September is, without a doubt, one of the trickiest fashion months of the year (Get it? Because it's Fashion Month). Whether you're spending it running from show to show, looking for the perfect back to school outfit or just trying to survive the seasonal transition period, there's nothing easy about dressing for the first month of Autumn. With that being said, it's about time we suck it up and get thinking about what the hell we're going to wear this month.
It's a bit too early for our usual fall go-tos (read: chunky knits, ripped jeans, sweater dresses and more), but there are a few transitional fashion items that we can move into the rotation. Cowboy boots (or cowboy mules) can slide into the place where your strappy sandals used to be. Hats, tights and scarves can be slowly reintroduced into your wardrobe — even if they're still of the summer variety. And we can finally start swapping out our everyday tank tops for t-shirts and lightweight sweaters. Trust us, it won't be easy to make the leap from summer to fall, but with a little help from the masters, it can be done. We promise.
So to ease the awkward pass-off from August to September, we rounded up some outfit inspo ahead. If you follow the leads of these street style stars, maybe, just maybe, September won't be the hot mess we were expecting it to be.