It's definitely time for some pre-fall boot shopping. Ankle boots are my favourite: I love tucking jeans into them. These Marcs (the billionth pair of Marc shoes featured on this blog) looks soft and cozy, even though it's a 3.5" killer heel. I love the bunched ankle cuff with the little belt. Plus they have a peep-toe and side cutouts to let in the summer breeze.
$590 CAD at ssense.com.