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Legacy

Legacy hats are known for their classic, vintage-inspired style and comfortable broken-in feel. With washed cotton fabrics, unstructured fits, and timeless designs, Legacy caps are a popular choice for custom embroidery and retail-quality branded merchandise. Their laid-back look makes them especially popular for golf courses, breweries, lifestyle brands, and resort shops.

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'47Adams HeadwearAS ColourBlvnk HeadwearCap AmericaCarharttDeckyFlexfitImperialLegacyMegaCapNew EraNikeOakleyOGIOOtto CapOutdoor CapPacific HeadwearPort AuthorityRichardson SportsTravis MathewYupoongZapped Headwear
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Tie-Dyed Ribbed Beanie
Style: KTDRB
Tie-Dyed Ribbed Beanieas low as $21.67
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The Caddy Adjustable Cap
Style: CADDY
The Caddy Adjustable Capas low as $22.02
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Mid-Pro Snapback Trucker Cap
Style: MPS
Mid-Pro Snapback Trucker Capas low as $17.82
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Dashboard Trucker Cap
Style: DTA
Dashboard Trucker Capas low as $17.12
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Laguna Cap
Style: LTA
Laguna Capas low as $16.07
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The Chill Cap
Style: CHILL
The Chill Capas low as $18.87
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Relaxed Twill Dad Hat
Style: EZA
Relaxed Twill Dad Hatas low as $17.82
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Old Favorite Trucker Cap
Style: OFA
Old Favorite Trucker Capas low as $18.87
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Heritage Twill Cap
Style: HTA
Heritage Twill Capas low as $18.87
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Tacticool Cap
Style: TACT
Tacticool Capas low as $18.87
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The Cut Above Cap
Style: CUT
The Cut Above Capas low as $24.12
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About the Brand

Legacy Hats — Vintage Roots. Retail-Quality Craft.

Legacy hats trace their roots back to 1992, when two law school roommates set out to build a better-fitting cap than anything they could find at their campus bookstore. What started in an off-campus apartment became one of the most respected names in vintage-inspired headwear — known for washed fabrics, unstructured fits, and that signature broken-in feel you can't fake. Today, Legacy supplies high-end headwear to colleges, resorts, golf courses, and lifestyle brands across the U.S., staying true to their retro roots while keeping pace with modern trends.

🏝

Vintage Roots

Founded on the idea that a great hat should feel like it's already been lived in — washed fabrics and unstructured fits that deliver a naturally broken-in look from day one.

⛳

Resort & Lifestyle Favorite

A go-to for golf courses, breweries, resort shops, and lifestyle brands that want retail-quality headwear with a relaxed, effortless aesthetic.

🎯

Decoration-Ready

Washed cotton fabrics and clean unstructured fronts that pair beautifully with embroidery and custom patches — ideal for logos that need to feel at home on a vintage-style cap.

Popular Styles

Popular Legacy Hat Styles

From washed trucker hats to vintage snapbacks and cozy beanies, Legacy's lineup spans styles built for the golf course, the taproom, and everywhere in between. These are the styles our customers reach for most when building lifestyle brands, resort merchandise programs, and custom Legacy hat collections.

Legacy KTDRB Tie-Dyed Ribbed Beanie
KTDRB

Tie-Dyed Ribbed Beanie

A bold, tie-dyed ribbed beanie that brings vintage color and texture to cold-weather merchandise. A standout for lifestyle brands, resort shops, and seasonal merchandise drops.

Shop KTDRB →
Legacy CADDY The Caddy Adjustable Cap
CADDY

The Caddy Adjustable Cap

A clean, relaxed adjustable cap made for the course and beyond. Its refined silhouette and washed finish make it a natural fit for golf clubs, resort pro shops, and upscale lifestyle programs.

Shop CADDY →
Legacy DTA Dashboard Trucker Cap
DTA

Dashboard Trucker Cap

A vintage-style trucker with a mesh back and relaxed profile. Perfect for outdoor lifestyle brands, craft breweries, and anyone building a custom trucker hat program with laid-back appeal.

