If you are anything like me, the fall season consists of lots of outdoor weekend activities and travel to new and exciting places. Suddenly, apple picking, outdoor farmers markets, and nighttime fire pits on the lake all seem brand new again! The summer in New York City can be brutally hot, and outside of the beaches, sadly most people spend a lot of time indoors. As soon as the colder days of fall emerge, the welcomed crispness in the air seems to drive people right back into exploration mode! In fact, I just returned from an amazing road trip through Vermont, New Hampshire, and Connecticut (see a few of the posts here and here), and it got me thinking more about casual fall style. During this transitional time, I am always on the lookout for comfy but fashionable lighter weight outerwear options that can easily pair back to denim and slouchy knits. And of course, match the fall foliage! In the footwear category, I look for styles that are – of course – easily worn in the outdoors, but can transition back into city life. I’m loving hiker styles this season in particular and am finding them more versatile than ever before. This pair (also featured below), for example, look great in a casual context, but can also look so chic with tights, a paisley dress, and a leather moto jacket. But, back to casual fall style! See below to shop a few of my favorite looks.