Outside Insiders

Outside Insiders (OiiO) - A collection of four canvas messenger bags in tan, green, brown, and black colors, with a close-up of a tan bag showing various pockets, zippers, and a shoulder strap against a plain background.

“For the movers, the makers, the curious.”

Bags that keeps up with wherever life takes you — from morning commutes to hidden trails and spontaneous detours.

SHOP NEW ARRIVALS

Essentials for every kind of day — designed to keep you ready, wherever life takes you.

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The Axis I Convertible Canvas Sling Backpack
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The Axis I Convertible Canvas Sling Backpack
$64.99

One bag. Two ways to carry it.

Wear it across your body for quick access. When you want the support of a backpack, unzip the strap and switch the carry.

• Converts from a crossbody sling to a backpack
• Made from 100% cotton canvas
• Built-in organization for everyday essentials
• Adjustable for a comfortable, hands-free carry

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The Ashford Canvas Backpack
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The Ashford Canvas Backpack
$144.99

Workweek to weekend.

The Ashford keeps your laptop and tablet protected during the week, then gives you room to pack up and go. With a dedicated device pouch and a spacious main compartment, it is made for commutes, overnights, and weekends away.

  • Fits laptops up to 16 inches

  • Fits tablets and iPads up to 13 inches

  • Dedicated device pouch

  • Room for work gear and a weekend away

  • 100% cotton canvas

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The Pathfinder Key-Closure Leather Journal
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The Pathfinder Key-Closure Leather Journal
$28.00

Handcrafted Key Papel Leather Journal

For ideas worth keeping.

Handcrafted by Key Papel from the Outside Insiders Shop × IndigoBlueMermaid collection. Handmade paper pages, a genuine leather cover, and a wrapped key closure make this a journal to write in, sketch in, and keep.

  • Handmade paper pages

  • Genuine leather cover

  • Wrapped leather key closure

  • Choose smooth leather or an etched design

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The Pivot Canvas Backpack
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The Pivot Canvas Backpack
$99.99

Your whole setup, within reach.

Laptop, tablet, charger, small essentials—the Pivot gives each part of your day a place. A dedicated device pouch fits up to a 16-inch laptop and a 13-inch iPad, while exterior pockets keep the things you reach for from disappearing inside.

  • Fits laptops up to 16 inches

  • Fits tablets and iPads up to 13 inches

  • Dedicated device pouch

  • Exterior pockets for grab-and-go essentials

  • 100% cotton canvas

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About Us

OI creates essentials for people who live in motion. Founded by a veteran with a passion for practical design, every piece blends style, function, and purpose — so you can focus on what matters most.

Designed for the Way You Move

Learn more about OiiO

Trusted by Outside Insiders everywhere

  • "I’ve been using this sling bag every day, and it’s perfect. It fits all my essentials without feeling bulky, and it still looks stylish for work or running errands."

    Aisha J.

  • "This bag has been a game-changer for weekends. I can carry my water bottle, notebook, and camera comfortably, and it’s light enough to take anywhere without getting in the way."

    Jordan L.

  • "Shopping is so much easier with this crossbody. I can keep my hands free, carry everything I need, and it’s durable enough to last. Definitely my go-to bag now."

    Riley M.