Plaid dresses and skirt are my newest obsession. I love plaid, don’t get me wrong, but I’m usually much more of a plaid shirt or plaid blazer kind of girl. But this season, I’m loving all the plaid dresses and skirts that are everywhere. I think in the past I was worried they’d read too school girl, but in midi and maxi lengths, they feel more like a Ralph Lauren country catalogue than a prep school uniform. I fell in love with this Ganni dress the moment I saw it (it also comes in skirt form). Sadly, the dress overwhelmed me. It’s really cute and meant to be oversized but I just don’t think I’m tall enough (or maybe cool enough) to pull it off on its own. However, I loved it so much and it was cool out, so I threw a sweater over it for a weekend party in the country and loved how it looked, and I like that I can belt it and make it a little more functional sans a topper or layer it to it looks like a skirt. I ended up going with the cream sweater but I also liked how it looked with a fitted cardigan. I was in the country and it was muddy so I chose to pair with my favorite rain boots but it would also look cutie with heeled booties or riding boots. I love how this pattern works in the country, could be updated for the city with a leather jacket or more streamlined sweater or on its own with a belt, and would be perfect for a fall wedding in the country. I could also see taking this dress into the holidays with the right accessories. That’s the beauty of plaid — it’s so perfect for fall and the holidays/winter. Below I’ve rounded up some of my other favorite plaid skirts and dresses for the season at every price point.