Shop DTA →
Legacy MPS Mid Pro Snapback Trucker Cap
MPS

Mid Pro Snapback Trucker Cap

A mid-profile snapback trucker with classic structure and mesh back breathability. A versatile blank canvas for embroidery and custom patches across outdoor, lifestyle, and sport programs.

Shop MPS →
Legacy CHILL The Chill Cap
CHILL

The Chill Cap

Relaxed, easygoing, and built for everyday wear. The Chill Cap is a fan favorite for resort merchandise, poolside branding, and lifestyle collections where comfort is the whole point.

Shop CHILL →
Legacy HTA Heritage Twill Cap
HTA

Heritage Twill Cap

A refined twill cap with heritage styling and an unstructured fit. Ideal for upscale lifestyle branding, corporate gifting, and custom embroidery programs that demand a polished yet relaxed look.

Shop HTA →
Custom Legacy Hats

Put Your Brand on a Hat People Actually Want to Wear

Adding your logo to a custom Legacy hat associates your brand with well-crafted, retail-quality headwear. Frequently worn in everyday settings — on the course, at the brewery, around the resort — these hats are the perfect billboard for your brand. Embroidery and custom patches both shine on Legacy's washed fabrics, giving your logo a textured, dimensional finish that looks like it belongs there. Buyers who love the Legacy aesthetic also tend to gravitate toward Imperial and '47 Brand for similar vintage-leaning styles.

With The Monterey Company, you can add your logo or design to a wide variety of custom hats for any occasion. We offer multiple hat styles, from relaxed sun hats ideal for lounging by the pool or in the garden, to flat bill hats that stand out at ballgames, concerts, or festivals. Our collection also includes a range of top brands in the headwear industry such as Nike, Yupoong, New Era and more, all of which will make your branding more appealing while maintaining comfort and versatility.

Start Your Custom Order →

Decoration Methods

Embroidery Custom Patches Woven Labels Heat Transfer Leather Patches

Turnaround & Minimums

Standard turnaround runs 2–3 weeks from artwork approval. Rush options available. Low minimums make custom Legacy hats accessible for boutique resort shops and large-scale brand programs alike.

How It Works

Choose your style, submit your artwork, and we handle the rest — from digitizing to decoration to delivery. Our team will send a proof for approval before anything goes into production.

Getting Started

How To Order

Start here
01
🎯

Select

Browse our collection and choose your preferred style.

02
📤

Upload

Upload your custom design and receive a tailored digital mockup from our team.

03
✅

Approve

Once you approve our artwork, production begins immediately — no delays.

Fast turnaround
04
📦

Receive

Patch products arrive in ~4 weeks. Embroidery takes ~2 weeks.

Explore More

Explore more styles from The Monterey Company

We carry a full range of branded headwear for every occasion, team, and budget.

Frequently Asked Questions

What is the production timeline for custom Legacy hats?
The average production time for custom Legacy hats with embroidery is just two weeks while Legacy hats with custom patches average four weeks.
Can I get my order rushed?
Yes, we offer rush services depending on the current production schedule. Please contact our customer service team before placing your order to ensure we can meet the deadline.
What is the minimum amount of custom Legacy hats I can order?
Our minimum order requirement is just 24 hats. Feel free to mix and match different hat colors with your order as well!
Do you offer decorated Legacy hat samples?
Yes, we do. The cost depends on the cap style, decoration method, and design. Please get in touch with our sales team for a customized sample quote. If you are curious about the best type of patch for your design, we offer free shipping on sample packages. Just ask our customer service team (free shipping on samples is limited to the United States only).
Can I add my company logo to custom Legacy Hats?
Yes. We can embroider your design or apply a custom patch to any Legacy style for a polished yet relaxed look.
What makes Legacy Headwear stand out from other hat brands?
Legacy is known for its signature washed fabrics, unstructured crowns, and timeless designs that deliver an effortlessly worn-in feel.
Can I create a vintage or distressed effect with my custom design?
Yes. Legacy’s garment-washed materials naturally produce a vintage look, and we can recommend decoration methods that complement the worn-in style.