By Irene / MsPineappleCrafts
You've been there. You spot a gorgeous hat on a display, try it on, catch your reflection in the mirror — and immediately put it back. Something about it just feels wrong. Too big, too small, too much. You walk away thinking, "I'm just not a hat person."
But here's the truth we've learned after helping thousands of customers at MsPineappleCrafts: there's no such thing as a "bad hat face." There are only mismatched geometries. That hat you tried on wasn't wrong for you — it was wrong for the shape of your face. And that's a problem with a very simple solution.
Choosing a hat that flatters you isn't about following rigid fashion rules. It's about understanding visual balance — the relationship between the lines of your face and the silhouette of the hat. Get those proportions right, and suddenly a hat doesn't just sit on your head. It frames your entire look. This guide will show you exactly how.
Table of Content
- Finding Your Face Shape
- Your Face Shape, Your Hat — Oval · Round · Square · Heart · Oblong · Diamond
- Quick Reference Table
- Beyond Face Shape — The Fit Factor
- Caring for Your New Hat
Finding Your Face Shape
The 30-Second Gut Check
Pull your hair back, look in a mirror, and ask yourself three questions:
Is my face longer than it is wide, or about equal? Noticeably longer suggests oval or oblong. Roughly equal suggests round or square.
Where is the widest part? Cheekbones point toward diamond or oval. Equal forehead and jaw width suggests square. A wider forehead narrowing to the chin means heart.
Is my jawline sharp or soft? Angular and defined usually means square. Soft and rounded suggests round or oval.
You probably recognized yourself already. But if you want to be more precise, read on.
Want to Be Sure? The 4 Markers
Your face shape comes down to the relationship between four measurements:
- Face length — hairline to chin tip
- Forehead width — the widest point across your brow
- Cheekbone width — peak to peak across both cheekbones
- Jawline — wide and angular, softly curved, or tapered to a point
Now match your observations:
- Oval: Face length is greater than cheekbone width; forehead slightly wider than jaw
- Round: Face length and cheekbone width are nearly equal; jawline is soft with no sharp angles
- Square: All measurements are similar; jawline is sharp and wide
- Heart: Forehead is noticeably wider than jawline; chin tapers to a point
- Oblong: Face is significantly longer than wide; forehead, cheekbones, and jaw are similar widths
- Diamond: Cheekbones are the widest point; both forehead and chin are narrow
Understanding these ratios is the difference between a hat that sits on your head and one that frames your face.
Your Face Shape, Your Hat
Oval — The Balanced Canvas
You have the most flexibility of any face shape. Oval faces are gently symmetrical — slightly longer than wide, with soft proportions that don't fight against most hat silhouettes. Your biggest challenge is simply narrowing down favorites.
Berets are a natural starting point. Their soft, draped shape mirrors the balance of an oval face without adding competing angles. A classic wool beret worn slightly tilted brings effortless elegance to everything from weekend errands to evening dinners.
If you're starting a hat collection, the Wool French Beret from the MsPineappleCrafts Beret collection comes in custom sizes and a wide range of colors — the kind of hat that quietly becomes part of your daily uniform.
Round — Creating Definition
If hats have ever made your face feel fuller, you weren't imagining it — you were reaching for the wrong geometry. Round faces feature soft cheeks and a curved jawline, creating a youthful look that needs vertical structure to balance it.
The newsboy hat is your ideal match. Its paneled crown sits tall and draws the eye upward, creating a flattering vertical line that slims fullness in the cheeks. Tilted slightly to one side, it breaks up facial symmetry and adds a sophisticated edge. Avoid tight beanies and shallow caps — they emphasize roundness rather than countering it.
The Oversized Linen Newsboy Cap from the MsPineappleCrafts Newsboy Hat collection is built for exactly this — its voluminous crown creates natural lift that elongates the face while the structured brim adds definition.
Square — Softening the Geometry
Your strong jawline is striking — the right hat plays with that strength, not against it. Square faces have powerful angles: a prominent jaw, wide cheekbones, and a broad forehead. The goal isn't to hide those lines but to introduce soft curves that create contrast.
Cloche hats are your secret weapon. The bell-shaped silhouette curves gently around the face, softening the jawline while adding vintage elegance. The key is how the hat sits — low on the forehead, where the rounded brim creates a harmonious balance that highlights your cheekbones without exaggerating the jaw.
The Foldable 100% Wool Cloche Hat from the MsPineappleCrafts Cloche Hat collection is a standout — its adjustable fit hugs the head at exactly the right spot to frame a square face beautifully.
Heart — Balancing the Brow
If hats have always felt awkward on your wider forehead, you just haven't found the right brim yet. Heart-shaped faces are broader at the top, tapering to a narrower chin. The trick is choosing styles that balance that width without adding volume where you don't need it.
Medium-brim bucket hats are a fantastic match. They sit lower on the forehead, subtly narrowing the upper face while the downward slope of the brim creates a seamless visual transition from brow to chin. Berets tilted to one side and small-brim cloche hats also work beautifully by drawing attention to the eyes rather than the forehead.
The Reversible Linen Bucket Hat from the MsPineappleCrafts Bucket Hat collection offers custom sizing from S to XXL and a reversible design — two looks in one hat, both perfectly balanced for a heart-shaped face.
