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I am about to design an IOS 8 app for the very first time.

I've been a designer for 5 years now, both on Photoshop and Illustrator, but I never got the change to design an app. I am looking for some guidelines.

My questions are: Which program should I use? Photoshop or Illustrator? I am much more comfortable on Photoshop, but I am afraid of the sizing. Which brings me to my next question, which canvas size to pick, iPhone 4, 5, 6 or 6+? Or maybe a design for each size (same style though)?

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First and foremost you should start at "Designing Great Apps" and "Designing for iOS". If you don't aware of these sources your app certainly will be rejected by Apple.

What to use? Anything you are most familiar with, Illustrator, Photoshop, Pixelmator or any other app you can run, and better - on Retina display.

You should perform a lot of searching and planning ahead of placing any single line on your graphic software - you deal with Apple and should clearly understand what they want from you and what you want from the users.

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Adding to Ilan's answer, here's another resoure you will find useful:

> The iOS Design Cheat Sheet

The site states the different sizes and resolutions for iPhone and iPad, as well as instructions on typography, icons, corners, grids, bars and tables.

Regarding workflow, take a look at Marc Edwards' App Design Workflow. He starts with a 1x (non-retina) mock, to work with elements at their true -snapped to 1px grid- size, and uses Photoshop to create and export the assets.

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Since some time has passed, I just wanted to get some things out here:

There are programs such as Adobe Experience Design and Sketch (Mac only) which are really great for designing UI. Other than that Photoshop as well as Illustrator are perfectly capable of vector-designs (though Illustrator might be better suited) for exporting at various screen sizes without losing quality.

As for the canvas size, it is best to design at what they call "1x", which would be the smallest possible screensize that can than be upscaled accordingly. For iOS this would be 375 x 667 pixels (iPhone 6 and 7, SE uses some different aspect ratio).

As for guidelines, this site here might also be quite helpful as well.

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