The smooth surface, the clean lines, the way light falls across the curve of the brim — that's pure wool felt doing what it does best.
The Foldable 100% Wool Cloche Hat from the MsPineappleCrafts Cloche Hat collection is the bestseller — adjustable, foldable for travel, and available in custom sizes that ensure the bell sits exactly where it should.
Care tip: The cloche's beauty lives in its shape, so protect it. Never fold or crush a wool felt cloche (unless it's specifically designed as foldable). Store on a rounded form or stuffed with tissue. Keep it away from water and direct heat — both will warp wool felt permanently. A soft brush removes dust and keeps the surface smooth.
Side-by-Side Comparison
| Newsboy Hat | Beret | Cloche Hat | |
|---|---|---|---|
| Structure | Structured, paneled crown + brim | Soft, unstructured, no brim | Structured, bell-shaped + small brim |
| Vibe | Bold, editorial, confident | Artistic, effortless, versatile | Elegant, vintage, polished |
| Origin | 1890s working-class, evolved to Gatsby-era icon | Pyrenees shepherds to Parisian artists | 1920s flapper era, French millinery |
| Best face shapes | Round, diamond | Oval, square, heart | Square, oval |
| Best seasons | Fall, winter | Year-round | Fall, winter, spring |
| Occasion range | Casual to smart-casual | Casual to dressy | Smart-casual to formal |
| Styling flexibility | Moderate — tilt and angle vary the look | High — position and angle change everything | Lower — designed to sit one way, beautifully |
| Key materials | Wool, linen, denim, leather, corduroy | Wool felt, cotton, linen | Wool felt, wool blend |
| Material mood | Wool = classic; denim = street; leather = editorial | Wool = Parisian; cotton = casual; velvet = evening | Wool felt = timeless glamour |
| MsPineappleCrafts Pick | Wool Newsboy Cap | Wool French Beret | Foldable Wool Cloche Hat |
How to Choose Between Them
Forget the "rules" for a moment. The best way to decide between these three hats is to think about how you want to feel when you put one on.
Start with a beret if you want one hat that works with everything. It crosses seasons, dress codes, and moods more easily than any other style. It's the hat you grab on your way out the door without thinking — and somehow it always works. If you're building a hat collection from scratch, start here.
Start with a newsboy hat if you want people to notice. It's the most structured of the three, the most present. A newsboy hat doesn't blend in — it anchors your outfit and tells the world you chose it deliberately. If you're drawn to vintage menswear, editorial fashion, or accessories with personality, this is your hat.
Start with a cloche if elegance is your language. The cloche is the most refined of the three — it doesn't shout, but it doesn't need to. It's the hat you wear to a wedding, a gallery opening, or a Sunday brunch where you want to feel quietly stunning. If vintage glamour is your thing, the cloche is your thing.
And if you can't decide? That's not a problem — it's a wardrobe. Three hats, three moods, every occasion covered.
Styling Notes
Hair and hats: All three work with hair up or down, but each has its sweet spot. Newsboy hats look fantastic with loose waves falling beneath the brim — it softens the structure. Berets pair beautifully with a low side bun or hair worn loose and natural. Cloche hats were designed for shorter hair and still look stunning with a bob, but they work equally well with longer hair tucked or flowing.
Outfit pairing: Think of each hat as a mood board. The newsboy hat wants layers — a denim jacket, a wool coat, textured scarves. The beret lives in minimalism — clean lines, monochrome palettes, the Parisian capsule wardrobe. The cloche calls for elegance — dresses, tailored coats, vintage-inspired pieces with clean silhouettes.
The angle matters: How you position a hat changes everything. Tilting a newsboy forward adds edge. Tilting a beret to the side adds playful asymmetry. A cloche doesn't tilt — its power is in the symmetry. Knowing this means you can shift the mood of the same hat without changing your outfit.
Three Hats, Three Personalities
The newsboy hat, the beret, and the cloche might share a vintage soul, but they express it in completely different ways. One is bold. One is effortless. One is elegant. Now that you know the difference — the history, the construction, the face shapes, the materials, the mood — you'll never confuse them again. More importantly, you'll know which one was made to frame your face and your life.
When you're ready to try yours, explore all three collections at MsPineappleCrafts. Every hat is available in custom sizes — because the right style only works when the fit is perfect.