Pricing (weighted 12%)
Free- WordPress is free and open source. Anyone can download the software and use or modify it to their heart’s content.
To get a site up an running you will have to pay for hosting. WordPress.org has a few suggestions for hosts that play nicely with the WordPress platform.
WordPress is obviously going to be less expensive. It is nice to get stuff for free, but there are a lot of reasons that Squarespace is worth the money.
$8/month - This is Squarespace’s least expensive package. They throw in a free domain with an annual purchase.
$18/month - This gives you more options if you are running an online store.
Squarespace does not have many pricing options, and they may are slightly more expensive, but they give you a fully featured website for eight dollars a month. WordPress will take some serious setting up. By contrast, Squarespace has a very concise and simple setup.
Design (weighted 12%)
There are many many WordPress themes all around the world wide web, so it is likely that you will find something to suit your needs. That said sifting through all of the theme can be a pain.
WordPress' editor is a bit old-fashioned. It does not have any drag and drop functionality, and it does not modify the themes in any meaningful way. Most of the design in WordPress is done through choosing a theme. The editor is mostly for changing around colors and text.
Squarespace's templates already feel like fully fledged websites. They are impeccably designed, but there are not that many. You might want to take care when making your site lest it resemble other websites made with Squarespace.
The editor requires a little getting used to. The design is very minimalist, so much so that it can be hard to navigate. Once you get the hang of it everything clicks into place, but it can be a little frustrating before that.
The sites themselves look great. They don't deviate too much from the templates, so they are going to look pretty great no matter what you throw at them.
Frontend Features (weighted 12%)
WordPress' frontend can vary widely. At its most basic it's a blog. At its most complex it's a fully featured website that just happens to be built in WordPress.
The mobile site depends entirely on your theme, but most will be optimized for mobile. The basic themes mobile sites look well, and they are easy to navigate.
Getting a fully featured website can cost you a lot of time and money. To reach the level of Squarespace's websites would probably require the skills of a website designer who specializes in WordPress.
Squarespace websites are all mobile optimized, so you will never have to worry about your site looking weird on a smartphone. They are acutely aware that people browse the web on their mobile devices just as much as on laptops or desktops.
Squarespace also gives you the normal options for website design. The sites look great and are really easy to navigate.
Backend Featuers (weighted 12%)
The WordPress backend is really easy to use. Everything is clearly labeled, so it is much easier to navigate than Squarespace's hyper-minimalism.
The backend will morph to fit your needs. At its most basic it provides a very stable blogging platform that will be more than enough for personal websites. At its most complex it can manage a fully featured website with dozens of pages and add ons.
The add ons are the stars of WordPress. Plug ins will greatly improve your website's usability, and they integrate seamlessly into WordPress' interface.
Squarespace’s backend suffers from the same excess of minimalism that plagues the editor. The backend is so minimal that it is sometimes hard to figure out where things are. That's remedied after spending some time with it, but new users will have to be patient.
The editor and the backend are very closely intertwined. That actually makes it very nice when you need to make edits. There is no separate window you have to open to switch between the two.
Hosting & Security (weighted 12%)
You’ll have to purchase your own hosting. WordPress only supplies you the software to make your website. They don’t put it on the web for you as well.
If you want SSL encryption in WordPress, you'll have to purchase your own certificate and set everything up. There are a few free plugins that make the process easier, but it is still more of a hassle than Squarespace.
WordPress comes behind Squarespace here. Squarespace is just better at getting your site online and keeping it online with minimal fuss.
Squarespace provides hosting with all of its plans. Their hosting is dependable and will handle any amount of traffic your website requires. They also very nicely throw in a free domain name.
Squarespace builds their own plugins and extensions. That makes their product more secure because they are able to curate how those plugins interact with Squarespace. It creates a closed ecosystem.
They also offer SSL encryption for the checkout pages in their eCommerce bundle. They don't offer sitewide encryption though, so all you encryption junkies are out of luck!
Reports & Statistics (weighted 12%)
WordPress requires that you use third party integrations to get statistics. The apps do integrate directly into the WordPress dashboard, and they are all pretty easy to use.
Just using free software it is possible to have a fully featured reports section in WordPress.
Squarespace has its own reports section. They give you a wealth of data. They give you basic traffic data, mobile views, subscribers, referrals, popular content, and search engine queries. That is a good amount of stuff.
Squarespace has a lot more statistics than WordPress offers natively, but WordPress has a lot more plugins that offer a more complete statistical picture.
Extensibility (weighted 12%)
There are tens of thousands of third party apps and plug-ins for WordPress. There are so many that it is a little silly to compare these two. WordPress has endless plugins that meaningfully change how your website works.
However, WordPress does not have the same closed ecosystem as Squarespace. That security boost is very nice.
Squarespace develops its own integrations. That makes it so that there are fewer integrations in Squarespace, but they are all made in house, preserving the security of the platform. What you lose in flexibility you can somewhat make up for in security.
They don’t have a PayPal integration, which is a bummer.
There are a bunch of not supported third party integrations for Squarespace, but use at your own risk. Squarespace won’t be able to help you if things go wrong.
Support (weighted 12%)
WordPress doesn't have any support beyond their forums. There is a lot of stuff floating around on the internet that will help you get started. So many people use WordPress that you will find the answers to most questions through a quick search.
Squarespace is a better bet if you foresee needing personalized support.
Squarespace has a number of support options. They provide how -to videos, forums, and a huge knowladgebase.
They also have live chat Mon-Fri 3am - 8pm EST, and are available through email. Both of these are tolerably quick to respond, but the live chat can be a little more sluggish.