Style sheets have existed in one form or another since the beginnings of Standard Generalized Markup Language (SGML) in the 1980s. Cascading Style Sheets were developed as a means for creating a consistent approach to providing style information for web documents.

As HTML grew, it came to encompass a wider variety of stylistic capabilities to meet the demands of web developers. This evolution gave the designer more control over site appearance, at the cost of more complex HTML. Variations in web browser implementations, such as ViolaWWW and WorldWideWeb, made consistent site appearance difficult, and users had less control over how web content was displayed. Robert Cailliau wanted to separate the structure from the presentation. The ideal way would be to give the user different options and transferring three different kinds of style sheets: one for printing, one for the presentation on the screen and one for the editor feature.

To improve web presentation capabilities, nine different style sheet languages were proposed to the World Wide Web Consortium's (W3C) www-style mailing list. Of the nine proposals, two were chosen as the foundation for what became CSS: Cascading HTML Style Sheets (CHSS) and Stream-based Style Sheet Proposal (SSP). CHSS, a language that has some resemblance to today's CSS, was proposed by Håkon Wium Lie in October 1994. Bert Bos was working on a browser called Argo, which used its own style sheet language called SSP. Lie and Yves Lafon joined Dave Raggett to expand the Arena browser for supporting CSS as a testbed application for the W3C. Lie and Bos worked together to develop the CSS standard (the 'H' was removed from the name because these style sheets could also be applied to other markup languages besides HTML).

Unlike existing style languages like DSSSL and FOSI, CSS allowed a document's style to be influenced by multiple style sheets. One style sheet could inherit or "cascade" from another, permitting a mixture of stylistic preferences controlled equally by the site designer and user.

Lie's proposal was presented at the "Mosaic and the Web" conference (later called WWW2) in Chicago, Illinois in 1994, and again with Bert Bos in 1995. Around this time the W3C was already being established, and took an interest in the development of CSS. It organized a workshop toward that end chaired by Steven Pemberton. This resulted in W3C adding work on CSS to the deliverables of the HTML editorial review board (ERB). Lie and Bos were the primary technical staff on this aspect of the project, with additional members, including Thomas Reardon of Microsoft, participating as well. In August 1996 Netscape Communication Corporation presented an alternative style sheet language called JavaScript Style Sheets (JSSS). The spec was never finished and is deprecated. By the end of 1996, CSS was ready to become official, and the CSS level 1 Recommendation was published in December.

Development of HTML, CSS, and the DOM had all been taking place in one group, the HTML Editorial Review Board (ERB). Early in 1997, the ERB was split into three working groups: HTML Working group, chaired by Dan Connolly of W3C; DOM Working group, chaired by Lauren Wood of SoftQuad; and CSS Working group, chaired by Chris Lilley of W3C.

The CSS Working Group began tackling issues that had not been addressed with CSS level 1, resulting in the creation of CSS level 2 on November 4, 1997. It was published as a W3C Recommendation on May 12, 1998. CSS level 3, which was started in 1998, is still under development as of 2009.

In 2005 the CSS Working Groups decided to enforce the requirements for standards more strictly. This meant that already published standards like CSS 2.1, CSS 3 Selectors and CSS 3 Text were pulled back from Candidate Recommendation to Working Draft level.

The CSS 1 specification was completed in 1996. Microsoft's Internet Explorer 3 was released in that year, featuring some limited support for CSS. But it was more than three years before any web browser achieved near-full implementation of the specification. Internet Explorer 5.0 for the Macintosh, shipped in March 2000, was the first browser to have full (better than 99 percent) CSS 1 support, surpassing Opera, which had been the leader since its introduction of CSS support 15 months earlier. Other browsers followed soon afterwards, and many of them additionally implemented parts of CSS 2. As of August 2010, no (finished) browser had fully implemented CSS 2, with implementation levels varying (see Comparison of layout engines (CSS)).

Even though early browsers such as Internet Explorer 3 and 4, and Netscape 4.x had support for CSS, it was typically incomplete and had many bugs that prevented their implementations from being usefully adopted.

When later 'version 5' browsers began to offer a fairly full implementation of CSS, they were still incorrect in certain areas and were fraught with inconsistencies, bugs and other quirks. The proliferation of such CSS-related inconsistencies and even the variation in feature support has made it difficult for designers to achieve a consistent appearance across browsers and platforms. Some authors resorted to workarounds such as CSS hacks and CSS filters.

Problems with browsers' patchy adoption of CSS, along with errata in the original specification, led the W3C to revise the CSS 2 standard into CSS 2.1, which moved nearer to a working snapshot of current CSS support in HTML browsers. Some CSS 2 properties that no browser successfully implemented were dropped, and in a few cases, defined behaviors were changed to bring the standard into line with the predominant existing implementations. CSS 2.1 became a Candidate Recommendation on February 25, 2004, but CSS 2.1 was pulled back to Working Draft status on June 13, 2005, and only returned to Candidate Recommendation status on July 19, 2007.

In the past, some web servers were configured to serve all documents with the filename extension .css as mime type application/x-pointplus rather than text/css. At the time, there was a software product on the market to convert PowerPoint files into Compact Slide Show files using the .css extension.