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Crafted once. Carried for years.

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Hobo Large

$395
4.8
Rated 4.8 out of 5 stars
65 Reviews

Boardroom to Boarding Gate

The leather work bag that goes from boardroom to boarding gate.

Hobo Large
At a glance
LaptopPadded 14" sleeve
Pockets4 interior
Key leashBuilt in
Dimensions16.5" L × 13" H × 4" D
Weight2 lbs
ShellFull-Grain Pebbled Leather

Free Worldwide Shipping · 14-Day Returns

Padded 14" Laptop Sleeve
4 Interior Pockets
Built-In Key Leash
16.5" L × 13" H × 4" DDimensions
2 lbsWeight
Full-Grain Pebbled LeatherShell

Color: Chocolate

Airline Compatibility

The Hobo Large measures 16.5" × 13" × 4" (33.5 linear inches) — classified as a Personal Item (Under Seat).

✓ Fits within limits ~ Tight — check with airline ✗ Exceeds limits
AirlinePersonal 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.

Order by 2pm ET · Ships today

Free Worldwide Shipping14-Day Returns4.6 on Trustpilot
“

Using this as a travel and diaper bag and it fits so much. I love the quality and the compartments inside are thoughtful.

— Benjamin S., Verified Buyer

Hobo Large · Chocolate · Full-Grain Leather

$395

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.

Small Hobo on a 5'9Small Hobo — what fits inside

Model 5'9"Carrying the Small

Large Hobo on a 5'9Large Hobo — what fits inside

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
Shop the Small — $295

Travel & long work days.

  • Fits16" laptop
  • Weight2 lbs
  • Capacity16.5 L

What fits inside

  • 16" MacBook Pro
  • Charger
  • Notebook
  • Gym clothes
  • Water bottle
Shop the Large — $395

The Hobo Collection

Find Your Perfect Hobo

You're ViewingMost Popular
Hobo Large

Hobo Large

Travel & Long Work Days

TravelLong work daysOvernight
16" LaptopLaptop
2 lbsWeight
16.5 LCapacity

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 Small

Just Launched

Hobo Small

Minimal & Stylish

ErrandsDinnersWeekends
iPadLaptop
1.25 lbsWeight
7 LCapacity

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

What is the holiday return policy?
Orders placed Nov 6 – Dec 31, 2026 can be returned until Jan 15, 2027.
Normal conditions apply: items must be unused, with original tags. A $14.95 return fee applies to continental US orders.
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.

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.

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.

4.8
Rated 4.8 out of 5 stars
Based on 65 reviews
95%would recommend this product
Slide 1 selected
65 reviews
  • Amanda
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    6 days ago
    The perfect travel bag

    I used my Wool & Oak large hobo for a work trip and absolutely loved it! It fits an incredible amount of stuff while still being convenient and easy to carry. What I particularly love is that it doesn’t look like a travel bag, so it transitions effortlessly from travelling to everyday use. It’s stylish, practical, and surprisingly spacious. I even had room to add an extra sweater in case the flight was cold. Exactly what I was looking for in a versatile bag that works just as well on a trip as it does day to day. Highly recommend!

  • Anja S.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    2 weeks ago
    Fits my whole life!

    I got this bag to use as I commute to and from grad school which ends up being about a 14 hour day many days of the week. It fits literally everything I need: 13 inch laptop, iPad, chargers, lunch, water bottle, ballet shoes and clothes, wipes, sweater, AirPods, lip balms and hair clips, sometimes my breakfast jar or coffee cup. The other day I fit my bike helmet in (I didn't have a lunchbox or clothes in there at the time, but everything else!). There is a clip for my keys and pockets for my sunglasses and badge. It is really good for keeping things organized compared to other bags I've used previously. I can fit my iPad in one of the zipper pockets to keep it separate from my laptop since I don't have either in a case and don't want them scraping. I use it crossbody when I'm biking around and it stays put and the strap is wide enough to keep from digging in too much. I shorten the strap and use it over my shoulder when I'm trying to be slightly more formal. The only thing I don't love is that things like lip balm and hair clips seem to disappear into the void of the zipper pockets since they're so deep and can get stuck under items in the bag. It would also be nice if there was one smaller zipper pocket near the top for the things I need to grab all the time, since the larger zipper pockets are so deep. The keychain is also a bit too long and I worry the key will fall into the laptop pocket and scrape up my laptop. Overall, I love this bag and my life is substantially…

  • Julie
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    3 days ago
    I love my new bag!

    I had been looking for a nice leather bag for work and I’m so glad that I found this one. It is exactly what I needed and fits everything I carry to work every day. The leather is really nice quality and I like all the pockets inside for organizing everything. The adjustable strap is great too.

  • Kayla H.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    4 days ago
    Beautiful!

    Room for everything and is gorgeous!

  • Sandra C.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    6 days ago
    Hobo is great

    Gift for my daughter, she loves it!