Most hat sizing guides tell you to wrap a tape measure around your head and check a chart. That's fine if you're buying a baseball cap. It's not fine if you're buying a beret, a newsboy cap, a cloche, or any hat where fit determines whether you look intentional or accidental.
I'm Irene, the founder of MsPineappleCrafts, and I've measured thousands of heads — some in person, most through customer messages that include a photo, a number, and a question: "Is this right?" About a third of the time, it isn't. Not because people can't use a tape measure, but because most sizing guides skip the details that actually matter.
This guide covers what they leave out: where exactly to place the tape for different hat styles, why your head shape matters as much as your circumference, how to size for children, and what to do when you fall between sizes. I'll also include a universal sizing chart you can reference for any hat purchase — not just ours.
Table of Contents
- What You'll Need
- The Basic Measurement (And Why It's Not Enough)
- Style-Specific Sizing: Berets, Newsboys, Cloches, Bucket Hats, Beanies
- Universal Hat Sizing Chart
- Head Shape: The Variable Most Guides Ignore
- What to Do When You're Between Sizes
- Measuring Children for Hats
- Common Measuring Mistakes
- How Custom Sizing Works at MsPineappleCrafts
- Frequently Asked Questions
What You'll Need
A soft, flexible measuring tape — the kind used for sewing, not construction. If you don't have one, use a non-stretchy piece of string (a shoelace works), wrap it around your head, mark where it overlaps, then lay it flat against a rigid ruler. Avoid using ribbon or elastic — they stretch and give you a smaller reading.
A mirror helps you check tape placement, but having a second person hold the tape is even better. Self-measuring tends to produce numbers that are 1–2 cm too small because you unconsciously pull the tape tighter than a hat would sit.
Measure at the end of the day. Your head is slightly larger in the afternoon and evening due to normal fluid retention. A hat that fits perfectly at 9 AM may feel tight by dinner. Measuring later gives you a more realistic fit.
The Basic Measurement (And Why It's Not Enough)
Step 1: Find your hat line
Place the tape measure around the widest part of your head — approximately 1 inch (2.5 cm) above your eyebrows in front and level with the most prominent point at the back of your skull. This is the natural "hat line" where most hats rest.
Step 2: Keep it snug, not tight
The tape should be firm enough that it doesn't slide, but loose enough that you can fit one finger between the tape and your forehead. If you can't fit a finger, you're measuring too tight. If you can fit two, you're too loose.
Step 3: Read the measurement where the tape overlaps
Note the number in both inches and centimeters. Most hat makers — including MsPineappleCrafts — use centimeters as the standard, but having both prevents conversion errors.
Step 4: Measure twice
Head shape isn't perfectly round. The tape can sit slightly differently each time, and a difference of even half a centimeter changes your size category. Measure at least twice in the same position and take the larger of the two numbers.
Your basic circumference measurement is the starting point — not the final answer. The next section explains why different hat styles need different considerations.
Style-Specific Sizing: How Fit Differs by Hat Type
This is where most sizing guides stop. They give you one number and one chart, as if every hat sits on your head the same way. They don't. A beret rests on the crown. A newsboy cap wraps the full circumference. A cloche pulls down past the ears. Each style has a different relationship with your head, and sizing adjustments matter.
Berets
Where they sit: A beret doesn't wrap around your head like a cap — it perches on top and drapes to one side. The critical measurement is the opening circumference (the inner band), which sits roughly where a headband would: across your forehead and around the back of your skull, about 2 cm above the ears.
Sizing advice: Berets should feel secure without leaving a mark on your forehead. If you're between sizes, size down for berets — a slightly snugger band keeps the beret from sliding. A too-large beret droops lifelessly instead of holding its shape.
Shop berets: Australian Wool French Beret ($32), Cotton French Beret ($22), Linen French Beret ($36). For larger heads: Australian Wool Beret for Large Heads ($32).
Newsboy Caps
Where they sit: Newsboy caps wrap the full circumference, sitting lower than berets — level with the tops of your ears or just above. The structured crown adds height, so the measurement point matters more here than for any other style.
Sizing advice: If you're between sizes, size up for newsboy caps. The structured panels don't stretch the way knit or felted hats do, and a newsboy cap that's too tight sits higher than intended, losing its signature slouch. Our handmade, custom-sized newsboy caps are built to your exact measurement — no rounding required.
Shop newsboy caps: Handmade Oversized Linen Newsboy Cap — Custom Size (from $36), Corduroy Newsboy Cap ($36), Denim Newsboy Cap ($36), Handmade Wool Newsboy Cap ($36), Genuine Leather Newsboy Cap ($45).
Cloche Hats
Where they sit: Cloches are the most fit-sensitive hat style. The bell-shaped crown pulls down over the skull to sit just above the eyebrows in front and at the nape of the neck in back — lower than any other style on this list. A cloche that doesn't fit snugly looks like a bowl; one that's too tight creates visible pressure lines.
Sizing advice: Measure slightly lower than the standard hat line — about 0.5 inches (1 cm) above your eyebrows and just above the tops of your ears. If you're between sizes, size up and use the internal band to adjust. Our cloche hats feature adjustable internal bands specifically because fit matters so much for this style.
