Excellent with florals. Yes, keep the top 'pretty' and then the combat boots work.

Jessikams, I love the plaid shirt jacket, but totally get what you're saying. For sure, I usually wear it as comfort clothing--thrown over leggings and a tank for when I want to be cozy. For going out, combat boots go a long way to stop it looking like a nightdress, Same way they worked for Courtney Love's slipdresses back in the 90s.