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Leather Hobo Bags

A hobo is the crescent-shaped bag that curves from a single strap and softens against your side. The Hollis keeps that slouch but adds a full zip top, so it holds a tablet, a layer and the daily kit without anything falling out.

Showing all 12 results

  • Black leather hobo bag, The Hollis, frontThe Hollis

    Black Leather Hobo Bag

    $185.00
    • Full-grain leather, cut and stitched by hand in our own workshop
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Black suede hobo bag, The Hollis, frontThe Hollis

    Black Suede Hobo Bag

    $195.00
    • Soft cow suede with full-grain leather trim, stitched by hand
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free on the leather trim
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Cognac leather hobo bag, The Hollis, frontThe Hollis

    Cognac Leather Hobo Bag

    $185.00
    • Full-grain leather, cut and stitched by hand in our own workshop
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Chocolate suede hobo bag, The Hollis, frontThe Hollis

    Chocolate Suede Hobo Bag

    $195.00
    • Soft cow suede with full-grain leather trim, stitched by hand
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free on the leather trim
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Tan leather hobo bag, The Hollis, frontThe Hollis

    Tan Leather Hobo Bag

    $185.00
    • Full-grain leather, cut and stitched by hand in our own workshop
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Tobacco suede hobo bag, The Hollis, frontThe Hollis

    Tobacco Suede Hobo Bag

    $195.00
    • Soft cow suede with full-grain leather trim, stitched by hand
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free on the leather trim
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Chocolate leather hobo bag, The Hollis, frontThe Hollis

    Chocolate Leather Hobo Bag

    $185.00
    • Full-grain leather, cut and stitched by hand in our own workshop
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Taupe suede hobo bag, The Hollis, frontThe Hollis

    Taupe Suede Hobo Bag

    $195.00
    • Soft cow suede with full-grain leather trim, stitched by hand
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free on the leather trim
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Oat leather hobo bag, The Hollis, frontThe Hollis

    Oat Leather Hobo Bag

    $185.00
    • Full-grain leather, cut and stitched by hand in our own workshop
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Moss suede hobo bag, The Hollis, frontThe Hollis

    Moss Suede Hobo Bag

    $195.00
    • Soft cow suede with full-grain leather trim, stitched by hand
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free on the leather trim
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Olive leather hobo bag, The Hollis, frontThe Hollis

    Olive Leather Hobo Bag

    $185.00
    • Full-grain leather, cut and stitched by hand in our own workshop
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free
    • Made to order, ships in 5 to 7 working days. 30 day returns
  • Oxblood suede hobo bag, The Hollis, frontThe Hollis

    Oxblood Suede Hobo Bag

    $195.00
    • Soft cow suede with full-grain leather trim, stitched by hand
    • 15.75″ W x 11.75″ H x 4.75″ D, 9.75″ drop
    • Up to a 13-inch tablet
    • Zip top, solid brass hardware
    • Three initials pressed free on the leather trim
    • Made to order, ships in 5 to 7 working days. 30 day returns

What makes a hobo a hobo

A hobo has three things: a crescent outline that dips in the middle, a single strap, and a body soft enough to slouch when you wear it. Many hobos leave the top open, which is the reason people stop carrying them. The Hollis closes with a full-width zip, so you keep the slouch and lose the worry.

Hobo vs tote vs shoulder bag

A tote has two handles and a fixed open shape. A shoulder bag is usually more structured. A hobo falls between the two: it holds roughly what a compact tote does, rides on one strap like a shoulder bag, and moulds to your side. It is the most forgiving shape for a bag that is overfilled on Monday and half empty by Friday.

Sizes in this collection

The Hollis measures 15.75 inches across and 11.75 inches tall when laid flat, but a hobo is never worn flat. On the shoulder it curves in by a couple of inches, which is why the 9.75-inch drop sits it comfortably under the arm.