Shop cloche hats: 100% Wool Cloche Hat ($32), Custom Felt Cloche Hat ($41), Foldable Wool Cloche ($32).
Bucket Hats
Where they sit: Bucket hats sit at the standard hat line and rely on the brim angle for coverage. The crown depth matters as much as the circumference — a bucket hat with the right circumference but too-shallow crown perches on top of your head instead of surrounding it.
Sizing advice: Measure at the standard hat line. If you want a more relaxed, streetwear-inspired fit, size up by 1 cm. If you want a secure, active-lifestyle fit, measure true to your circumference. Our Custom Linen Bucket Hat (from $36) is built to your exact measurement with the right crown depth for your size.
More bucket hats: Bucket Hat for Large Heads ($27), Linen Bucket Hat ($32), Japanese Print Reversible Bucket Hat ($27).
Beanies
Where they sit: Beanies stretch to fit, which makes sizing seem less important — until you wear a too-small beanie that creeps up your forehead every five minutes or a too-large one that bunches at the crown. Slouchy beanies need extra fabric at the crown, so their sizing is cut differently from fitted beanies.
Sizing advice: Measure at the standard hat line. For fitted beanies, choose your exact size. For slouchy beanies, the circumference should match your head exactly — the "slouch" comes from the extra height in the crown, not from a larger circumference.
Shop beanies: Cashmere Slouchy Beanie ($36), Cashmere Pom Pom Beanie ($36), Cashmere Cable Knit Beanie ($41).
Universal Hat Sizing Chart
This chart works across most hat brands, though sizing can vary by manufacturer. When in doubt, always check the specific brand's size guide.
| Size Label | Head Circumference (cm) | Head Circumference (inches) | US/UK Hat Size |
|---|---|---|---|
| XS | 52–53 cm | 20.5–20.9 in | 6½–6⅝ |
| S | 54–55 cm | 21.3–21.7 in | 6¾–6⅞ |
| M | 56–57 cm | 22.0–22.4 in | 7–7⅛ |
| L | 58–59 cm | 22.8–23.2 in | 7¼–7⅜ |
| XL | 60–61 cm | 23.6–24.0 in | 7½–7⅝ |
| XXL | 62–63 cm | 24.4–24.8 in | 7¾–7⅞ |
| XXXL | 64–65 cm | 25.2–25.6 in | 8–8⅛ |
Average women's head circumference: 55–56 cm (21.7–22 in) — Size S/M.
Average men's head circumference: 57–59 cm (22.4–23.2 in) — Size M/L.
If your measurement doesn't match a standard size exactly, see What to Do When You're Between Sizes below.
Head Shape: The Variable Most Guides Ignore
Two people with identical circumferences can need different hat sizes. Why? Because heads come in different shapes.
Oval heads are longer from front to back than they are wide from side to side. This is the most common head shape. Most hats are designed for slightly oval heads, so standard sizing usually works well.
Round heads are nearly equal in width and depth. If you have a round head, hats that are designed for oval heads may feel tight at the temples even when the circumference matches. Size up by 1 cm, or choose custom sizing.
Long/narrow heads are significantly longer front-to-back with a narrower side-to-side measurement. Standard hats may gap at the sides while feeling snug at the front and back. Custom sizing solves this entirely — at MsPineappleCrafts, we build to your circumference, which accommodates your specific shape.
How to check your head shape: Stand in front of a mirror and look at your head from above (or take a photo). If your head appears more like an egg, you're oval. If it looks circular, you're round. If it's noticeably elongated, you're long/narrow. For a deeper dive into how face and head shape affect hat choice, read our guide: How to Choose the Right Hat for Every Face Shape.
What to Do When You're Between Sizes
Falling between two standard sizes is the most common sizing frustration in hat shopping. Here's how to handle it by style:
Berets: Size down. A slightly snugger beret holds its position and shape better.
Newsboy caps: Size up. The structured panels don't have give, and a tight newsboy sits too high on the head.
Cloche hats: Size up. A too-tight cloche is visible and uncomfortable. Most cloches — including ours — have an internal adjustable band that can take up slack.
Bucket hats: Size up for casual wear, true size for a secure fit.
Beanies: Knit and cashmere beanies have natural stretch. Choose the smaller size — the fabric will conform to your head within a few wears.
Or: skip standard sizes entirely. At MsPineappleCrafts, our custom-sized hats are built to your exact measurement — 56.5 cm, 59.3 cm, 62.1 cm, whatever your tape says. No rounding, no compromising, no "hoping it fits." Enter your measurement at checkout and receive a hat made specifically for your head.