Oblong — Adding Width
When your face is noticeably longer than it is wide, the last thing you need is a hat that adds more height. Oblong faces benefit from horizontal presence — styles that visually widen the face and sit low on the brow rather than tall on the crown.
Wide-brim straw hats are a perfect match. The broad brim extends outward, providing a strong horizontal line that makes the face appear wider and more proportionate. They're also some of the most practical hats you can own — sun protection that works as hard as it looks. Bucket hats are another strong option, with their rounded, downward-sloping silhouette adding width while sitting low.
The Foldable Natural Straw Sun Hat from the MsPineappleCrafts Straw Hat collection has an adjustable brim you can shape wider or narrower — letting you dial in exactly the right proportions for your face.
Diamond — Framing the Cheekbones
Your cheekbones are your star feature — wide and sculpted, tapering into both a narrower forehead and chin. This is a rare and striking shape. The right hat adds gentle volume at the forehead to create a more oval visual balance, letting those cheekbones remain the focal point.
Newsboy hats are an excellent fit. The paneled crown adds fullness at the top of the head, visually widening the forehead to match your gorgeous cheekbones. Berets offer a similar effect, especially worn slightly forward. Both celebrate the angular beauty of a diamond face without making it feel top-heavy.
The Cotton Newsboy Cap from the MsPineappleCrafts Newsboy Hat collection is a bestseller that sits with just the right amount of volume — structured enough to add balance, relaxed enough to wear every day.
| Quick Reference — Face Shape Guide | ||||
|---|---|---|---|---|
| Face Shape | Best Styles | Why It Works | Caution With | Our Pick |
| Oval | Berets, newsboy hats, cloche hats, straw hats | Balanced proportions complement almost everything | Very few — most flexibility | Wool French Beret |
| Round | Newsboy hats (tall crown), structured straw hats | Adds vertical height and angular definition | Tight beanies, shallow flat caps | Oversized Linen Newsboy Cap |
| Square | Cloche hats, berets, soft bucket hats | Rounded shapes soften angular jawline | Very structured, boxy styles | Foldable Wool Cloche Hat |
| Heart | Bucket hats (medium brim), tilted berets, cloche hats | Balances wider forehead with narrower chin | Tall hats that add top volume | Reversible Linen Bucket Hat |
| Oblong | Wide-brim straw hats, bucket hats, flat berets | Adds width and visually shortens face length | Tall crowns, upright beanies | Foldable Natural Straw Sun Hat |
| Diamond | Newsboy hats, berets, wide-brim straw hats | Adds forehead volume to balance wide cheekbones | Very narrow or tight-fitting styles | Cotton Newsboy Cap |
Beyond Face Shape — The Fit Factor
Finding the right style is only half the equation. A hat can be perfect for your face shape and still feel wrong if the fit is off.
Hair volume matters. If you have thick or curly hair, you may need to size up so the hat sits at the correct level on your forehead rather than being pushed upward by your hair. This is especially true for berets and cloche hats that are designed to hug the head.
Occasion shapes the choice. A structured wool newsboy hat is perfect for a crisp autumn walk, while a soft cotton bucket hat belongs at a weekend market. Matching the hat to the moment is just as important as matching it to your face.
Hat headaches are a sizing problem. That dull, squeezing pressure across your temples after twenty minutes means the hat is too small — even half a centimeter too tight can ruin the experience. A properly sized hat should feel secure but light, like a natural extension of your outfit.
Hat hair is a sizing problem too. A hat that's too tight presses down on your hair, creating creases and flatness that linger long after you take it off. A hat that fits correctly sits lightly — it stays in place without crushing your style underneath.
The solution to both is the same: know your exact head measurement and choose a hat made to that size. MsPineappleCrafts offers custom sizing across nearly every style. If you've spent years between sizes or given up on hats fitting comfortably, the Large Size Hat collection exists specifically for you.
Caring for Your New Hat
Wool and felt hats — including berets, newsboy hats, and cloche hats — should be brushed gently with a soft-bristled brush in a counter-clockwise direction to keep the fibers smooth. Spot-clean with a damp cloth and mild soap. If a wool hat loses its shape, hold it over steam briefly and reshape by hand. Store on a hat form or stuffed with tissue.
Straw hats are more delicate than they look. Water swells natural fibers and can cause them to lose their shape permanently, so avoid soaking. Wipe down with a slightly damp cloth after wearing and store flat or crown-down. A light steaming brings a bent brim back to life.
Cotton and knit hats are the most forgiving. Most can be gently hand-washed or machine-washed on a delicate cycle. Lay flat to air dry rather than using a dryer to prevent shrinking.
Treat your hat well and it'll return the favor for years.
There's a Hat for Every Face
You walked into this guide convinced you weren't a hat person. Now you know better. The difference between a hat that makes you self-conscious and one that makes you feel unstoppable comes down to visual balance — matching the right geometry to your face.
Every face shape has its perfect match. The structured confidence of a newsboy hat, the effortless cool of a beret, the vintage glamour of a cloche, the laid-back ease of a bucket hat — one of those was made for you.
When you're ready to find yours, explore the full MsPineappleCrafts collection. Every hat is available in custom sizes, because the best hat isn't just the right style — it's the one that fits like it was made for you. Because it was.