August isn’t the most straightforward month. It’s got both the pressure to wear those stereotypically summery things while you still can and the itch to get all back-to-school with the new fall stuff creeping into stores. It’s confusing—but also liberating, if you play it right. On hot days you can still dress in white jeans and strappy sandals like it’s a Memorial Day barbecue, but on cooler evenings you won’t look out of place in a little cardigan and maybe even something plaid. Odds are your best friend couldn’t wait to break out her new fall swag either.
You have so many options (too many?), so for a template of where to start getting dressed in the morning (or at night), we’ve rounded up some particularly great outfits from our favorite celebrities, street style stars and our very own Community members. Whether fail-safe or creative, each one’s an inspiring look. Click through to see all 31 of them, one for every day of the month.