Headwear Buying Guide: How to Choose Hats, Caps, and Beanies for Game Night

Quick answer

For most fans, a dad hat is the easiest everyday choice because it adjusts in back and pairs with almost anything. If you want warmth and a relaxed look, choose a beanie. If you prefer a structured, sporty shape, choose a snapback or fitted cap. Match the hat to the event: dad hats for game night, beanies for cold conventions, and caps for outdoor meetups.

Headwear is the fastest way to show your fandom without wearing a full costume. But the wrong fit or fabric can make a long convention day miserable. This guide breaks down the main hat styles, what each one does well, and how to pick the right one for your head and your plans.

You will also see how specific Critical Role pieces fit into those categories, from an adjustable dad hat to a cozy hoodie. Use the decision rules and fit guidance below to choose once and wear it often.

The three main headwear shapes (and what they do best)

Dad hats have a soft, unstructured crown and a curved brim. They adjust in back, so one size covers most heads. They look casual and are easy to pack. Beanies are knit and stretchy, designed for warmth. They sit close to the head and can be worn cuffed or slouchy. Snapbacks and fitted caps have a structured front and a flat or curved brim. They hold their shape and read as more sporty or streetwear.

The trade-off is structure versus packability. Structured caps look sharp but can dent in a bag. Dad hats and beanies fold flat. For travel or a full day at a convention, soft styles are usually more comfortable.

• Soft crown = casual look, easy packing.
• Structured crown = sharper shape, less forgiving in a bag.
• Knit beanie = warmth first, style second.

How to choose a beanie that actually fits

Beanies stretch, but they are not one-size-fits-all in practice. Measure your head circumference just above your ears with a soft tape. Most adult beanies fit 21 to 24 inches comfortably. If you are between sizes, size up for a slouchy look or size down for a snug, cuffed fit. Acrylic and wool blends hold shape better; cotton blends feel lighter but can stretch out over time.

For conventions, a thinner beanie works indoors because it vents heat. For outdoor winter events, a thicker ribbed knit traps warmth. If you wear glasses, choose a beanie that sits above the temple arms so it does not press them into your head.

• Measure above the ears, not across the forehead.
• Cuff it for a tighter fit; leave it long for slouch.
• Thin knit for indoors, thick rib for cold outdoors.

Dad hats vs. snapbacks vs. fitted caps

Dad hats win on comfort and adjustability. The soft crown conforms to your head, and the strapback closure covers a wide size range. Snapbacks offer a similar adjustable fit but with a stiffer front panel that stands up. Fitted caps have no adjustment, so you need your exact size. They look the most polished but are the least forgiving if your size is off or your hair volume changes.

For game night at a friend's house, a dad hat is the low-effort choice. For a tournament or a meetup where you want a sharper silhouette, a snapback works. For daily wear where you rarely adjust your hat, a fitted cap is fine if you know your size.

• Adjustable closure = safer online purchase.
• Structured front = more visual impact, less packability.
• Fitted = measure twice, buy once.

Fabric and weather: what to wear when

Cotton twill is the standard for dad hats and caps. It breathes, holds a curve, and handles light rain. Polyester blends dry faster and resist fading, which helps if you wear the same hat often. Wool and acrylic beanies are for cold. If you run hot, choose a lighter knit or a cap with a mesh back.

For conventions, indoor halls get warm. A cotton dad hat is easier to wear all day than a heavy beanie. If you are queuing outside in winter, a beanie plus a hoodie gives you layers you can remove. A hoodie with a hood also doubles as emergency headwear if you forget your hat.

• Cotton for breathability, polyester for durability.
• Wool and acrylic for cold; mesh for heat.
• Layer a hoodie under a beanie for flexible warmth.

Headwear for conventions: practical checks

Convention days are long. Choose headwear you can forget you are wearing. That means no tight bands, no heavy brims that block your view in a crowded hall, and no dark colors that show sweat. A dad hat with a curved brim keeps sun and lights out of your eyes without hiding your badge or your face.

