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        Home / Small Batch Collection / Bennett Winch Leather Weekender

        Bennett Winch Leather Weekender

        Bennett Winch

        $2,950

        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender
        Bennett Winch Leather Weekender

        Bennett Winch Leather Weekender

        Bennett Winch

        $2,950

        Color: Black
        Size

        This style is excluded from promotion

        A luxurious, handcrafted travel bag made in England from premium full-grain vegetable-tanned leather. Designed to age beautifully and last a lifetime, it combines timeless style with exceptional functionality. With a fully protected 16" laptop sleeve, concealed passport pocket, internal tech compartment, and dual waterproof sections—including a separate shoe compartment—it’s built to serve the needs of the modern traveler. IATA carry-on compliant with a 42L capacity, it's the perfect companion for journeys near and far.

        • Full grain veg-tanned leather, solid brass hardware, cotton lining, YKK golden brass zips
        • 55cm L x 36cm W x 25cm H
        • Made in England
        • To clean, gently wipe with a soft cloth and apply leather cream as needed.
        • Style WKD-LEA

        DESIGN: Color-blocked tipping at the trim gives this polo a vintage-meets-modern touch.

        FABRIC: This cotton-cashmere yarn is breathable and luxuriously soft (perfect for wearing winter to spring).

        HOW TO WEAR IT: This versatile sweater polo is dressier than a tee but can be styled up or down just as easily.

        DESIGN: Comfortable, structured, and cut with a classic crewneck collar and an easy, flattering fit.

        FABRIC: Our soft and sturdy Premium Jersey is made from piece-dyed and garment-washed Portuguese cotton.

        HOW TO WEAR IT: A year-round staple. Slim enough to wear as a base layer but solid enough to wear solo.

        DESIGN: Classic 5-pocket styling — belt loops, zip fly, rivets — and two fits make these an easy bestseller.

        FABRIC: This stretch twill is made from a garment-dyed cotton blend with a comfortable, lived-in look and feel.

        HOW TO WEAR IT: Rugged denim styling and an elevated fabric make these the perfect everyday pants.

        DESIGN: The first button-down collars kept 19th-century English polo players’ collars from flapping in the wind.

        FABRIC: Oxford cloth is a dense cotton fabric; ours is woven in Japan on vintage looms, with a selvedge finish.

        HOW TO WEAR IT: Tucked or not, buttoned or open; the Oxford’s casual-meets-formal vibe works with everything.

        DESIGN: The vintage-inspired details, like oxidized rivets and a shank fly, are pulled from Todd’s favorite jeans.

        FABRIC: Identified by its red interior seams, our small-batch selvedge denim is woven on vintage looms.

        HOW TO WEAR IT: A Goldilocks fit, with a mid-rise and classic straight leg, these are easy to wear with anything.

        DESIGN: Todd’s luxe update on the iconic trucker features two chest pockets and adjustable tabs at the waist.

        FABRIC: Our premium Italian calf suede is made in Tuscany, Italy, by the leather masters at Pellemoda.

        HOW TO WEAR IT: A timeless statement piece, our bestselling Dylan instantly elevates even a tee and jeans.

        DESIGN: A half-cardigan stitch in the body and ribbed trim give this classic crew a subtly rugged look and feel.

        FABRIC: Our 3-season Beechwood yarn is specially spun from organic cotton to stay light and hold its shape.

        HOW TO WEAR IT: Breathable and classic, this sweater is made for comfortable, easy layering at work or home.

        DESIGN: The adjustable side tabs at either side of the waist are a detail borrowed from bespoke tailoring.

        FABRIC: This Italian linen blend is lightweight, breathable, and specially treated to resist wrinkling.

        HOW TO WEAR IT: With no need for a belt, these trousers look extra clean with a tucked-in shirt.

        DESIGN: This softly structured sport coat has a natural shoulder, without any bulky padding.

        FABRIC: Strong, breathable and wrinkle-resistant, cotton pique is a sophisticated choice for warm weather.

        HOW TO WEAR IT: Universally flattering, this relaxed take on a classic blazer can dress up any look.

        DESIGN: Classic athletic details, like raglan sleeves, meet a chest pocket — Todd’s nod to the iconic Oxford shirt.

        FABRIC: Our Portuguese cotton terry is 380 grams per square meter, an ideal weight for three-season wear.

        HOW TO WEAR IT: With a flattering fit and solid-yet-soft handfeel, this looks just as good with trousers as sweats.

        DESIGN: Rows of subtle cable stitches add visual texture to the front of this polo for an elevated look.

        FABRIC: This is a soft, lightweight cotton jacquard, where the cable pattern is woven directly into the fabric.

        HOW TO WEAR IT: A dressed-up take on a classic knit polo, it looks great with denim or tucked into trousers.

        DESIGN: Traditional details — a yoke, chest pockets, and snaps — give this refined shirt a little rugged flair.

        FABRIC: A special finish and cold wash prevent shrinkage and break in stiff fibers for a soft, airy feel and clean look.

