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Sunday Afternoons
Sunday Afternoons Islander Hat

Sunday Afternoons Islander Hat

4.6· 29 ratings

Best price now

$44.00at Massey's OutfittersObserved at 4:37 PM

19% under what the other stores charge

Compared across 5 stores. Prices are checked against each store and labelled with when.

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Our take on the Sunday Afternoons Islander Hat

The Sunday Afternoons Islander is a straw fedora with a 3-inch brim and a UPF 50+ rating, made in Mexico from natural tripilla straw. It pairs a classic fedora profile with an elasticized sweatband and an adjustable leather chin strap. The best new price is $44.00 at Massey's Outfitters as of November 4, 2026, with 5 stores listing it new.

Best forBeach and resort wearEveryday sun protectionFedora-style hat wearersTravelers who want packable shade
Pros
  • UPF 50+ sun rating
  • 3-inch brim shades the face and neck
  • Natural tripilla straw, made in Mexico
  • Elasticized sweatband for a custom fit
  • Adjustable leather chin strap holds it in wind
Cons
  • Sizing runs inconsistent between sizes
  • Medium can feel snug, especially over braids
  • Straw needs spot cleaning only
  • Limited color and size options

Sunday Afternoons Islander Hat prices at every store

  • Chapeaux MichelleNew

    In stock

    $54.00Free shippingObserved at 4:37 PM
    Visit store
  • Massey's OutfittersNew

    Availability unknown

    $44.00Observed at 4:37 PM
    Visit store
  • AmazonNew

    Availability unknown

    As an Amazon Associate, Deal.ai earns from qualifying purchases.

    $54.00Free shippingObserved at 4:37 PM
    Visit store
  • WalmartNew

    Out of stockSold by WhoIsCamera

    $47.99Free shippingObserved at 4:37 PM
    Visit store
  • Confluence RunningNew

    Out of stock

    $54.00+ $5.99 shippingObserved at 4:37 PM
    Visit store

Sunday Afternoons Islander Hat price history

Lowest price we've seen: $44.00 on Nov 4 at Massey's Outfitters. Tracked across 5 stores since Nov 4.

What reviewers say

Rated 4.6 out of 5 from 29 ratings, owners call the Islander well made, lightweight and stylish, with a brim that holds its shape and draws compliments. The main complaint is fit: sizing is inconsistent, and the medium can feel tight.

Pros
  • Well made and sturdy
  • Stylish fedora look
  • Comfortable and lightweight
  • Good sun coverage from the brim
Cons
  • Inconsistent sizing
  • Medium fits snug, tight with braids
  • Large reported as oddly fitting

From Massey's Outfitters

  • Classic fedora profile
  • UPF 50+ sun rating blocks harmful UV rays
  • Adjustable leather chin strap/hatband for a secure fit
  • Elasticized sweatband provides a custom, comfortable fit
  • Made in Mexico from local fibers
  • 3-inch (8 cm) fedora brim
Materials
100% natural tripilla straw
Fit
Secure and personalized fit with adjustable leather chin strap/hatband and elasticized sweatband
Sizing
Reviews are mixed: some say it runs large and suggest sizing up if between sizes, while others found the medium snug and the large oddly fitting.
Returns
One reviewer reported sending back a medium that was too big and not receiving a refund.
Shipping
Same-day local delivery available; buy now and pick up at store; reserve online and pay at store.

About the Sunday Afternoons Islander Hat

A sturdy straw hat in a classy, stylish profile, the Islander Hat is made in Mexico from 100% natural tripilla straw. With the UPF 50+ sun rating you expect and our elasticized sweatband, this classic hat provides ample shade and a custom fit whether you're walking the beach or out on the town.

What buyers say

Buyers like
  • Great quality and well made
  • Super cute, stylish look
  • Comfortable to wear
  • Brim holds its shape and offers good sun coverage
  • Lightweight
  • Draws compliments
Buyers complain about
  • Sizing inconsistent: large described as oddly fitting
  • Medium can fit snug, tight with braids
  • One reviewer did not receive a refund after returning

Specifications

Brim width
3" brimSource
Sun protection
UPF 50+Source
Material
Natural tripilla strawSource
Sweatband
Elasticized sweatbandSource

Questions and answers

Is the Sunday Afternoons Islander Hat worth it?
At $44.00 at Massey's Outfitters as of November 4, 2026, it is a reasonable price for a UPF 50+ straw fedora with a leather chin strap. Buyers rate it 4.6 out of 5 and praise the build and shape.
How does the Islander compare with a canvas or synthetic sun hat?
Straw looks dressier and breathes well, but it is not crushable or machine washable like many synthetic hats. Spot clean only, and expect the straw to soften with wear.
What size should I order?
Sizing is the most common complaint. The medium can fit snug, especially over braids, and one large was described as oddly fitting. Measure your head and size up if you are between sizes.
Does it stay on in wind?
Yes. It has an adjustable leather chin strap and hatband, so you can tighten it for beach walks or boat rides.
What is in the box?
The hat itself, with the leather chin strap and hatband attached. No hat box or travel case is included.
When is the Islander Hat cheapest?
The best new price found is $44.00 at Massey's Outfitters as of November 4, 2026, across 5 stores. Straw hats usually drop in late summer and early fall.
Where is the Sunday Afternoons Islander Hat cheapest?
At Massey's Outfitters, for $44.00, 19% under what the other stores charge, as of our latest check.
What do buyers say about the Sunday Afternoons Islander Hat?
Rated 4.6 out of 5 from 29 ratings. Buyers like: Great quality and well made; Super cute, stylish look; Comfortable to wear. Common complaints: Sizing inconsistent: large described as oddly fitting; Medium can fit snug, tight with braids.
Where can I buy the Sunday Afternoons Islander Hat?
5 stores we checked sell it, including Massey's Outfitters, Walmart, Chapeaux Michelle, Confluence Running, Amazon.

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Product dimensions
15" L x 14" W x 5" HSource
Country of origin
Made in MexicoSource
Care
Spot CleanSource