Hobo Small
$295Effortless by Design
The leather bag that goes from morning errands to evening plans.
Free Worldwide Shipping · 14-Day Returns
Color: Chocolate
The Hobo Small measures 12" × 10" × 4" (26 linear inches) — classified as a Personal Item (Under Seat).
| Airline | Personal Item (Under Seat) |
|---|---|
| Aegean Airlines | ✓ |
| Aer Lingus | ✓ |
| Air Canada | ✓ |
| Air France | ✓ |
| Air India | ✓ |
| Alaska Airlines | ✓ |
| Allegiant | ✓ |
| American Airlines | ✓ |
| Austrian Airlines | ✓ |
| British Airways | ✓ |
| Cathay Pacific | ✓ |
| Delta | ✓ |
| EasyJet | ✓ |
| Emirates | ✓ |
| Ethiopian Airlines | ✓ |
| Frontier | ✓ |
| Hawaiian Airlines | ✓ |
| Iberia | ✓ |
| Icelandair | ✓ |
| JetBlue | ✓ |
| KLM | ✓ |
| Korean Air | ✓ |
| Lufthansa | ✓ |
| Norwegian | ✓ |
| Qantas | ✓ |
| Qatar Airways | ✓ |
| Ryanair | ✓ |
| Scandinavian Airlines | ✓ |
| Singapore Airlines | ✓ |
| Southwest | ✓ |
| Spirit | ✓ |
| Sun Country | ✓ |
| Swiss | ✓ |
| TAP Air Portugal | ✓ |
| Turkish Airlines | ✓ |
| United | ✓ |
| Virgin Atlantic | ✓ |
| Vueling | ✓ |
| WestJet | ✓ |
Comparison based on published linear inch limits. Airlines with "~" are within 2 inches of the limit — soft-sided bags typically pass but rigid sizer enforcement may vary.
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Beautiful quality leather and just a class beautiful bag with great organization/pockets
— Kat G., Verified Buyer
Hobo Small · Chocolate · Full-Grain Leather
$295
Quick view
Wool & Oak
Hobo Small
Effortless by Design
The leather bag that goes from morning errands to evening plans.
Out of stock
Get notified when it's back
Email me when it's back in stock. You'll also hear about new releases.
Something went wrong. Please try again.
You're on the list. We'll email you when it's back.
See it on
See it on. See what fits.
Each size shown on a 5'9" model — so you can choose your size with confidence.
Model 5'9"Carrying the Small
Model 5'9"Carrying the Large
Minimal & stylish — the essentials, elevated.
- FitsiPad
- Weight1.25 lbs
- Capacity7 L
What fits inside
- iPad
- Wallet
- Keys
- Sunglasses
- Phone
Travel & long work days.
- Fits16" laptop
- Weight2 lbs
- Capacity16.5 L
What fits inside
- 16" MacBook Pro
- Charger
- Notebook
- Gym clothes
- Water bottle
The Hobo Collection
Find Your Perfect Hobo
Hobo Large
Travel & Long Work Days
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."
Just Launched
Hobo Small
Minimal & Stylish
What Fits Inside
- iPad
- Wallet
- Keys
- Sunglasses
- Phone
"I want a polished bag for my iPad, wallet, and sunglasses — nothing more, nothing less."
FAQ
Questions & Answers
Does the Hobo Small fit a laptop?
Is the Hobo Small too small for everyday use?
Can the Hobo Small be worn crossbody?
What's the difference between the three Hobo sizes?
Still have questions?
We usually respond within 24 hours.
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The Wool & Oak Difference
Quality Craftsmanship
Our collection is rigorously tested and personally used by us. We choose only the finest leathers and hardware, crafted by expert artisans in India. Perfect for our adventures—and yours!
Easy Returns
Return items within 14 days for a full refund. We'll email a prepaid shipping label—just print and ship.
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