It’s sad to admit it, gents, but summer is slowly coming to an end. In fact, in just a few short days, it’ll officially be fall. What’s that mean for you — other than less beach time, shorts and warm days? How about dusting off all of those fall outfits and preparing yourselves for the most stylish time of year.

The fall is, by far, the time when everyone is their most comfortable in their threads. From t-shirts and jeans to chukka boots and rolled khakis, there are endless possibilities when it comes to your fall outfits — assuming you know what the hell you’re doing.

Since we’re giddy about busting out some of the light sweaters and jackets, we’re here to help your style game in the next few months, telling you about some of the fall outfits men should always have in their rotation of clothing. Take notes and own some of these looks, because it’s the season to let your style shine bright.

Jean jacket

It’s not something that everyone can pull off, but, if you get the perfect fit, it’s simpler than you think. A jean jacket is a perfect complement to all your fall outfits, as it’s laid back enough for an afternoon stroll with some coffee, but works over a shirt and tie if you’re keeping things business casual on the way to the office. Make sure you get the right wash for you, though, and pair it with pieces of clothing that aren’t going to clash.

Chukka boots

For any guy whose ever owned a pair of Chukka boots — and there are plenty out there — you know why these things are a must-have for the fall season. First off, their always stylish. Second, they’re comfortable. Third, they’re versatile, capable of withstanding a little bit of rain while walking to a date, or just professional enough to look appropriate for an important meeting.

Fitted jeans

We emphasize the word “fitted” for a reason, guys. That’s because not all jeans are created equal. Sure, back in the day, the baggier the jeans, the better. But now that you’re an adult, it’s time to get rid of the bootcut options and focus on ones that sit on top of your sneakers or boots just right. More important than the cut at the bottom, though, is how a perfect pair of fitted jeans sit, resting right on the hips and showing off just enough of your toned leg muscles without looking too metro.

A favorite ballcap

Whether you’ve got a great head of hair or are fully bald, having a favorite ballcap to toss on is a must to accent your fall outfits. Keep things classic by wearing iconic brands like a New York Yankees hat, or get yourself a five-panel khaki hat that’s a little more stylish. Whatever your choice is, don’t always wear it, but leave it as an option for yourself on rainy or lazy days.

Go-to sneakers

Much like the aforementioned Chukka boots, a pair of go-to sneakers are always an essential part in completing your fall outfits. From a pair of Chucks to some old school Nike’s, these kicks should be clean and worn as a complement to the rest of your outfit. For instance, if you’re going with a chambray shirt and some maroon khakis, roll the bottom of the pants up a bit to show your ankle and let your new shoes get some looks. Perfect for a night out with the boys or a weekend of walking around, having a few pairs of go-to sneakers will serve you well this fall.


Flannel was made for fall, so don’t be the one guy who doesn’t include it into his wardrobe during the season. Plus, there are so many different ways to wear it that it’s almost a disservice not having at least one piece of clothing that’s flannel. Some guys like to wear a heavier flannel jacket for those cold nights, while others keep it stowed away in their closets till a weekend camping trip, and, finally, some dudes have a few flannel shirts in their fall outfit rotation that are a little more dressy. However you choose to wear it, remember that flannel is always in during the fall.

Don’t forget the shades

Just because the summer warmth is gone doesn’t mean it’s not going to be sunny during the fall, so make sure you always remember a pair of sunglasses before leaving the house. However, it’s important that your fall shades aren’t the same ones you’ve been wearing all summer long on the beach — so swap out those bright-colored frames for a pair of Wayfarers or Aviators. Fall sunglasses should be simple, classic and practical so they act as a complementary accessory to your fall outfit and not something that’s a distraction that ruins your look.