StyleWidthHeightDepthDrop
Ashby shoulder12.5"9.5"4"9.5"
Hollis hobo15.75"11.75"4.75"9.75"
Selby slouchy16.25"11"4.25"10.75"
Kendal bucket9.75"9"4.75"11" + crossbody
Rydal satchel12.5"9"3.25"4" handle + long strap
Ripley saddle8.75"7.5"2.75"up to 22.75"
Tilly mini8.75"6.25"3.5"4" handle + crossbody
Mabel clutch11"7.5"0.75"wrist strap

The leather

A hobo only works if the leather is supple enough to curve without creasing hard. Full-grain with its surface intact bends into soft folds; cheaper corrected hides fold into sharp white lines along the crescent. That difference shows within weeks.

How it is made

The crescent is built from two curved panels joined by a gusset, stitched by hand so the seam follows the curve without puckering. The single strap is anchored at each horn of the crescent with doubled leather, because that is where a hobo carries its whole load.

Colours

On a hobo, colour shows off the folds. Cognac and tan pick up highlights along each curve as they age, black keeps the shape quiet and graphic, and oat makes the crescent read as a summer bag.

Initials, delivery and returns

The Hollis can carry three free initials near the zip end. It is cut when you order and ships in 5 to 7 working days, with 30 days to decide whether a hobo suits the way you carry.

Care

Because a hobo slumps when set down, store it stuffed with paper so the crescent keeps its line. Wipe the folds rather than scrubbing them, and condition it when the curves start to look dull.

How to style a hobo

Because it curves and softens, a hobo works best with relaxed clothes: knits, denim, linen, long coats. Worn high under the arm it looks neat. Let the strap out a little and it reads more bohemian. A dark Hollis with a long coat is the city version. Tan or oat with summer whites is the holiday one. Avoid packing a hobo with hard, square things like boxed chargers or books with sharp corners pressing out. Soft items let the crescent keep its shape, so put boxy things in a pouch.

What to put in a hobo, and what to leave out

A hobo works best with soft, mixed loads like a scarf, a cardigan, a bottle and a pouch of small items. It works less well with rigid square things that press against the curve, such as boxed chargers, hardback books and lunch boxes. Those make the crescent bulge and wear the leather unevenly. If you carry a tablet, slide it against the back panel, where the hobo is flattest. Keep keys clipped to the inside or in the zip pocket so they don't settle at the bottom of the curve.

Hobo bag sizes compared

Hobos usually come in three sizes. Small ones are about 11 to 12 inches wide and suit an evening or a light day. Medium ones, 14 to 16 inches, are the everyday size and hold a tablet. Large ones, 17 inches and up, are close to a tote. At 15.75 inches the Hollis is a medium, the size most people carry daily. If you want a smaller soft bag, the Tilly mini is the closest. If you need more room, our leather tote bags take a laptop.

Related collections

See also slouchy leather shoulder bags, leather shoulder bags or go back to all leather handbags.

Questions about leather hobo bags

Is a hobo bag good for everyday use?

Yes. A zipped hobo like the Hollis is one of the easiest daily bags because it fits a changing load and sits comfortably on one shoulder.

What fits in the Hollis hobo?

A tablet, a water bottle, a light layer, wallet, phone and keys.

Does the Hollis have a zip?

Yes, a full-width zip across the top, which many hobos lack.

Will the hobo lose its shape?

It is designed to soften, but the strap anchors are doubled so the horns of the crescent do not stretch.

Which colour hobo shows the patina most?

Cognac and tan, which pick up highlights along every fold.

Buying from us

No coated splits, anywhere

Nothing we sell is bonded, corrected or finished with a plastic film, which is what makes a cheap bag flake at the corners.

Full grain explained

Made to order

Cut when you order and dispatched in 5 to 7 working days, or 4 to 6 for the hand woven Wren. A monogram adds one working day.

Shipping and delivery

Your initials, at no cost

Three letters in gold foil, silver foil or a blind press, set by hand before the bag is boxed, on every bag we make.

Personalization

Made by people you can reach

If something is wrong, the reply comes from the workshop rather than a call center, and the repair is done by the person who made the bag.

Talk to us