I recently read declarative design by Jeremy Keith. In the post he discusses different approaches to writing CSS in terms of declarative or imperative design where declarative is used to describe CSS authoring techniques that leverage the power of CSS and the cascade such as Utopia Every Layout and intrinsic design and imperative for tools such as Tailwind.
I found his framing is a refreshing break from the usual mud-slinging arguments around this topic "CSS is terrible!", "Tailwind!? Might as well use inline styles!":
I’m not saying that declarative tools—like Utopia—are right and that imperative tools—like Tailwind—are wrong. As always, it depends. In this case, it depends on the mindset you have...
...I wonder whether your path into web design and development might also factor into which end of the spectrum you’d identify with. Like, if your background is in declarative languages like HTML and CSS, maybe intrisic web design really resonates. But if your background is in imperative languages like JavaScript, perhaps Tailwind makes more sense to you.
My background in web development is definitely HTML and CSS, and my preference is definitely towards the "CSS is awesome" end of the spectrum. I love the power and flexibility that comes from using intrinsic design techniques such as those in Every Layout. The ability to build responsive sites that don't need media queries, and just adapt to the viewport size is incredible.
Having said that I've also used Tailwind, going so far as to choose it as the default option at my previous agency. In that context I found the consistency, and simplicity1 of Tailwind was a great benefit – the fact that the same styles and classes would be available across all of our projects made context switching or going back to prior projects so much easier. However I definitely missed some of the flexibilty of the intrinsic approach, so much so I made Tailwind Utopia a tailwind plugin for using a Utopia fluid type scale.
I definitely agree with Jeremy that the underlying philosophy you bring to these tools will influence your experience of using them. While I believe Tailwind was the right choice in the agency, and being able to throw classes in the HTML was fast (even enjoyable), it always felt a little bit like going against the grain.
1 Many would disagree with calling Tailwind simple! I foundthat techniques such as those in Every Layout while powerful, require an in-depth knowledge of the intricacies of CSS that made it harder for the whole team to understand and edit the styles with confidence. In comparison, Tailwind was easier to understand, and had excellent up-to-date documentation.