One of these makes a good-looking site with very little help. The other costs a fraction as much and gives you a file you can take anywhere. Most people choose on price and then discover which of those they actually valued.
Buying polish, or buying portability
Squarespace templates arrive looking finished and stay coherent as pages are added, with global type and colour settings holding it together as it grows. Squarespace scores 4 for design against WordPress.com's 3 and 4 for ease against its 3.
WordPress.com's argument is what happens afterwards. Content exports in a file another WordPress site will read, which means moving hosts is a migration rather than a rebuild — and WordPress is the software a very large number of sites already run on, so there is somewhere to migrate to. Plugins are available from the cheapest paid plan.
Squarespace exports too, so this is a difference of degree rather than kind. The WordPress export lands somewhere with a very large ecosystem waiting for it.
The renewal nobody reads
WordPress.com's advertised entry rate lasts twelve months and then renews at roughly two and a half times as much. That is the single most important number on this page and it is not the one on the pricing table.
Squarespace has no free tier, so the trial ends and a plan has to be bought — but the tier you buy is the tier you keep paying for.
Support is the other real gap. Squarespace scores 5 for support and WordPress.com scores 2, and help is available around the clock on every Squarespace plan. For somebody building their own site with nobody to ask, that is worth more than most feature comparisons admit.
WordPress.com also has more concepts to learn than a drag-and-drop builder — themes, plugins, settings that live in more than one place.
Which should you choose?
Choose Squarespace if you want it to look right without a designer and you would rather ask somebody than read a forum.
Choose WordPress.com if the content matters more than the container, you want it portable to real WordPress hosting later, and you have diarised month thirteen.

Squarespace
The builder to pick when the site has to look good with no designer involved.

WordPress.com
The managed version of the software a great many websites already run on.
Specs
Ratings
Ease for a beginner
Design and templates
Room to grow
Help when you are stuck
Value for money
Features
Pricing
Squarespace
WordPress.com
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