Measuring Children for Hats
Children's heads grow rapidly, and most parents underestimate how quickly a hat becomes too small. Here's a general guide by age, though individual variation is significant — always measure rather than guessing.
| Age | Average Circumference (cm) | Average Circumference (in) |
|---|---|---|
| 0–6 months | 38–44 cm | 15.0–17.3 in |
| 6–12 months | 44–46 cm | 17.3–18.1 in |
| 1–2 years | 46–48 cm | 18.1–18.9 in |
| 2–4 years | 48–50 cm | 18.9–19.7 in |
| 4–8 years | 50–52 cm | 19.7–20.5 in |
| 8–12 years | 52–54 cm | 20.5–21.3 in |
Tip for parents: When measuring children, add 1 cm to the measurement for comfort — kids won't tolerate a hat that feels even slightly tight.
For kids' hats that work for both children and petite women, see the Cotton Heart Beret for Kids ($23) and Cotton Pumpkin Beret ($23).
Common Measuring Mistakes
After reviewing thousands of customer measurements, these are the errors I see most often:
Measuring over thick hair or a ponytail. Always measure over your natural hair, but push aside any clips, buns, or ponytails. Thick braids can add 1–2 cm that won't be there when you wear the hat.
Using a metal tape measure. Construction tape measures are rigid and don't conform to the curves of your head. They consistently read 1–2 cm too large. Use a soft sewing tape or a piece of string.
Measuring too high on the forehead. If you place the tape at your hairline instead of 1 inch above your eyebrows, you'll get a smaller measurement. Most hats sit lower than you think.
Pulling the tape too tight. This is the single most common mistake. A hat doesn't compress your head — it rests on it. If the tape leaves an indentation, you're pulling too hard.
Measuring in the morning. Your head is at its smallest circumference in the morning. By late afternoon, normal fluid distribution can add 2–3 mm. Measure in the afternoon or evening for a hat that's comfortable all day.
How Custom Sizing Works at MsPineappleCrafts
Here's what happens when you order a custom-sized hat from us:
1. You measure your head using this guide and note your circumference in centimeters or inches.
2. You select your hat — any style from our collection: berets, newsboy caps, cloche hats, bucket hats, beanies, or straw hats.
3. You enter your size at checkout. On products with custom sizing, you'll see a size dropdown or a field where you enter your exact measurement.
4. We build your hat to that measurement. No rounding to the nearest standard size. Your 57.5 cm hat is a 57.5 cm hat.
5. We ship worldwide. Most orders ship within 3–7 business days, depending on the style and level of customization.
Custom sizing is especially valuable if you're at the extremes of the size spectrum — XS or XXL and beyond — where standard retail options are extremely limited. Our Bucket Hat for Large Heads ($27) and Linen Bucket Hat for Large Heads ($32) are among our most popular items for exactly this reason.
Not sure which hat style suits your face? Read How to Choose the Right Hat for Every Face Shape. Trying to decide between a beret, newsboy, or cloche? Read Newsboy vs. Beret vs. Cloche — What's the Difference?.
Frequently Asked Questions
What if I don't have a measuring tape?
Use a non-stretchy string or a shoelace. Wrap it around your head at the hat line, mark where it overlaps with a pen or pinch point, then lay it flat against a ruler. Avoid elastic, ribbon, or anything that stretches — these will underreport your measurement.
Can I measure using a hat I already own?
You can get a rough estimate by laying the hat flat and measuring the inside diameter from one side of the inner band to the other, then multiplying by 3.14 (pi). But this method is less accurate than measuring your head directly, because hats stretch and deform with wear.
My head measures 57.5 cm — should I buy a Medium (56–57) or a Large (58–59)?
For most hat styles, size up to Large. A hat that's slightly loose can be adjusted with sizing tape or an internal band; a hat that's too tight cannot be meaningfully stretched. Or, order a custom-sized hat at your exact 57.5 cm measurement — no compromises either way.
Do MsPineappleCrafts hats run large or small?
Our standard-sized hats follow the universal sizing chart above. Our custom-sized hats are built to your exact measurement. If you've had problems with hats running small from other brands, custom sizing eliminates the guesswork entirely.
How do I measure for a hat if I have long, thick hair?
Measure over your natural hair as it falls, but push aside any volumizing clips, buns, braids, or extensions. If you typically wear your hair up under a hat, measure with your hair in that position. The goal is to replicate how your head will look and feel when you're actually wearing the hat.
What if I'm buying a hat as a gift?
The best approach is to secretly measure a hat the person already owns (lay it flat, measure the inner band diameter, multiply by 3.14). If that's not possible, ask them directly — head circumference isn't something most people know, so they'll likely need to measure. As a last resort, size M (56–57 cm) fits the average adult woman, and size L (58–59 cm) fits the average adult man.
Can I stretch a hat that's too small?
Wool and felt hats can be gently stretched 1–2 cm using steam and a hat stretcher or a round object like a bowl. For details, read our complete guide: How to Stretch a Wool Hat. Straw, cotton, and linen hats cannot be meaningfully stretched — getting the right size from the start matters more for these materials.
Does head size change with age?
Yes, slightly. Most adults experience a gradual increase of about 1 cm between their 30s and 60s. If you're buying a hat you plan to keep for years, don't size down aggressively.
Have a sizing question I didn't cover? Contact us — we're happy to help you find the right fit.
Ready to shop? Browse the full collection at mspineapplecrafts.com.