Try to upload the font under Content → Files
Copy the path and update in the css you have @font-face {font-family: ‘TrendSans Five’;
src: url(‘https://cdn.shopify.com/s/files -your-path’) format(‘woff’);
}
if you’re doing this inside .liquid file or Custom liquid sections, the code should be like this (if you upload to Files!):
(note how I am using both quotes and ticks to avoid nesting)
Also, if you’re uploading to Files, you can copy URL for these files and replace {{ ‘TrendSans Five.woff’ | file_url }} with the actual URL. In this case you can paste rules into Custom CSS (as liquid is not processed there).