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Revised 3/16/26
For every guy who just needs a hat that works
Men's Hat Buying Guide
Whether you found this guide because something changed, or you just want a dependable hat you'll actually wear, you're in the right place.
Most men don't plan to spend time reading about hats.
But something changed, or is changing, and now it matters in a way it didn't before. Maybe it's practical: you need coverage and you're not sure what to buy. Maybe you've been carrying something harder than that for longer than you've let on to anyone, and you just want to look like yourself again. Either way, you're in the right place.
We've been helping men find the right hat since 1995: bald guys, guys in treatment, guys who just want something that finally works. This guide covers everything you need to get there. And if you need more than a hat, we have that too.
Here because of hair loss, alopecia, or chemotherapy? Your section is waiting.
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Step 1: Get Your Size Right
Where to start
A hat that's too tight becomes uncomfortable within the hour. One that's too loose shifts around and never looks right. Sizing takes two minutes and makes everything else easier.
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How to measure your head for a hat. Wrap a soft measuring tape around your head, just above your ears, across the middle of your forehead, and around the fullest part of the back of your head. That number is your head circumference. Match it to the chart below.
| Size | Head Circumference | CM | Traditional Hat Size |
|---|---|---|---|
| Small | 21 1/8 – 21 1/2" | 54–55 | 6 3/4 – 6 7/8 |
| Medium | 21 7/8 – 22 1/4" | 56–57 | 7 – 7 1/8 |
| Large | 22 5/8 – 23" | 58–59 | 7 1/4 – 7 3/8 |
| XL | 23 1/2 – 23 7/8" | 60–61 | 7 1/2 – 7 5/8 |
Between sizes? Go up. You can fine-tune a slightly large hat with hat sizing tape or a terry cloth sweatband reducer. You can't do much with one that's too small.
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How should a hat fit?
A good hat should feel secure but never tight. It should sit comfortably just above your ears, stay in place when you move, and not leave deep pressure marks on your forehead. If it slides around easily it may be too large. If it feels tight after a few minutes it may be too small. A useful test: you should be able to fit one finger between the band and your head.
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Step 2: Choose Your Style
Start with how you plan to wear it
Everyday Caps
Baseball caps, driver caps, flat caps, and newsboy caps. Low profile, easy to wear, versatile enough for almost anything. The most popular category for daily wear.
Seasonal note. Same silhouette year-round; what changes is the fabric. Cotton and linen for spring and summer, wool and tweed for fall and winter. Driver and flat caps work especially well for men who want something that looks intentional without trying too hard.
Adventure & Classic Hats
Outback hats, adventure hats, casual fedoras. More presence than a cap, but not formal. Good for travel, outdoor errands, and anywhere you want a little more personality.
Travel pick. The Mens Wool Felt Packable Fedora is specifically designed to be packed and reshaped without damage. Many outback and felt styles also come in wool for fall and winter wear.
Sun & Outdoor Hats
Bucket hats, safari hats, boonie hats, and fishing hats. Built for full coverage: a brim that wraps all the way around to shade your face, ears, and neck. Most carry a UPF 50+ rating.
What does UPF 50+ mean?
UPF stands for Ultraviolet Protection Factor. It means the fabric itself blocks UV rays, not just provides shade. A UPF 50+ hat blocks over 98% of UV radiation. Worth paying attention to for anyone spending real time outside, whether or not you have hair loss.
Match the hat to the activity. A cotton bucket hat is great for the beach. A supplex safari with mesh panels is built for serious heat. A long brim fishing hat with a neck flap is designed for a full day on the water. Most fold flat for travel.
Cold Weather Hats
Fleece-lined knit cuff caps, insulated winter beanies, and wool and tweed styles. When warmth is the job, these do it well, without bulk.
Layering tip. Several styles are slim enough to fit under a hood. Look for cuffed beanies and fleece-lined knit caps if that matters to you.
Beanies & Sleep Caps
Soft, close-fitting, no brim. Our most popular men's category. Cotton and bamboo beanies for everyday wear, fleece for warmth, and dedicated sleep caps for overnight use, including CPAP-compatible styles.
