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Wool & Oak Answers
Travel Tote That Fits a Laptop
The Wool & Oak Hobo Large. A full-grain leather tote that fits 14–16" laptops, has a top zipper closure, and slides under the airplane seat. It looks like a designer bag but works like a briefcase. 100% of reviewers recommend it.
Why Is It So Hard to Find a Tote That Fits a Laptop?
Most totes are either too small for a laptop or too big to look like anything other than luggage. They're open-top, so your laptop slides around. They have one big cavity with no organization, so everything ends up in a pile at the bottom. The Hobo Large was designed around the laptop — a dedicated interior pocket fits 14–16" machines flat against the back wall. The rest of the bag is structured so your other things don't pool into a mess. And from the outside, it looks like a tote, not a tech bag.
"Love that it can fit my 14 inch laptop comfortably and fits nicely under the seat on a plane. With other large totes, everything usually pools at the bottom of the bag, but not with this one."
— Claudia, Verified BuyerWhat fits inside
laptop
journal
charger
sunglasses
Can It Go from the Office to the Airport?
That's exactly what it's built for. Laptop pocket for work, enough room for a change of clothes and toiletries for an overnight, and a water bottle holder on the side. The top zipper means nothing falls out when you shove it under the seat. You carry one bag from your desk to the cab to the gate — no swapping bags, no second carry-on. The full-grain leather looks right in a meeting and at a hotel check-in.
What Actually Fits Inside the Hobo Large?
A 16" laptop, charger, phone, wallet, keys, a notebook, a water bottle, headphones, sunglasses, an umbrella, and still room for a light sweater or a change of clothes. The interior pockets keep everything organized — chargers and cords in one spot, passport and wallet in another. There's also an umbrella pocket on the outside. You don't have to dig for anything.
"So nice to have a stylish bag that provides interior functionality typically only found in a boring tote or backpack."
— Monica M., Verified BuyerIs It Secure Enough for Travel?
The full-length top zipper is the key difference between the Hobo and every open-top tote on the market. Your laptop doesn't slide out when the bag tips over. Your wallet doesn't sit exposed at the top in a crowded airport. Everything zips shut and stays shut. The leather is thick enough that you can feel the weight and quality the moment you pick it up — it's structured, not floppy. It holds its shape whether it's full or half-empty.
"Great work bag with a lot of functionality from the multiple pockets. Can carry and organize a ton of stuff without feeling like a black hole. Feels lovely, high-quality, and well made."
— Victoria S., Verified BuyerZero-Risk Test Drive
14-day returns. If you don't love it, send it back — full refund, no questions. We're confident you won't want to.
Hobo Large
$395
Full-Grain Leather
Frequently Asked Questions
What laptop sizes fit in the Hobo Large?
The interior laptop pocket comfortably fits 14" to 16" laptops, including MacBook Pro 16", Dell XPS 15, and ThinkPad X1 Carbon. The laptop sits flat against the back wall of the bag, protected by the leather on all sides.
Does it fit under the airplane seat?
Yes. The Hobo Large is designed as a personal item and fits under the seat on all major airlines. You can keep your laptop accessible for the flight without using overhead bin space.
Is there a zipper closure?
Yes. Unlike most totes that are open-top, the Hobo Large has a full-length top zipper. Your belongings stay secure in crowded airports, on public transit, and when the bag tips over under the seat.
What type of leather is used?
Full-grain leather — the highest grade available. It develops a natural patina over time and gets more beautiful with use. The leather is thick and structured, so the bag holds its shape whether full or empty.
What is Wool & Oak's Trustpilot rating?
4.6 out of 5 from 345 reviews (as of July 2026). For comparison, Tumi has 1.9 and Away has 1.7 on the same platform.
Named Best Garment Bag by Travel + Leisure · Best garment-duffel by Condé Nast Traveler
Founded in NYC · No outside investment · Designed by travelers








