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The Best Hats for Traveling

The Best Hats for Traveling

Travel Hats Made Easy: What to Pack vs What to Wear

Quick answer: Pack soft, low-structure hats in your suitcase. Wear your most structured hat through the airport so it keeps its shape.

If you like bringing more than one hat, this simple rule keeps your favorites looking sharp and saves space in your bag.

What to Pack (Low-Structure, Bounce-Back Hats)

Richardson 935 — Performance, Packable, Water-Resistant

The 935 is unstructured and flexible, so it packs flat without creasing. It’s quick-dry, breathable, and built for sweaty, active travel days.

Shop the 935 “Paddle & Chill” Performance Hat

Richardson 256 — Soft-Structured Rope Hat

Low profile, five-panel, and soft enough to tuck in a packing cube. The 256 rebounds well after the flight and looks clean for city days or beach walks.

Shop the 256 “Mountain West” Rope Hat

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What to Wear (Keep the Structure on Your Head)

Richardson 168 — Seven-Panel, Flat Bill

The 168 holds its lines. Wear it gate-to-gate so the crown and bill don’t get crushed in transit.

Shop the 168 “Mountain East”

Imperial Rope Hats — Statement Look, Travel-Friendly

A structured, mid-profile silhouette with that classic rope detail. Great for flights and days when you want a sharper look out of the airport.

Shop the Imperial “Island Breeze”

Side view of the Island Breeze Hat in Hawaiian Rainforest, highlighting the unique rainforest-themed print, structured profile, and classic rope detail. The hat includes a genuine leather patch with a palm tree engraving and an adjustable leather strap for a custom fit.

How to Pack a Hat in a Suitcase (Step-by-Step)

  1. Choose the right hat: Unstructured or soft-structured models (think 935 or 256) are best for luggage.
  2. Fill the crown (optional): For soft crowns, you can roll a T-shirt and nest it lightly to help keep shape.
  3. Lay the bill flat: Place the hat crown-up with the bill along a packing cube edge.
  4. Surround with soft layers: Pack tees or a hoodie around the sides so the crown isn’t crushed from above.
  5. Avoid heavy pressure: Don’t put shoes or a toiletry kit on top of your hat.

Pro tip: If you’re bringing multiple hats, wear your most structured one and pack the softest. If you use a hat clip, secure extras to your backpack so they travel outside your bag (not for fitted hats without a strap).

Leather hat clip by Outer Wings attached to a backpack with a hat securely hanging from it. The clip features a strong leather loop and a 360-degree swivel quick link keychain, demonstrating its durability and functionality for convenient hat carrying.

Travel Hat Clip: Carry Extra Hats Without Using Bag Space

Bring more than one hat without crushing anything. Our leather Travel Hat Clip secures to a backpack, duffel, or suitcase so your hats ride outside your bag and keep their shape.

Why Travelers Love It

  • Saves space: Free up room in your carry-on by hanging hats externally.
  • Protects shape: No more flattened crowns or bent bills in a packed suitcase.
  • Quick access: Swap hats at the gate, beach, or trailhead without digging through your bag.

How It Works

  • Clip + loop: A sturdy hardware clip attaches to your bag; a strong leather loop (about 1.5") threads through your hat’s snapback/webbing strap.
  • Capacity: Holds 1–3 hats comfortably, depending on profile and strap style.
  • Compatibility: Works with snapback and webbing-strap hats (112, 115, 256, 935, Imperial rope). Not ideal for fitted hats without a strap to pass through.

Travel Tips

  • Wear your most structured hat on the plane; clip your softer backups to your bag.
  • If rain is in the forecast, clip hats to the side of your pack under a jacket or pack cover.
  • For security checks, keep the clip attached to your bag and lift hats off the loop—fast in, fast out.

Care & Maintenance

  • Wipe the leather loop clean with a damp cloth; let it air dry.
  • Occasionally condition the leather to keep it supple if you travel often in sun or salt air.

Bottom line: Pair this clip with one structured hat on your head and a soft, packable backup on the loop for a simple, travel-proof setup.

Trip Scenarios: The Right Hat for the Day

Hot & Humid or High-Output Days

Casual Sun-Heavy Days

City Nights & Dressier Plans

Chilly Mornings & Flights

  • Best pick: A beanie packs tiny, adds warmth on planes and early starts.
  • Browse Beanies

Quick Picks You Can’t Go Wrong With

Side view of the Outer Wings leather hat clip in use, showing a hat hanging from a backpack. The clip's robust design with Chicago rivets and quick link keychain ensures a secure hold, making it ideal for outdoor activities and travel.

FAQs: Travel & Packing

Can I pack a flat-bill hat in my suitcase?

You can, but it’s safer to wear structured, flat-bill styles (like the 168) so the bill and crown don’t warp. Pack a soft 935 or 256 instead.

What if I only want to bring one hat?

Choose versatility: the 256 Mountain West travels well, works in sun, and looks good dressed up or down.

Best hat for sweaty, active trips?

Performance fabric and breathability win. The 935 Paddle & Chill is quick-dry and packable.

Headed somewhere breezy or coastal?

Keep structure on your head—fly in the Imperial Island Breeze, pack a softer backup.

Should I bring a beanie too?

Yes if mornings or flights run cold. It takes no space and adds instant warmth. Browse Beanies

Wrap-Up

Wear your structured favorite on the plane. Pack a soft, bounce-back hat in your bag. Between the 935, 256, 168, and Imperial rope, you’ll cover travel days, beach days, and nights out—without sacrificing style or suitcase space.

Want to see everything in one place? Browse all leather patch hats.