Sleep caps are a different product. Our organic cotton sleep cap has an adjustable cuff, flat interior seams, and is CPAP-friendly. The fleece version adds warmth for colder months. Customers come back for these year after year.
Using a CPAP machine? A hat worn under your mask straps cushions the skin, prevents strap marks, and keeps your head warm without interfering with airflow. Look for soft, close-fitting styles with flat interior seams and no bulk near the mask. Our organic cotton sleep cap is specifically designed for CPAP compatibility. See our full guide to CPAP hats →
Choosing for your face shape. Round face: structured caps and medium brim styles add definition. Oval face: most styles work well. Square face: driver caps and flat caps balance a strong jawline. Long face: wider brims worn slightly lower add width and balance proportions. These are starting points, not rules. If a hat feels right on you, that's the right answer.
Hats for Bald Men and Hair Loss
What bald guys actually want to know
You probably didn't plan to read a hat guide today.
Something brought you here. Maybe your hair has reached a point you can't quite ignore anymore. Maybe you just started treatment and someone mentioned you'd want a hat. Maybe you've been getting by with the same cap for a couple of years and you've finally decided to actually deal with this. However you got here, we're glad you're here.
Hair loss changes things. It changes how you get ready in the morning. It changes whether you want to be in photos. It changes the version of yourself you see in the mirror. Men don't talk about this much. They joke about it instead, and most of them have been making those jokes for longer than they'd admit. What we hear, again and again, is that most of them have been carrying this longer, and harder, than the people around them realize.
The feeling is real, and it's worth saying plainly: losing your hair is hard. Not the end of the world, but genuinely hard. Especially if it came early, or fast, or because of something you didn't choose. Two thirds of men experience noticeable hair loss by 35. Most of them never say a word about how it actually feels.
We know that. We've been having this conversation with men for 30 years.
The thing about hats
A hat doesn't fix the feeling. But it can give something back.
What men who've been through this describe isn't just coverage. It's a shift. A hat stops being something you're hiding behind and starts being part of who you are. The driver cap that becomes your thing. The baseball cap you grab every morning without thinking. You stop tracking what's underneath it and start thinking about how you look overall. You stop looking at reflections the same way. That shift is quiet and real and it matters more than any style guide will tell you.
There are hundreds of thousands of men in online communities built specifically around navigating hair loss. That's how many men are quietly carrying this. You are not alone in it, and you are not unusual for caring about it.
Wanting to look good right now is not shallow.
Caring about this doesn't make you vain.
The practical guidance is below when you're ready.
If You're Going Through Chemotherapy
The stakes feel different when treatment is the reason. This isn't about vanity. It's about walking into a room and feeling like yourself rather than like a patient. It's about your kids not seeing worry on your face when you come downstairs. It's about having one small part of your appearance that you control on a day when so much feels out of your hands.
We've been sitting with that reality for 30 years. Our team is always available if you want to talk through what you need. You don't have to figure this out alone.
If you're also dealing with eyebrow loss, we carry men's eyebrow solutions, something most people don't think to mention until it matters. And if a hat isn't the only option you want to explore, we also carry men's wigs and hairpieces.
Will a hat draw more attention to my hair loss?
This question applies whether you're dealing with pattern baldness, alopecia, or hair loss from chemotherapy, and it deserves a straight answer.
Almost never. A hat that fits well and looks like yours reads as exactly that: a hat. It doesn't announce what's underneath. What actually reads as self-conscious isn't the hat. It's the adjusting, the deflecting, the checking. The hat is fine. The anxiety around the hat is what people pick up on, and that tends to settle once you find the right one and stop second-guessing it.
Men who've gotten to the other side of this, bald guys, men in treatment, men who've been wearing hats for years now, say the same thing almost universally: they spent months worrying, and once they committed to a hat that felt like theirs, they couldn't believe how little anyone reacted. The thing they feared most turned out to be mostly in their own head. You'll probably find the same.
