Hobo Large
Boardroom to Boarding Gate
4 interest-free payments of
$99 with . Learn More
The leather work bag that goes from boardroom to boarding gate.
Best for: Work Commuting Daily Use
Hobo Large
Boardroom to Boarding Gate
Loved by professional women
2 Year Warranty
Free US Shipping
LIMITED QUANTITIES · EXPECTED TO SELL OUT
Finally, a work bag that does it all — without making you choose between style and function. Premium full-grain leather that develops a unique patina over time. Fits your 16" laptop, keeps everything organized, and weighs just 2 lbs. From boardroom to boarding gate, this is the bag you'll reach for every single day.
What they're saying
“Beautiful, functional, and all around perfect. My favorite everyday work bag.”
“Light and roomy. Stylish design and functional. Soft leather feels amazing.”
“Wanted it for over a year. Finally bought it — a very cool product.”
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 16” laptop 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.
16" Laptop
Fits your stanley
just 1.5 lbs
Built-in key leash
Shoulder or Crossbody
4 Interior Pockets
Pre-Order
Our most wanted bag, back August 14th. Last drop sold out in days — reserve yours now.
Why the Hobo
- Fits a 16” laptop 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
- 15 liters
- 16.5" L x 13" H x 4" D
- Min. strap length - 9"
- Max. strap length - 24.5"
Ideal For
- Work and office days
- Daily commuting
- Travel personal item
- Overnight trips or wellness days
Interior Organization
- Padded sleeve for laptops up to 16”
- Four interior pockets: two slip, two zip
- Two vertical holders for water bottle or umbrella (one Stanley-ready)
- Pen loops and integrated key leash
- Spacious main compartment for a cardigan, workout clothes, or travel essentials
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.
Pre-Order
Our most wanted bag, back August 14th. Last drop sold out in days — reserve yours now.
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 16” laptop 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 Large
Boardroom to Boarding Gate
Loved by professional women
2 Year Warranty
Free US Shipping
LIMITED QUANTITIES · EXPECTED TO SELL OUT
Finally, a work bag that does it all — without making you choose between style and function. Premium full-grain leather that develops a unique patina over time. Fits your 16" laptop, keeps everything organized, and weighs just 2 lbs. From boardroom to boarding gate, this is the bag you'll reach for every single day.
What they're saying
“Beautiful, functional, and all around perfect. My favorite everyday work bag.”
“Light and roomy. Stylish design and functional. Soft leather feels amazing.”
“Wanted it for over a year. Finally bought it — a very cool product.”
Pre-Order
Our most wanted bag, back August 14th. Last drop sold out in days — reserve yours now.
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 16” laptop 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.
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."
Hobo Medium
The Everyday Workhorse
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."
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."
Reasons to Love the Hobo
01 / 04
Made for Women Who Do It All
From client meetings to coffee runs to weekend getaways — the Hobo moves with you. Full-grain leather that only gets better with time, and a silhouette that never goes out of style.
02 / 04
Your Everyday Work Bag
Fits a 16” laptop in a padded sleeve, keeps four pockets organized, and still looks elegant walking into client meetings. From morning commute to after-work plans — one bag, zero compromises.
FAQ
Questions & Answers
Does the Hobo Large have feet or studs on the bottom?
Can the Hobo Large be worn crossbody?
What's the width of the Hobo Large?
How much does the Hobo Large weigh?
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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