Hobo Small
Effortless by Design
4 interest-free payments of
$74 with . Learn More
The leather bag that goes from morning errands to evening plans.
Best for: Errands Dinners Weekends
Hobo Small
Effortless by Design
Loved by professional women
2 Year Warranty
Free US Shipping
LIMITED QUANTITIES · EXPECTED TO SELL OUT
The polished hobo silhouette you love — finally built to keep up. Soft, full-grain pebbled leather that only gets better with time. Fits your iPad, wallet, and essentials without the bulk — just 1.25 lbs of effortless style. From brunch to errands to dinner, this is the bag you'll grab on your way out the door.
The relaxed hobo silhouette you love—finally built to keep up. Unlike most hobos that are just one big open space, ours is fully zipped and thoughtfully organized, with a padded iPad sleeve, tech and zip pockets, and structured holders for your water bottle or umbrella (yes, even a Stanley). Soft, full-grain pebbled leather keeps it polished yet durable, with a strap that works on the shoulder or hands-free. Effortless on the outside. Seriously functional on the inside.
11" iPad
Fits your stanley
just 1.25 lbs
Built-in key leash
Shoulder or Crossbody
4 Interior Pockets
Why the Hobo
- Fits up to an 11" iPad Air and Mini in a padded sleeve
- Structured interior prevents sagging, even when fully packed
- Elegant enough for meetings, practical enough for travel
- Secure top zipper—uncommon in hobo bags
- Comfortable shoulder or messenger carry
Design & Materials
- Full-grain pebbled leather with a soft, durable hand feel
- Water-resistant signature lining
- Adjustable long strap for shoulder or crossbody wear
- Structured silhouette with a soft drape for balanced comfort
- 7 liters
- 12" L x 10" H x 4" D
- Adjustable strap drop 9"-12"
Ideal For
- Work and office days
- Daily commuting
- Travel personal item
Interior Organization
- Padded sleeve for iPads and Kindles 11"
- Three interior pockets: two slip, one zip
- Two vertical holders for water bottle or umbrella (one Stanley-coffee cup)
- Pen loops and integrated key leash
Shipping & Return Policy
Shipping: We offer free U.S. shipping on all orders over $200. Free shipping is automatically applied at checkout when your order meets the minimum.
Returns: Indulge in a worry-free experience. You have 14 days from the time of delivery to decide if it’s truly meant for you. If it’s perfect, enjoy it. If not, simply return it, ensuring the item remains unused and the wheels untouched by the journey.
The relaxed hobo silhouette you love—finally built to keep up. Unlike most hobos that are just one big open space, ours is fully zipped and thoughtfully organized, with a padded iPad sleeve, tech and zip pockets, and structured holders for your water bottle or umbrella (yes, even a Stanley). Soft, full-grain pebbled leather keeps it polished yet durable, with a strap that works on the shoulder or hands-free. Effortless on the outside. Seriously functional on the inside.
Details
Premium full-grain leather
Meets carry-on regulations
Fits up to a 16" Macbook Pro
Water-resistant lining
H: 10” (25 cm) W: 12” (30 cm) L: 21” (53 cm)
Leather Weight: 7 lbs (3 kg)
48 L capacity
Garment bag size: 48" Long x 22" wide
Materials
Premium full-grain pebbled leather
Water-resistant lining
High-end YKK zippers
Aviation-grade aluminum trolley
Leather handle on trolley
High-performance wheels
Care Advice
To care for the Nova, regularly clean it with a soft, damp cloth and condition it with a suitable leather conditioner to keep it supple and prevent cracking.
Choose options
Hobo Small
Effortless by Design
Loved by professional women
2 Year Warranty
Free US Shipping
LIMITED QUANTITIES · EXPECTED TO SELL OUT
The polished hobo silhouette you love — finally built to keep up. Soft, full-grain pebbled leather that only gets better with time. Fits your iPad, wallet, and essentials without the bulk — just 1.25 lbs of effortless style. From brunch to errands to dinner, this is the bag you'll grab on your way out the door.
The relaxed hobo silhouette you love—finally built to keep up. Unlike most hobos that are just one big open space, ours is fully zipped and thoughtfully organized, with a padded iPad sleeve, tech and zip pockets, and structured holders for your water bottle or umbrella (yes, even a Stanley). Soft, full-grain pebbled leather keeps it polished yet durable, with a strap that works on the shoulder or hands-free. Effortless on the outside. Seriously functional on the inside.
Details
Premium full-grain leather
Meets carry-on regulations
Fits up to a 16" Macbook Pro
Water-resistant lining
H: 10” (25 cm) W: 12” (30 cm) L: 21” (53 cm)
Leather Weight: 7 lbs (3 kg)
48 L capacity
Garment bag size: 48" Long x 22" wide
Materials
Premium full-grain pebbled leather
Water-resistant lining
High-end YKK zippers
Aviation-grade aluminum trolley
Leather handle on trolley
High-performance wheels
Care Advice
To care for the Nova, regularly clean it with a soft, damp cloth and condition it with a suitable leather conditioner to keep it supple and prevent cracking.
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.
Send a message Close
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.
Secure Payment
Shop with confidence! Our secure payment methods and shiny SSL certificates protect your financial info like a VIP bouncer—safe, secure, and stylish.
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