I'm trying to accomplish this (don't mind the red background)
So here is what I got I can get a border around the text but then I can't combine it with a text shadow... How can I get around this? Maybe it's something with :before :after statements?
h1, h2 { 
    font-family: Chicago;
    font-size: 38px;
    color: #FFFFFF;
    letter-spacing: 1.73px;
    
    
    
    /*
    text-shadow: 0 0 5px #000000; 
    
    THIS WILL GIVE THE TEXT THE SHADOW*/
    
    text-shadow: -1px 0 black, 0 1px black, 1px 0 black, 0 -1px black;
    /*THIS WILL GIVE THE TEXT THE BORDER*/
    
    /*How can I combine these two?*/
}
<h1>CSS ZEN GARDEN</h1>
<h1>THE BEAUTY OF CSS DESIGN</h1>
CSS Syntax Note: To add more than one shadow to the text, add a comma-separated list of shadows.
By using a comma, we can specify multiple text shadows. Here we have created the first text shadow with the same color as th background to give a semi-3D effect.
Answer: Use the CSS text-shadow property You can simply use the CSS text-shadow property to apply the shadow effect (like Photoshop drop-shadow style) on text elements. You can also apply more than one shadow (applied front-to-back) through providing a comma-separated list of shadows.
Sometimes we need to create text and adding the outline to the text. There are mainly two methods to create a border to the fonts which are listed below: Using text-shadow property. Using text-stroke property.
Maybe this solution is what you are looking for:
h1 {
   -webkit-text-stroke: 1px black;
   color: white;
   text-shadow:
     3px 3px 5px #000,
     -1px -1px 5px #000,  
     1px -1px 5px #000,
     -1px 1px 5px #000,
      1px 1px 5px #000;
}
<h1>CSS ZEN GARDEN</h1>
<h1>THE BEAUTY OF CSS DESIGN</h1>
have a look at this fiddle. you have to use -webkit-text-stroke and then you can use the stroke and shadow separately
h1, h2 { 
    font-family: Chicago;
    font-size: 38px;
    color: #FFFFFF;
    letter-spacing: 1.73px;
    -webkit-text-stroke: 1px black;
    }
<h1>CSS ZEN GARDEN</h1>
<h1>THE BEAUTY OF CSS DESIGN</h1>
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