Skip to content

Adjustable Size Hats

  • Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons Accessories
    Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats Fedora Hat Jeanne Simmons Accessories JS8439BZ Bronze Small (56 cm)

    Petite Straw Fedora Hat with Black Band - Jeanne Simmons Hats

    $ 24.00

    Discover timeless summer style with this petite straw fedora, expertly crafted for smaller head sizes. The soft paper braid construction offers bre...

    View full details
    $ 24.00
  • Little Bucket Hat with Split Brim - Jeanne Simmons Hats Cloche Jeanne Simmons Accessories
    Little Bucket Hat with Split Brim - Jeanne Simmons Hats Cloche Jeanne Simmons Accessories JS9160 Brown

    Little Bucket Hat with Split Brim - Jeanne Simmons Hats

    $ 20.00

    This standout women’s packable sun hat was designed for effortless summer style. The 2.5" shapeable brim lets you customize your look—tilt it, curv...

    View full details
    $ 20.00
  • Charlie Trilby by Wallaroo Hat Company Fedora Hat Wallaroo Hats
    Charlie Trilby by Wallaroo Hat Company Fedora Hat Wallaroo Hats

    Charlie Trilby by Wallaroo Hat Company

    $ 57.00

    The Charlie Unisex Trilby offers a timeless shape with a contemporary feel, featuring a structured crown and shorter brim for a refined, easygoing ...

    View full details
    $ 57.00
  • Lady Jane by Wallaroo Hat Company Kettle Brim Hat Wallaroo Hats
    Lady Jane by Wallaroo Hat Company Kettle Brim Hat Wallaroo Hats

    Lady Jane by Wallaroo Hat Company

    $ 71.00

    The Lady Jane is adorned with a printed scarf with Jane Seymour's artwork. It is a lovely upturned brim that frames the face beautifully, giving th...

    View full details
    $ 71.00
  • Carkella Lauren by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Lauren by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Lauren by Wallaroo Hat Company

    $ 71.00

    The Lauren brings classic safari styling to modern sun protection with its structured crown and wide, flattering brim. Lightweight and breathable, ...

    View full details
    $ 71.00
  • Two Tone Straw Summer Hat for Petite Heads - Sunny Dayz™ Facesaver Hat Sun N Sand Hats HK448 Natural Small (54 cm)

    Two Tone Straw Summer Hat for Petite Heads - Sunny Dayz™

    $ 28.75

    Discover effortless sun protection with the Sunny Dayz™ Two Tone Straw Summer Hat, thoughtfully designed for petite frames. This elegant style feat...

    View full details
    $ 28.75
  • Carkella Kerrigan by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Carkella Kerrigan by Wallaroo Hat Company Safari Hat Wallaroo Hats

    Carkella Kerrigan by Wallaroo Hat Company

    $ 71.00

    The Kerrigan blends the classic safari silhouette with Carkella’s smart magnetic emblem system. The durable woven fabric with contrasting stitching...

    View full details
    $ 71.00
  • Fine Braid Straw Beach Hat, M/L size - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats
    Fine Braid Straw Beach Hat, M/L size - Boardwalk Style Wide Brim Sun Hat Boardwalk Style Hats

    Fine Braid Straw Beach Hat, M/L size - Boardwalk Style

    $ 32.00

    Experience effortless sun protection with this elegant fine braid straw beach hat. Crafted from 100% paper raffia, it features a softly domed crown...

    View full details
    $ 32.00
  • St. Lucia by Wallaroo Hat Company Safari Hat Wallaroo Hats
    St. Lucia by Wallaroo Hat Company Safari Hat Wallaroo Hats

    St. Lucia by Wallaroo Hat Company

    $ 69.00

    The St. Lucia Safari Hat combines a relaxed outdoor look with exceptional sun protection. Its wide brim provides generous UPF 50+ shade, while the ...

    View full details
    $ 69.00
  • Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat Gambler Hat Sun N Sand Hats HH2703C Natural M/L (58 cm)
    Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat Gambler Hat Sun N Sand Hats

    Flat Crown Up Brim Sun Hat - Sun 'N' Sand Hat

    $ 45.00

    Take command of your sun protection with this striking gaucho-inspired hat that empowers you to stay safe without sacrificing style. The bold flat ...

    View full details
    $ 45.00
  • Wide Brim Sun Hat with Neck Flap - Juniper UV Blocking Hats Cap MegaCI
    Wide Brim Sun Hat with Neck Flap - Juniper UV Blocking Hats Cap MegaCI J7273-GREY Grey M/L

    Wide Brim Sun Hat with Neck Flap - Juniper UV Blocking Hats

    $ 36.00

    Shield yourself from the sun with confidence in this versatile wide-brim hat designed for active lifestyles. Engineered with UPF50+ UV-blocking fab...

    View full details
    $ 36.00
  • Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™ Gambler Hat Caribbean Joe HCJ242B Tan Medium (57 cm)
    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™ Gambler Hat Caribbean Joe HCJ242S Natural Medium (57 cm)

    Bangkok Toyo Gaucho Hat with Aztec Trim - Caribbean Joe™

    $ 38.00

    Elevate your sun style with this charming gaucho hat from Caribbean Joe™. Crafted from soft, breathable bangkok toyo, it features a distinctive sun...

    View full details
    $ 38.00
  • Chicopee Rough Cotton Split Brim Cloche Hat - Callanan Hats Cloche Callanan Hats
    Chicopee Rough Cotton Split Brim Cloche Hat - Callanan Hats Cloche Callanan Hats cr316bk Black OS

    Chicopee Rough Cotton Split Brim Cloche Hat - Callanan Hats

    $ 39.00

    Meet your new summer essential—a delightful cloche hat woven from rough cotton and linen that's ready for adventure. The shapeable split brim stret...