If you plan to buy merch at the event, bring a packable hat so you have room in your bag. A beanie takes almost no space. A structured cap does. Also check the event's bag policy: some venues ask you to remove hats at security, so a style that is easy to take on and off helps.

• Curved brim = better visibility in crowds.
• Packable styles save bag space for merch.
• Avoid tight bands if you wear headphones or glasses.

Caring for headwear so it lasts

Most caps and dad hats are spot-clean only. Use a damp cloth with mild soap and air-dry. Do not put a structured cap in the washing machine; the brim can warp. Beanies made of acrylic or wool can be hand-washed in cold water and laid flat to dry. Heat is the enemy: it shrinks wool and breaks down elastic closures.

Store hats on a shelf or hook, not crushed under books. If you stack them, put soft beanies on top and structured caps on the bottom. For long storage, stuff the crown with tissue paper to hold its shape.

• Spot-clean caps; hand-wash beanies.
• Air-dry only; no dryer.
• Stuff structured crowns to prevent dents.

Decision rules: pick your headwear in four questions

• Do you need warmth or just style?: If the temperature is below 50°F or you will be outside at night, choose a beanie. If you are indoors or in mild weather, choose a dad hat or cap. Warmth first = beanie. Style first = dad hat or cap.
• Will you wear it for more than four hours?: Long wear favors soft, adjustable styles. A structured snapback or fitted cap can feel tight after a few hours, especially if you wear glasses or headphones. All-day comfort = soft crown and adjustable closure.
• Do you need to pack it in a bag?: Beanies and dad hats fold flat. Structured caps need space or they dent. If you are traveling to a convention, prioritize packability. Packable = beanie or dad hat.
• Do you want to show a specific fandom?: Embroidery and prints last longer than stickers or pins on fabric. Choose a hat with the design built in if you want it to survive daily wear. Use pins for interchangeable flair. Permanent fandom = embroidered or printed hat. Flexible fandom = pins.

Critical Role headwear and layers that work together

• Age of Umbra “Umbies” Dad Hat: This black dad hat features an edgy "UMBIES" design embroidered across the front in striking, heavy metal-style font. It is an adjustable style that identifies you as one who is at home in the dark. A dad hat is the most adjustable and packable option here, making it a safe pick for game night or a convention day when you want low-maintenance fandom.
• Vox Machina Hoodie: This maroon fleece hoodie is made of 80% cotton and 20% polyester, with a Vox Machina design printed on the back and the Critical Role logo on the front-left breast. It is described as extra soft. When the weather turns cold, a hoodie adds a hood for warmth and a layer you can remove indoors. The cotton-poly blend balances breathability and durability.
• Critical Role Chibi Pin No. 13 - PERCIVAL FREDRICKSTEIN VON MUSEL KLOSSOWSKI DE ROLO III: This 1.75-inch hard enamel pin is made of silver plated zinc alloy and is pin #13 of the Chibi Pin series. It is designed to accompany you on your bag or jacket. A small pin adds character to a plain hat or bag without changing the fit. It is a low-cost way to customize headwear or a hoodie.
• Tankard Wrap: What the F is Up with That?: This deep teal tankard wrap is made of polyurethane leather with debossed text. It fits tankards measuring 10.5-12 inches in circumference. The Critical Role Tankard is sold separately. Not headwear, but it is a useful reminder that fit matters across gear. Always check the stated circumference before buying an accessory that has to fit a specific object.

Fit guidance: who should buy which style

Best for

• Fans who want an adjustable, packable hat for game night or conventions
• People who wear glasses or headphones and need a soft, non-pressing band
• Anyone buying headwear online who cannot try it on first

Not for

• Shoppers who need a structured, sporty silhouette for a specific outfit
• Cold-weather outdoor use where a knit beanie is the only warm option
• People who want a fitted cap and already know their exact size

Choose headwear by fit and function first, then by fandom. A dad hat covers most everyday needs, a beanie handles cold, and a structured cap delivers a sharper look. Check the closure, fabric, and care instructions before you buy, and your hat will stay comfortable and recognizable for years.