Kris Black - designer, author, cartoonist, & illustrator


My Journal provides an overview into the work and creativity of being a designer, author, cartoonist, and illustrator.


3 Easy Steps to Quickly Upload Images to Your Squarespace Website Using Skitch


I’m always looking for ways to speed up my workflow when building new, and maintaining existing, Squarespace websites. Adding images to a Squarespace site in a quick manner can help facilitate rapid testing of different ideas.

Fortunately, I’ve discovered a trick using a free app called Skitch that can help get images into Squarespace quickly.

What is Skitch?

Skitch is an idea and collaboration app that you can use to capture and share images. Skitch is available on your desktop for Mac and Windows computers, and it’s also available for iPhone, iPad, iPod touch, and Android smartphones.

Download Skitch, and review the wonderful step-by-step guides to help you get familiar with how to use Skitch.

You can sync Skitch on all your devices and computers by connecting Skitch to your Evernote account or creating a new Evernote account.

Evernote helps you to remember anything. You can store your stuff in notes, and those notes can be synced across all your devices with the Evernote app just like Skitch.

Three Easy Steps Using Skitch to Upload Images to Squarespace

For the purposes of this article we are using the desktop version of Skitch on either Mac or Windows. The process is the same on either platform.

Step 1: Decide Where You are Adding an Image in Your Squarespace Site

Before you capture an image with Skitch, decide where it needs to be added to your Squarespace site.

If you are adding an image to a page on your site, go ahead and add the Image Block or Gallery Block. See Chapter 12 - Adding Multimedia with Content Blocks of my book, Squarespace 6 For Dummies, about how to add either of these blocks to your site.

If you are adding an image to a collection item (album, blog, event, or product post), or a setting (page thumbnail, post thumbnail, or site logo), be sure to leave the image box open as seen in the following screenshot.

If you are adding an image to a Gallery Page, make sure you are viewing the Gallery Page within Content Manager.

Once an image upload area or box is ready to receive an image, you can proceed to Step 2.

Step 2: Capture an Image Using Skitch

Skitch provides several options to capture images, but the options available will vary depending on if you are using the Mac or Windows version of Skitch.

  • Fullscreen
  • Screen Snap
  • Timed Screen Snap (Mac only)
  • Camera (Mac only)
  • Open an Image or PDF (Mac only)
  • Picture Folder (Windows only)
  • Blank
  • Clipboard (Windows only)

Capture the image on your screen, and a Skitch window appears showing the image you captured. Use Skitch’s crop tool to get rid of excess image area, making your image as trim as possible. Then, proceed to the next step.

Step 3: Drag Your Skitch Image into the Image Block

At the bottom of the Skitch window is an icon of an image file. Click and hold on this icon, then drag the icon to your Squarespace site. Release it over the image area/box you prepared to receive your image in Step 1.

Your image will begin uploading to your Squarespace site. Once it’s done uploading, proceed as you would to save the image where it was added.


Adding images to your site using Skitch requires very little preparation. As I mentioned at the beginning of this article, I like to use this method to rapidly test image and design ideas on sites that I build.

If you have another technique for quickly uploading images to your Squarespace site, please share it in the comments.