WHY I STOPPED: Stephen may be on vacation in Chicago from New York City where he works for Sony Music, but he doesn't let his style take a break. There are two parts of Stephen's look that I want to point out because they're perfect examples of some of this fall's hottest trends.
First up, Stephen's olive green bomber jacket. Truth be told, I'm seeing variations on this piece in almost every store this season. It's simple but effective; casual but approachable. While the jacket is clearly inspired by a military aesthetic, it crosses over into the type of outerwear that anyone would feel comfortable wearing. It's one of those staples for your fall wardrobe that you'll find yourself turning to over and over again. I picked up one of my own just a couple of weeks ago.
The second piece of Stephen's look I want to draw attention to is his navy-striped henley shirt. As you've probably guessed, I'm a huge fan of navy stripes. The white base keeps the layer neutral, but the horizontal stripes and vertical button placket add just the right amount of visual interest to make sure the shirt pulls its style weight. Paired with some eye-catching gold necklaces, gold-accented sunglasses, a pair of classic jeans, and some casual kicks, Stephen's look is completely current without drawing attention too much attention to itself.
STYLE TIP CHALLENGE: Bomb(er)s away! There are a thousand ways to pull of the bomber jacket. Check out the way Anthony from Oh Anthonio! pull it off here. Or Justin Livingston's brilliant combo here. Or Nick Pinsker's here. The options are endless. But if you're looking for a simple starting point, grab that olive green bomber jacket and pair it with a simple pair of fitted blue jeans and a simple undershirt (white, striped, or even flannel!). You'll be rocking simple, casual style with a minimal amount of effort.