Choosing Hats for Hair Loss, Alopecia, and Chemo
What bald men and men in treatment actually need
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Fabric matters more than you'd expect.
A scalp that's newly exposed is more sensitive than most men anticipate. Anything scratchy or stiff will tell you quickly. Soft cotton, organic cotton, and bamboo are the most forgiving materials for everyday wear and for sleeping. Our men's beanies and sleep caps are specifically chosen with this in mind.
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You'll likely need more than one hat.
Think about what your week actually looks like. Most men end up with a soft sleep cap for overnight, an everyday beanie or cap for daily wear, and a brimmed outdoor hat for time outside. Three hats, three different jobs. Over the years we've helped many men build that kind of simple, practical wardrobe.
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Your scalp needs sun protection now.
If you've never had to think about protecting your scalp from the sun before, that changes the moment your hair is gone. A brimmed hat with UPF 50+ fabric covers the areas sunscreen tends to miss, including your ears and the back of your neck.
Other options worth knowing about. If you're managing alopecia or hair loss from treatment, we also carry men's wigs and hairpieces for those who want a hair replacement option alongside or instead of headwear. And if eyebrow loss is part of the picture, our men's eyebrow solutions are worth a look. It's something most people don't think to mention until they need it.
Ready to find your hat?
Browse our full collection of men's hats, curated over 30 years.
Common Questions
Quick answers
Does wearing a hat cause hair loss?
No. Wearing a hat does not cause or accelerate hair loss of any kind, including pattern baldness, alopecia, or chemotherapy-related hair loss. The myth persisted because men who were already experiencing thinning happened to wear hats frequently. A properly fitting hat made from breathable fabric poses no risk to your scalp or remaining hair.
What is the best hat for a bald head?
It depends on when and where you're wearing it. For everyday wear, a soft cotton or bamboo beanie is the most comfortable option. For outdoors, a brimmed hat with UPF 50+ is important because a bare scalp burns faster than you'd expect and sunscreen often misses the ears and neck. For sleeping, a dedicated sleep cap with flat seams and an adjustable cuff makes a real difference. Most men with hair loss end up with two or three hats rather than one for everything.
What is the best hat for men going through chemotherapy?
Fabric is the first priority. A sensitive scalp reacts quickly to anything scratchy. Soft organic cotton and bamboo are the most forgiving materials. For daytime, a cotton or bamboo beanie looks natural and feels comfortable all day. For sleep, a dedicated sleep cap with an adjustable cuff and flat interior seams is worth having separately. For outdoor time, a brimmed hat with UPF 50+ protects the scalp from UV damage. We've been helping men through treatment since 1995 and our team is happy to help you figure out the right combination.
Should a hat leave a mark on your forehead?
A slight temporary line after a long day of wear is normal, similar to what a waistband leaves. But significant indentation or discomfort while wearing means the hat is too small. If a hat feels tight within the first few minutes, size up. A slightly large hat can always be fine-tuned with hat sizing tape or a sweatband reducer.
What can I do if my men's hat is too big?
Two products fix this without altering the hat. Hat sizing tape is a foam strip that adheres to the inside of the sweatband and takes up space evenly around the crown, good for hats that are a half size too large. A terry cloth sweatband reducer wraps around the interior band and adds cushion while reducing the fit. It also absorbs moisture, which is a bonus in warm weather. Both are reusable and work with most hat styles.
What hats work with a CPAP machine?
The best hats for CPAP users are close-fitting, soft, and have flat interior seams that don't press against the mask straps. Look for sleep caps and soft beanies in cotton or bamboo with no bulky cuffs near the mask area. Our organic cotton sleep cap is designed to be CPAP-compatible, with an adjustable cuff and flat stitching. See our full CPAP hat guide →
What hat style suits my face shape?
Round face: structured caps and medium brim styles add definition. Oval face: most styles work well. Square face: driver caps and flat caps balance a strong jawline. Long face: wider brims worn slightly lower add width and balance proportions. These are starting points, not rules. The best hat is still the one that feels right on you.
