Hobo Medium
From Desk to Everywhere
4 interest-free payments of
$86 with . Learn More
The leather bag that handles your whole day without slowing you down.
Best for: Commuting Office Errands
Hobo Medium
From Desk to Everywhere
Loved by professional women
2 Year Warranty
Free US Shipping
LIMITED QUANTITIES · EXPECTED TO SELL OUT
The everyday bag that actually keeps up. Full-grain pebbled leather with a padded 14" laptop sleeve, organized pockets for everything you need, and nothing you don't — all at just 1.75 lbs. From morning meetings to afternoon errands, this is the bag that works as hard as you do.
The everyday bag that actually keeps up. Full-grain pebbled leather with a padded 14" laptop sleeve, organized pockets for everything you need, and nothing you don't — all at just 1.75 lbs. From morning meetings to afternoon errands, this is the bag that works as hard as you do.
14" Laptop
Fits your stanley
just 1.75 lbs
Built-in key leash
Shoulder or Crossbody
4 Interior Pockets
Why the Hobo
- Fits a 14” 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
- 14.5" L x 10" H x 4"D
- Min handle drop - 6"
- Max handle drop - 20"
- 11 liters
Ideal For
- Work and office days
- Daily commuting
- Travel personal item
- Overnight trips or wellness days
Interior Organization
- Padded sleeve for laptops up to 14”
- 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.
The everyday bag that actually keeps up. Full-grain pebbled leather with a padded 14" laptop sleeve, organized pockets for everything you need, and nothing you don't — all at just 1.75 lbs. From morning meetings to afternoon errands, this is the bag that works as hard as you do.
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.
Elige opciones
Hobo Medium
From Desk to Everywhere
Loved by professional women
2 Year Warranty
Free US Shipping
LIMITED QUANTITIES · EXPECTED TO SELL OUT
The everyday bag that actually keeps up. Full-grain pebbled leather with a padded 14" laptop sleeve, organized pockets for everything you need, and nothing you don't — all at just 1.75 lbs. From morning meetings to afternoon errands, this is the bag that works as hard as you do.
The everyday bag that actually keeps up. Full-grain pebbled leather with a padded 14" laptop sleeve, organized pockets for everything you need, and nothing you don't — all at just 1.75 lbs. From morning meetings to afternoon errands, this is the bag that works as hard as you do.
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 Medium
Model 5'9"Carrying the Large
Minimal & stylish — the essentials, elevated.
- FitsiPad
- Weight1.5 lbs
- Capacity10 L
What fits inside
- iPad
- Wallet
- Keys
- Sunglasses
- Phone
The everyday workhorse.
- Fits14" laptop
- Weight1.75 lbs
- Capacity13 L
What fits inside
- 14" MacBook
- Charger
- Wallet
- Keys
- Water bottle
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
- Extra Large Stanley Cup
- Notebook
- Gym clothes
- ChargerWater 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
- Standard Stanley Cup
- Wallet
- Keys
- Charger
"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
- Stanley Coffee Cup
- Keys
- Sunglasses
- Phone
"I want a polished bag for my iPad, wallet, and sunglasses — nothing more, nothing less."
FAQ
Questions & Answers
Does the Hobo Medium fit a 16" laptop?
What's the difference between the three Hobo sizes?
Can the Hobo Medium be worn crossbody?
Is the Hobo Medium big enough for a full work day?
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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