I guess your template looks like this?
<title>Site administration | Django site admin</title>
<link rel="stylesheet" type="text/css" href="{{ STATIC_URL }}admin/css/base.css" />
<link rel="stylesheet" type="text/css" href="{{ STATIC_URL }}css/dashboard.css" />
Can you access both the files if you try opening them in your browser with the location that they should have? /media/static/admin/css/base.css
and /media/static/css/dashboard.css
(or maybe ../admin/...)
Have you added 'django.core.context_processors.static',
to your TEMPLATE_CONTEXT_PROCESSORS
?
UPDATE
It worked fine for me when I tried the same. In my template:
{% load staticfiles %}
<link rel="stylesheet" type="text/css" href="{% block stylesheet %}{% static "admin/css/base.css" %}{% endblock %}" />,
<link rel="stylesheet" type="text/css" href="{% static "admin/css/dashboard.css" %}" />
The rendered HTML (in my current project /static/
is my STATIC_URL):
<link rel="stylesheet" type="text/css" href="/static/admin/css/base.css" />,
<link rel="stylesheet" type="text/css" href="/static/admin/css/dashboard.css" />