The problem is you are looking for the collection in cart.items
instead of item.product.collections
.
Try this:
<td>
<a href="{{ item.product.url }}">
{{ item.product.title }} <br />
{% for collection in item.product.collections %}
{% if collection.handle == "collection-2014" %}
TOP: {{ item.variant.option1 }} - BOTTOM: {{ item.variant.option2 }}
{% elsif collection.handle == "collection-2013" %}
SIZE: {{ item.variant.option1 }}
{% endif %}
{% endfor %}
</a>
</td>