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Crafted once. Carried for years.

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Hobo Large

$395
·

Boardroom to Boarding Gate

4.8
Rated 4.8 out of 5 stars
55 Reviews

4 interest-free payments of
$99 with . Learn More

Size
Small Fits iPad Large Fits 16" laptop

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

Best for: Work Commuting Daily Use

Hobo Large

Sale price$395

Boardroom to Boarding Gate

Size
Small Fits iPad Large Fits 16" laptop
4.8
Rated 4.8 out of 5 stars
55 Reviews
Sale price$395
Color:Burgundy
Airline Compatibility

Out of stock

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❤
Loved by professional women
✓
2 Year Warranty
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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.

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 2 lbs

Built-in key leash

Shoulder or Crossbody

4 Interior Pockets

COMPLETE WITH

#Color_Chocolate
$145
#Color_Chocolate
$145

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."

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?
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 55 reviews
98%would recommend this product
55 reviews
  • Bonnie
    Verified Buyer
    I recommend this product
    Rated 4 out of 5 stars
    4 days ago
    Incredibly large, beautiful leather!

    I got the large hobo in caramel and I do love it. I wanted something that would fit my giant water bottle, make up bag, other pouches, work laptop and my lunch. The leather is beautiful and rich and smells lovely. The shape of the bag is very cute, the large is a tank and can hold everything. My main gripe (and it’s not the bag’s fault) is the beautiful silhouette of the handle makes the opening quite small so unless you undo the strap so it can open wide (which they fairly show in the video), it is actually quite difficult to get a normal 14” laptop in and out of the sleeve, so it is not a speedy grab or stuff and go. The lining feels very heavy duty and feels like it will repel water well, but does feel a little cheap and plasticky, but I’ll trade the water repellence and ease of keeping clean with the crunchy plastic feel that I am hoping will soften with age. One last note, if you’re trying to get a laptop in and out without opening the strap, then it does push the zipper to the limit and it is a little tough getting it going again, but otherwise the zipper slides beautifully across the length. I am happy I purchased this bag and I did a lot of online research and chose this over bags twice its price because of the size and pockets and full zipper closure. Bag looks exactly as pictured and caramel color was true to the photos.

  • Amy C.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    2 weeks ago
    I thought it was too big

    I was a bit concerned initially that this bag was too big for me considering that im 4' 11". After using it for a few days I realized i love it! Great quality and even nicer after you break it in for a few days. Highly recommend

  • Chloe M.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    2 weeks ago
    Cute and functional

    All the right pockets and clips for a work bag. It looks nice and from what can tell the leather is a great quality too. Looks exactly as pictured

  • CHRISTINA S.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    2 weeks ago
    Really Good!

    Very happy with this bag. The large size is a bit big for day to day if you’re not using it for a commute. For me, it’s a great fit for a 16” laptop and work travel. I love the interior features, the adjustable strap, and I am pleased with the quality and style.

  • Denise M. O.
    Verified Buyer
    I recommend this product
    Rated 5 out of 5 stars
    2 weeks ago
    Fashionista Find

    I travel every month for work and wanted something functional and stand out fashionable!! This is it and my 16” laptop easily fits it without unfastening the handle. And it holds so much more!! Leather is beautiful and quality is superb!!