    View full details
    $ 39.00
  • Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats
    Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat Bolero Hat Sun N Sand Hats hh2137C mf Moss green Medium (57 cm)

    Cativa Flat Crown Floppy Hat - Sun 'N' Sand Hat

    $ 37.00

    Embrace effortless summer style with this stunning flat crown gaucho hat, designed for those who refuse to compromise on sun protection or sophisti...

    View full details
    $ 37.00
  • Up Turned Brim Classic Sun Hat - Sun 'N' Sand Hats Kettle Brim Hat Sun N Sand Hats
    Up Turned Brim Classic Sun Hat - Sun 'N' Sand Hats Kettle Brim Hat Sun N Sand Hats HH803M Hot Pink Medium (57 cm)

    Up Turned Brim Classic Sun Hat - Sun 'N' Sand Hats

    $ 31.00

    Embrace timeless elegance with this iconic French breton-inspired sun hat, designed for the modern traveler who refuses to compromise on style or p...

    View full details
    $ 31.00
  • Savannah Visor by Wallaroo Hats Visor Cap Wallaroo Hats
    Savannah Visor by Wallaroo Hats Visor Cap Wallaroo Hats

    Savannah Visor by Wallaroo Hats

    $ 49.00

    The Savannah Visor delivers the elegance of the classic designer striped Savannah hat in a breezy, open-top visor style. Its wide brim offers excel...

    View full details
    $ 49.00
  • Butterfly Split Brim Sun Hat with Straw Bow - Boardwalk Style Wide Brim Hat Boardwalk Style Hats
    Butterfly Split Brim Sun Hat with Straw Bow - Boardwalk Style Wide Brim Hat Boardwalk Style Hats

    Butterfly Split Brim Sun Hat with Straw Bow - Boardwalk Style

    $ 27.00

    Turn heads while staying protected in the Butterfly Split Brim Sun Hat, designed by Boardwalk Style Hat Company with feminine detail. Featuring a u...

    View full details
    $ 27.00
  • Summer Cloche with Gold Chain Link Band and Scarf Cloche Something Special LA htp666fc Fuchsia Medium (57 cm)
    Summer Cloche with Gold Chain Link Band and Scarf Cloche Something Special LA htp666nv Navy Medium (57 cm)

    Summer Cloche with Gold Chain Link Band and Scarf

    $ 18.00

    Asymmetrical bonnet like hat. Sheer scarf looped through gold color chain links. Bow in back. Down sloping 4" wide band, disappears toward back. Ad...

    View full details
    $ 18.00
  • Soft Knit Wool Cloche Hat with Rolled Edge - Adora Wool Hat® Cloche Adora Hats AD1063C Sand Medium (57.5 cm)
    Soft Knit Wool Cloche Hat with Rolled Edge - Adora Wool Hat® Cloche Adora Hats AD1063B Ivory Medium (57.5 cm)

    Soft Knit Wool Cloche Hat with Rolled Edge - Adora Wool Hat®

    $ 31.25

    Discover timeless elegance with this charming wool cloche hat, featuring a graceful dome crown and plush rolled brim that frames your face beautifu...

    View full details
    $ 31.25
  • Supplex Dimensional Brim Hat, Slate - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co. MC288SLATE1 Slate S/M (56 cm)
    Supplex Dimensional Brim Hat, Slate - DPC Outdoor Headwear Bucket Hat Dorfman Hat Co.

    Supplex Dimensional Brim Hat, Slate - DPC Outdoor Headwear

    $ 32.00

    Step into the outdoors with unwavering confidence wearing this Supplex Dimensional Brim Hat. Crafted from premium Supplex® nylon, this hat combines...

    View full details
    $ 32.00
  • Asymmetrical Brim Sun Hat with Chiffon Sash - Sun 'N' Sand Hat Wide Brim Hat Sun N Sand Hats HH1797C Black Medium (57 cm)
    Asymmetrical Brim Sun Hat with Chiffon Sash - Sun 'N' Sand Hat Wide Brim Hat Sun N Sand Hats HH1797B Tan Tweed Medium (57 cm)

    Asymmetrical Brim Sun Hat with Chiffon Sash - Sun 'N' Sand Hat

    $ 31.00

    Turn heads wherever your adventures take you with this distinctive asymmetrical sun hat. The uniquely tapered brim offers 4 inches of coverage in f...

    View full details
    $ 31.00
  • Wide Brim Braided Floppy Beach Hat for Large Heads - Fadivo Hats Wide Brim Sun Hat Fadivo New York
    Wide Brim Braided Floppy Beach Hat for Large Heads - Fadivo Hats Wide Brim Sun Hat Fadivo New York CH4510-BLK Black Large (58.5 cm)
    Sale

    Wide Brim Braided Floppy Beach Hat for Large Heads - Fadivo Hats

    Original Price $ 27.00
    Current Price $ 20.00

    Stay stylishly shaded with this wide-brim beach hat crafted from wide toyo straw braids for lightweight comfort and standout summer style. Designed...

    View full details
    Original Price $ 27.00
    Current Price $ 20.00
    Sale

Adjustable hats make it easy to perfect your fit—whether you’re between sizes, sharing a hat, traveling, or simply want a more secure feel on windy days. A better fit doesn’t just feel more comfortable; it also helps your hat stay in place and sit correctly for the coverage you’re counting on.

There are several smart ways hats are made adjustable, including: an interior drawstring inside the sweatband, an elasticized strap with a buckle hidden inside the inner band, an elastic back band with a toggle lock, a classic Velcro® closure, a strap closure with a T-slide, or a small hook-and-loop closure tucked under the sweatband. These built-in systems let you fine-tune the circumference without sacrificing style—so your hat feels snug, secure, and made for you.