How to Build Your Hat Wardrobe
Most men need two or three, not one
Most men don't need a single perfect hat. They need two or three that cover different situations.
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Start with your everyday hat.
This is the one you reach for without thinking. A baseball cap, a driver cap, a soft men's beanie. Whatever fits your style and climate. Get the fit right and the material right for your weather, and this one carries most of the load.
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Add an outdoor hat if you spend time outside.
Gardening, golf, fishing, hiking, walking the dog in summer. A brimmed sun hat with UPF protection does a job your everyday cap can't. One good outdoor hat covers a lot of ground.
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Consider a sleep cap if you need one.
If you're dealing with hair loss from chemotherapy or alopecia, or just losing heat at night, a men's sleep cap makes a genuine difference. Many of our customers add this last and wish they'd done it sooner.
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Round out with a cold weather hat.
A fleece-lined or insulated hat for winter rounds out a practical wardrobe without overcomplicating it.
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30 Years in This Conversation
Headcovers.com was founded in 1995 after our founder went through cancer treatment and couldn't find headwear that actually worked. We've spent three decades helping men navigate hair loss, from the practical to the personal. When you call us, you reach our team in League City, Texas. We know these products and we understand what you're going through.
The right hat is the one you stop thinking about. It's just yours.
Shop men's hats for hair loss, sun protection, and everyday wear.
Curated for 30 years by people who understand what's at stake.
Understanding Hat Materials
What you're actually buying
The fabric a hat is made from affects how it feels, how long it lasts, and how comfortable it is for extended wear. When shopping online you can't touch the fabric, so here's what to know before you buy.
Cotton
The most versatile option. Breathable, washable, and gentle against the skin. Works year-round. Organic cotton is softer still and the best choice for scalp sensitivity.
Bamboo
Lightweight, naturally moisture-wicking, and exceptionally soft. Runs slightly cooler than cotton, which makes it a good choice for warm weather or anyone who runs warm.
Bamboo & Cotton Blends
A little more structure than pure bamboo, a little softer than standard cotton. Versatile across seasons.
Wool & Tweed
Retains heat and holds shape well. Go-to for fall and winter caps and driver hats. Wool felt is water-resistant and durable. Not ideal for sensitive scalps.
Fleece
The warmest option for close-fitting hats. Soft, insulating, and easy to care for. Our fleece beanies and sleep caps use mid-weight fleece that adds warmth without feeling heavy.
Straw, Toyo & Raffia
Warm weather materials in sun and outdoor hats. Lightweight and breathable, built for shade. Toyo is a lightweight paper-braid material that holds its shape well and is often more durable than natural straw for everyday wear.
Supplex & Nylon Blends
Technical fabrics used in performance outdoor hats. Lightweight, quick-drying, often moisture-wicking. Most of our UPF 50+ safari and hiking hats use these materials.
Caring for Your Hat
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Cotton & soft fabric hats. Many can be machine washed cold on the delicate cycle and laid flat to dry. Check the label first, but hand washing is almost always safe.
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Wool & structured hats. Brush gently to remove dirt. Avoid soaking, as it distorts the shape. Spot clean when possible.
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Straw & toyo hats. Keep them dry and don't crush the brim. Store flat or on a hook away from direct sunlight.
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Fleece & knit hats. Most are machine washable on a gentle cycle. Lay flat to dry to maintain shape and prevent stretching.
Storage tip. All hats last longer when stored somewhere they can hold their shape. Structured hats like driver caps and outback styles are best kept away from tight spaces that can crush the brim or crown.
Keep Learning
Types of Men's Hats
A visual guide to every hat style we carry: baseball caps, driver caps, bucket hats, outback hats, fedoras, beanies, and more, with notes on when and how to wear each one.
Read the guide →
Best Hats for CPAP Users
A guide to finding the right sleep cap to wear under your CPAP mask. What to look for, what to avoid, and which styles our customers come back for year after year.
Read the guide →
© 2026 Headcovers Unlimited, Inc. · All rights reserved. · Men's Hat Buying Guide
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