15 Ridiculously Cool and Easy Outfits to Wear This Fall

Image via Complex Original

Brogues and their chunky profile mix better with the thicker garments that are worn after Labor Day. Toss a commando sole on them, and they're virtually a pair of boots. This mean you can wear them with darker shades that tend to dominate fall style such as olive, grey, and black.

Tricker's Ilkley Brogue, $525

If you don't want to go all-out camo this fall, you can sport it in the details such as the lining of a jacket's hood. It will be enough color to carry a whole 'fit. All you need to complete the outfit is an oxford shirt and pair of denim.

nanamica Gore-Tex Cruiser Jacket, $1150

If you're not ready to go full-on cozy boy this fall, you can always opt-out the sweats for a pair of jogger pants. They can be worn with a T-shirt, but with a button-up or virtually anything else, too. Pair your joggers with a shirt buttoned to the top. You can easily throw on a blazer or sweatshirt to complete the look.

Publish Bedrich Jogger, $85

The fall is a time to dress a little more rugged. Not only is it slightly colder outside, but it's also great to go exploring in the woods as the leaves change. For this, you'll want a pair of pants that can take a beating but are more comfortable than jeans. Find something in rip-stop cotton that you can pair with a utility shirt and hiking boots, but keep things casual and street with a trusty snapback.

Topo Designs Mountain Pants, $129

Layering is the best thing about fall style, and fleece jackets are a choice piece this season. Instead of making fleece your final layer, which is OK, too, try it underneath a light windbreaker. You can easily put this look together with a pair of slim chinos and grey New Balances or lightweight running sneakers.

Norse Projects Frederik Thermal, $312

The camo trend continues to march on. Instead of going streetwear or heritage with this military look, try and wear it with an all-black ensemble this fall. It serves as the perfect canvas for the print to pop, and can be complemented by a pair of brown or tan sneakers.

A.P.C. '70s Army Jacket, $415

Tie-dye was huge this summer, and while we don't recommend wearing your light, breezy T-shirts into the fall, there are still ways to get trippy. Placing a subtle, tie-dye button-up shirt underneath a monochromatic outfit lets the print stand out, but doesn't scream August music festivals.

Our Legacy Classic Shirt Indigo Tie-Dye, $225

What would fall be without sweaters? Instead of wearing a crewneck that you'll be stuck with all day, try out an oversized cardigan that can easily be layered or removed. With this 'fit, keep it classic with an oxford shirt, chinos, brown belt, wingtips, and added warmth from a watch cap.

Club Monaco Fleece Shawl Cardigan, $130

Trucker jackets are a staple for any season, but its great to have one in your arsenal that's not denim. If corduroy pants aren't your thing, there's also corduroy jackets. They have a texture that will add difference in your layers, and go well with dark, rigid denim. Which you should start breaking in pronto.

Supreme Corduroy Snap Front Jacket, $178

When it gets a little colder outside, a natural reaction is to reach for your favorite sweatshirt. For most of us, this means we're wearing streetwear. This season, don't go for anything too bright, but you should sport the most recognizable logos from iconic brands. Wear it by itself, or as the base for any of your jackets.

Stussy SS Link Sweatshirt, $68

You're going to watch football at some point between now and February. If you don't have any jerseys in your wardrobe, there's always the go-to option of the varsity jacket. But if you never played sports, that's when you'll stunt in something next-level. You'll want something unbranded and without patches. It can be worn with a plain T-shirt and black jeans and become your weekend uniform.

Wings + Horns Varsity Jacket, $845

Wearing multiple pieces of denim can be tough without looking like Jay Leno. But if you wear alternating shades of indigo, then it can be easily pulled off. We think it looks best when the jacket is darker than the shirt.

Levi's Commuter Trucker Jacket, $128

Bucket hats aren't going away just because it's no longer August. You just need to switch up how you wear them, and let their 360-brimmed functionality shine in new ways. Instead of shielding your eyes from the sun, they can protect your dome from the rain and cold. To further prove this point, wear a minimalist parka and pull off an Inspector Gadget steez that doesn't suck.

Soulland Penny Navy Bully Hat, $103

On a cold, damp fall day, we all just want to lay on the couch and wear warm clothes. If we need to go outside, we want the same comfort as our lounging gear. Luckily, there's such a thing as slim-fit fleece pants, and they go perfectly with a sweater, water-repellent outerwear, and topped off by a 5-panel cap. It's not science, it's just a cheat code to looking fresh.

Creep Polar Fleece Hike Pants, $260

Shawl collar sweaters can be hit-or-miss. But when they come dyed in indigo, they're a definite win. If you want the denim look, but not the discomfort, place this cozy layer above a flannel with a pair of chinos. The colors are hard to mess up, and can be inter-changed with other pieces in your wardrobe.

United Indigo French Terry Shawl, $198