Janessa Leoné Sherman Hat

From countryside to cityscapes, the Tessa transitions seamlessly. We’ve updated the on-trend fedora silhouette with a slightly floppy brim and soft wool felt that provides comfortable warmth and easy packability. The internal sizing system ensures a dreamy fit. Dresses up with long skirts and boots, dresses down with puffy vests and…

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Make a statement with the Lauren fedora, a bold blend of contrasting colors and a chic, feminine design. Crafted from our exclusive Flexi-Weave fabric, this UPF 50+ lightweight and durable hat is perfect for travel—whether you're jet-setting to tropical beaches, exploring vibrant cities, or attending outdoor events. Stylish and versatile, the Lauren is your go-to accessory for turning heads wherever your adventures take you.

by Wallaroo Hat Company · Boulder, Colorado

🚚 Ships from Colorado

Add a breezy vibe to your next summer day outing with our grass woven fedora. Color: Black or Natural Size: Small/Medium 57cm Crown: 12cm Brim: 9.5 Woven Grass Knotted brown leather band or natural leather cord.

by Made X Hudson · Hudson, NY

🚚 Ships from New York

Elevate your summer with the Tully, a relaxed take on our fedora with an open weave and frayed brim. This hat is begging to go to the beach, worn in a partially shaded garden, or with a sun dress on your way to a patio dinner. The interior band has an adjustable cord inside for finding your best fit. Natural straw color with a leather knotted band detail Wove n seagrass S/M Crown: 4", brim: 4"

by Made X Hudson · Hudson, NY

🚚 Ships from New York

Say hello to the Miller Fedora Hat—a sharp, modern update on a true classic. With its tall, defined pinched crown and structured wide, flat brim, Miller delivers timeless fedora style with a fresh, elevated edge. Clean lines and bold proportions make it a standout staple for any wardrobe—easy to dress up, tone down, or personalize to your vibe. Finished with a hand-sewn suede band, it layers effortlessly with your favorite hat accessories for endless styling options.

by Gigi Pip · Utah

🚚 Ships from Utah

The Charlie Fedora seamlessly blends sophisticated styling with contrast stitching for a timeless look. Perfect for urban exploration, waterfront strolls, or outdoor adventures, its neutral tones exude a light, airy elegance that pairs effortlessly with any outfit. Packable and versatile, this UPF 50+ fedora is designed for easy travel and is ready to elevate your style wherever you go.

by Wallaroo Hat Company · Boulder, Colorado

🚚 Ships from Colorado

Beach hat or fedora? Now you don’t have to choose! The Coronado is a floppy-brimmed fedora that follows anywhere you go. The fabric blend makes for warm weather comfort and easy packability. Decorative leatherette hatband dresses you up for the links or a late brunch.

Enhance your style with this chic fedora, featuring an elegant feminine bow trim for a timeless touch. Designed with a 4" wide brim, it provides exceptional UPF 50+ sun protection, letting you step out with confidence. Crafted from travel-friendly Flexi-Weave material, this versatile and comfortable hat is perfect for a day out in the sun or exploring the town.

by Wallaroo Hat Company · Boulder, Colorado

🚚 Ships from Colorado

The traditional fedora silhouette gets a modern update with trendy boho-chic styling. The soft felt finish makes it the perfect UPF 50+ hat for year-round wear.

by Wallaroo Hat Company · Boulder, Colorado

🚚 Ships from Colorado

Try something flashy vintage simple classic Fedora Hat. These are even better by the adjustable drawstring and the breathable, unlined interior. DIMENSION: Height: 4.75" Brim: 2.75" Circumference: 22" Material: 65% cotton, 35%…

by Key Bliss Boutique · Grand Forks, ND

🚚 Ships from North Dakota

Meet the Shiloh Tall Fedora Hat—a sleek, structured staple designed for elevated everyday wear. Featuring a tall classic fedora crown and a stiff flat brim, Shiloh offers a flattering silhouette that adds instant polish to any outfit. The tonal nude leather band adds subtle texture and a refined finish, making it easy to style across seasons and wardrobes. Lightweight yet durable, this hat holds its shape beautifully while offering all-day comfort. Whether you're dressing it up or pairing it with casual looks, Shiloh brings effortless style and confident structure to your day.

by Gigi Pip · Utah

🚚 Ships from Utah

The San Cristobal Fedora is our bestselling woven summer hat, loved for its timeless shape, lightly structured crown, and signature medium brim. Handwoven from natural palm straw, it's the kind of piece you'll reach for season after season—whether you're headed to the beach, exploring a new city, or enjoying a slow afternoon outdoors. Designed to adapt to the way you wear it, the San Cristobal features a removable genuine leather hatband and our signature Interchangeable Styling System.

by Redemption Market · Phoenix, AZ

🚚 Ships from Arizona

Shannon Tennis Socks in Optic White from Tanya Taylor. Step into the Off Court spirit with the Shannon Tennis Socks, featuring our interwoven tennis racquet logo for a sporty and preppy look. Soft, breathable, and effortlessly polished, they bring classic court style to your everyday rotation.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

The Gretchen Skirt in Tawny Brown from Xirena. Flower Power. Gretchen is made in Xirena's floral print viscose chiffon. This flowy bohemian midi skirt is lined and features an elasticized waist and asymmetrical tiered ruffles.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

The Draper Pant in Dark Seagrass from Xirena. Easy does it . Draper is made in our classic lightweight woven cotton poplin for a lived-in look and feel. Draper is an easy pull-on pant with a drawstring waist and side seam pockets.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

The Organized Chaos Note Pad in Cognac from Sloane Stationery. A chic pocket journal with "Organised Chaos" embossed on the faux lizard cover. Gold edges, grosgrain ribbon page marker; plain paper inside.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

Double-Breasted Stretch-Wool Crop Blazer in Rl Navy from Ralph Lauren. Tailored with Italian stretch wool faille, this blazer has a slightly cropped, double-breasted silhouette with signature helmet-and-mallet–engraved metal buttons.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

The Mini Puffy in Red from Jorja. The Puffy, but miniature. She's the perfect night out bag, and she's equally perfect for city saunters, the errand or other daytime adventures. She's everything you need.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

The Boy Blazer in Rosen from TWP. Oversized, one-button blazer tailored in chintzed linen. Fabric is a classic, compact linen with a chintzed finish for structure and a subtle, luxe sheen. The Boy Blazer is tailored with a peaked lapel and custom molded shoulder pads. Complete with side pockets, chest welt pocket and back vent.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

The Wild Rag in Navy/Camel from Guest in Residence. The Wild Rag is a Guest in Residence icon — a cotton-silk bandana finished in their reversible paisley jacquard. Effortlessly soft and endlessly versatile, it’s the best-selling scarf that completes every look.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

The Iconic Flag Sweater (Kids) from Ralph Lauren. Knit with soft cotton yarns, The Iconic Flag Sweater reflects Ralph Lauren’s long-standing love of American style. It is detailed with 13 embroidered stars inspired by early American flags.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut

Coco Dress in Maritime Blue from Tanya Taylor. Effortless and sporty, the Coco Dress brings the Off Court spirit to everyday dressing. Crafted for movement and comfort, Coco features a sleek silhouette, contrasting trim, and a subtle tennis logo for a nod to classic court style. Lightweight and breathable, it transitions seamlessly from matches to city afternoons.

by Pinnacle · Washington Depot, CT

🚚 Ships from Connecticut