        HOW TO WEAR IT: Try it as a rugged swap to a classic point collar, or wear it open as a light layer.

        DESIGN: The adjustable, self-belted waist, meant to sit slightly high, is inspired by a vintage British military style.

        FABRIC: Soft but crisp, naturally cooling, designed to rumple beautifully — linen is made for warm weather.

        HOW TO WEAR IT: The Gurkha’s clean lines (no belt required) and structure instantly dresses up any outfit.

        DESIGN: With a wide, tapered placket and chunky rib stitch, this polo is a masterclass in minimalism.

        FABRIC: A blend of breathable cotton and luxuriously soft cashmere that’s excellent for between season wear.

        HOW TO WEAR IT: Dressier than a tee and just as comfortable; try it solo or layered under jackets.

        DESIGN: Point collars popped up on mid-century shirting, and add a traditional look that grounds the ease of linen.

        FABRIC: A special finish and cold wash prevent shrinkage and break in stiff fibers for a soft, airy feel and clean look.

        HOW TO WEAR IT: Buttoned or open, with everything from suits to shorts; the most versatile shirt in your closet.

        DESIGN: A straight fit, concealable drawstring, and camp pockets give these laidback pants extra style.

        FABRIC: Breathable, soft, and naturally cooling, this linen is piece-dyed for even color.

        HOW TO WEAR IT: Dress them up or down; pull-on ease meets refined linen for peak versatility.

        DESIGN: A classic fit, side seam vents, a chest pocket and cover stitching give this tee a clean look.

        FABRIC: Made from flax, the Portuguese linen in our t-shirts has a dry feel and is naturally cooling.

        HOW TO WEAR IT: More refined than jersey, this tee elevates any outfit, worn layered or solo.

        DESIGN: Tailored pleats and belt loops meet an elastic drawstring waist for the best of both worlds.

        FABRIC: Soft, refined, breathable, linen — made from flax — is the cashmere of summer.

        HOW TO WEAR IT: Dress these down with a tee and sandals, or up with a polo and loafers.

        DESIGN: Our traditional chore has an easy fit, horn buttons at the placket and cuffs, and patch pockets.

        FABRIC: Sturdy and soft, this linen is breathable enough for hot days but still rugged.

        HOW TO WEAR IT: The ideal lightweight layer to finish any look (and perfect for packing on a trip).

        DESIGN: Our Madison Jacket has natural shoulders and a peak lapel with pick-stitching for an artisan look.

        FABRIC: This lightweight linen-cotton, woven in Italy, has a subtle, elevated nailhead texture.

        HOW TO WEAR IT: Wear the full Madison suit for formal occasions, or break it up with denim.

        DESIGN: Our bestselling Montauk Polos can be spotted by their button-less collars, which give a clean look.

        FABRIC: A soft blend of breathable linen and wrinkle-resistant cotton in a subtle rib stitch.

        HOW TO WEAR IT: An all-occasion pick that’s easier than a shirt and more elevated than a tee.

        Runway Collection:
         La Buena Vida | Vintage Style

        Todd’s Spring/Summer 26 runway collection balances structured tailoring and soft sensuality, inspired by the faded glamour of Havana in the 50s and the swagger of a guy stepping off a plane in Miami in the 80s.

        The sweaters in La Buena Vida are all inspired by mid-century styles, layering in different old-school details: an extra tab closure at the hem, tapered waists, extended collars, vintage-inspired patterns, and more.

        Runway Collection:
         La Buena Vida | Quality Fabrics

        Todd’s Spring/Summer 26 runway collection balances structured tailoring and soft sensuality, inspired by the faded glamour of Havana in the 50s and the swagger of a guy stepping off a plane in Miami in the 80s. 

        The shirts in La Buena Vida are crafted from carefully sourced fabrics, woven using heritage techniques at some of the world’s finest mills (like delicate voile, made from cotton, linen, and ramie and woven in Italy and India) and feature embroidered details.

        Runway Collection:
         La Buena Vida | Expert Tailoring

        Todd’s Spring/Summer 26 runway collection balances structured tailoring and soft sensuality, inspired by the faded glamour of Havana in the 50s and the swagger of a guy stepping off a plane in Miami in the 80s. 

        The jackets, trousers and suits in La Buena Vida reimagined old-school styles in streamlined, modern silhouettes, pairing laidback ease with sharp lines.

        Behind the Seams: Pellemoda

        Pellemoda has been making luxury suede and leather garments for 40 years. Everything happens under one roof, from sourcing and pattern-making to dyeing, cutting and sewing. View the story

        Shop All Pellemoda
        Behind the Seams: Pantex

        This family-owned business just west of Florence is responsible for the soft tweeds in our jackets and suits. View the Story

        Shop All Pantex
        Behind the Seams: Lyria

        This family-owned business in Prato weaves the fabrics for our Collection outerwear and shirting. View the story

        Shop all Lyria
        Behind the Seams: Bellandi

        This family-owned mill is committed to preserving Italy's heritage wool traditions. View the story

        Shop all Bellandi