Does the Hobo Medium fit a 16" laptop?

No. The Medium is built for 14" laptops and under. If you carry a 16" MacBook Pro, the Hobo Large is the right fit for you.

Is the Hobo Medium big enough for a full work day?

Yes — that's exactly what it's designed for. It fits your 14" laptop, charger, wallet, keys, and a water bottle with room to spare. If you also need to pack gym clothes or a change of shoes, go with the Large.

Does the Hobo Large have feet or studs on the bottom?

No. We chose not to add feet because the Hobo is meant to feel soft, light, and mobile — not structured like a briefcase. It's built for daily use, not table display.

Can the Hobo Large be worn crossbody?

Yes. The strap is fully adjustable — wear it short as a handbag, or extend it to the maximum length for crossbody wear.

What's the width of the Hobo Large?

The bottom of the bag is 16.5" wide. The top tapers slightly, which is what creates the hobo silhouette.

How much does the Hobo Large weigh?

2 lbs — designed to feel light in the hand and on the shoulder throughout the day.

Packing of the Large Hobo

The Hobo

Made to carry your whole day.

One silhouette, three sizes, full-grain leather — built to go everywhere you do.

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Best Women's Hobo Bag | #Color_Chocolate

The Hobo

Made to carry your whole day.

One silhouette, three sizes, full-grain leather. Find the Hobo that fits your life.

★★★★★ 4.8 · 412 reviews

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Color

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See how each size wears.

All three sizes on the same model — find your fit.

Model is 5'9"

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Best Match

4.9

Rated 4.9 out of 5 stars

31 Reviews

Hobo Large

Travel & Long Work Days

TravelLong work daysOvernight

16" Laptop Laptop

2 lbs Weight

16.5 L Capacity

What Fits Inside

16" MacBook Pro
Charger
Notebook
Gym clothes
Water bottle

"I carry my MacBook Pro, charger, notebook, and gym clothes — this bag handles my whole day."

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Best MatchMost Popular

Just Launched

Hobo Medium

The Everyday Workhorse

Daily commuteOfficeErrands

14" Laptop Laptop

1.75 lbs Weight

13 L Capacity

What Fits Inside

14" MacBook
Charger
Wallet
Keys
Water bottle

"I go from meetings to coffee to errands — it fits my laptop and essentials without feeling bulky."

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Best Match

Just Launched

Hobo Small

Minimal & Stylish

ErrandsDinnersWeekends

iPad Laptop

1.5 lbs Weight

10 L Capacity

What Fits Inside

iPad
Wallet
Keys
Sunglasses
Phone

"I want a polished bag for my iPad, wallet, and sunglasses — nothing more, nothing less."

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	Hobo Large	Hobo Medium	Hobo Small
Fits Laptop	16" MacBook Pro	14" MacBook	iPad
Weight	2 lbs	1.75 lbs	1.5 lbs
Pockets	6	5	4
Water Bottle	Yes (side pocket)	Yes (side pocket)	No
Key Leash	Yes	Yes	Yes
Best For	Travel & long days	Daily commute	Errands & dinners

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Hobo Medium in Sand

Hobo Small in Burgundy

Hobo Large in Chocolate

Hobo Medium in Jet Black

Does the Hobo Small fit a laptop?

No. The Hobo Small is designed for an iPad or tablet, wallet, and everyday essentials — not a laptop. If you need a laptop sleeve, the Hobo Medium (14") or Hobo Large (16") are better fits.

Is the Hobo Small too small for everyday use?

It depends on what "everyday" looks like for you. If your day is errands, coffee, dinner, and weekends — the Small handles it beautifully at just 1.25 lbs. If your day involves a laptop, charger, and notebook — go with the Medium or Large.

Can the Hobo Small be worn crossbody?

Yes. The strap is fully adjustable — wear it short on the shoulder or extend it for hands-free crossbody wear.

What's the difference between the three Hobo sizes?

The Small is built for minimalists — iPad, wallet, keys, sunglasses. The Medium adds a padded 14" laptop sleeve and more interior pockets for a full work day. The Large fits a 16" MacBook Pro plus charger, notebook, gym clothes, and a water bottle — it's built for travel and long days. All three share the same full-grain leather, adjustable strap, and key leash.

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Made to carry your whole day.

Made to carry your whole day.

See how each size wears.