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The Hat Drop: Trucker Hats and Beanies for Spring 2026

Aerial view of boats at a busy harbor pier

The Dockhead Crew |

April is the transition month for headwear. The beanie doesn't retire completely until May — the mornings still earn it — but the trucker hat starts making its presence known in the afternoons. By the end of April, the ratio has flipped and the trucker hat is your daily driver with the beanie as backup.

Here's the full Dockhead headwear lineup for spring and why each one earns its place.

The Trucker Hats

Dockhead Trucker Hat — $29.95

The Dockhead Trucker Hat is the signature piece of the headwear lineup. Structured front panel with the Dockhead graphic, breathable mesh back, and available in five colorways: navy/white, pink, moss/khaki, black, and black/white. The navy/white is the classic; the moss/khaki is for the outdoorsy crowd; the pink is a statement. All $29.95.

This is the hat for April afternoons, full dock days, and the first weekend where you don't need to think about your head situation at all. It handles sun, it photographs well in natural light, and it pairs with everything from swimwear to a hoodie depending on the temperature.

Iconic Dockhead Trucker Hat — $29.95

The Iconic Dockhead Trucker Hat is the cleaner, more minimal version — available in heather/black and white. Same construction as the standard Trucker Hat, slightly more understated graphic presence. This is the hat for the person who wants the Dockhead look without the full announcement — or for pairing with more graphic-forward outfits where the hat shouldn't compete.

The Beanies

Dockhead Waffle Beanie — $21.95

The Dockhead Waffle Beanie transitions from full-time winter headwear to morning-only spring essential in April. Keep it in the bag. You'll use it before 10am more often than you expect. Available in black, navy, heather charcoal, and heather grey at $21.95 — the most affordable piece in the Dockhead catalog.

Iconic Dockhead Cuffed Beanie — $21.95

The Iconic Dockhead Cuffed Beanie is the more styled option — classic double-cuff construction available in navy, dark grey, heather grey, baby pink, and white. In spring, this one goes on for cool evenings and early morning dock sits when the waffle knit feels like too much of a commitment to the cold.

Spring Headwear Strategy

The April headwear approach: trucker hat in the bag from the start of the day, beanie on for the morning, hat swap at midday, beanie back out for the evening if needed. It sounds like too much planning for a hat but it happens naturally once you have both available.

The May simplification: trucker hat all day, beanie in the emergency pocket of the boat bag.

All Dockhead headwear is made to order through Printful. No seasonal stockouts, no end-of-winter clearance. The beanie available in January is available in April at the same quality and price — because it's made when you order it, not before.

Shop the full headwear lineup at TotalDockhead.com/collections/hats.

Content creators who capture the spring-to-summer hat transition — the Dockhead Collabs program is open. Headwear content is some of our most reliable engagement across seasons.

Frequently Asked Questions

What hats does Dockhead sell?

Dockhead sells two trucker hat styles (Dockhead Trucker Hat and Iconic Dockhead Trucker Hat, both $29.95) and two beanies (Dockhead Waffle Beanie and Iconic Dockhead Cuffed Beanie, both $21.95). All are made to order through Printful.

What is the best spring hat for boating?

The Dockhead Trucker Hat ($29.95) is the ideal spring boating hat — structured front for shape, breathable mesh back for ventilation, and available in five colorways including the popular navy/white.

When should I switch from a beanie to a trucker hat?

The natural transition happens when afternoon temperatures consistently reach the mid-60s or above. For most of the US, this is mid-to-late April. Keep both available through May as mornings and evenings may still warrant the beanie.

Are Dockhead hats made sustainably?

All Dockhead hats are made to order through Printful — no pre-manufactured inventory, no overproduction waste. Every hat is produced specifically for your order, which is a meaningfully more sustainable approach than seasonal mass manufacturing.

What sizes do Dockhead hats come in?

Dockhead trucker hats are one-size-fits-most with an adjustable snapback closure. Beanies are one-size stretch knit. Check individual product pages at TotalDockhead.com for fit details.

What colorways are available for the Dockhead Trucker Hat?

The Dockhead Trucker Hat is available in navy/white, pink, moss/khaki, black, and black/white at $29.95. The Iconic Dockhead Trucker Hat is available in heather/black and white.

What is the difference between the Dockhead Waffle Beanie and the Cuffed Beanie?

The Waffle Beanie is lighter and more packable — best for the boat bag and as a casual morning piece. The Cuffed Beanie is more structured with a classic double-cuff look — better for intentional cold-weather styling and evening dock situations.