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Summer might be over, but now the fun of fall dressing begins. New season, same you, but with next-level style to conquer transitional weather like a champ. It’s the perfect time to step up your wardrobe game with cool new outfits for any and all occasions. From budget-friendly fashion that won’t break the bank (after that pricey summer vacation) to lust-worthy designer duds that hit the latest fall menswear trends, here are five outfit ideas for men for stepping out in major style this season.
Let's start with the not-so-basic basics! If there's one investment piece you can rock year after year, it's a stellar leather jacket. While the inexpensive option sounds appealing, you'll still want to look for a high-quality leather that's durable and will wear-in like vintage. The Arrivals Ford leather bomber isn't cheap, but the luxe touch of a buttery leather jacket in a classic shape rarely comes at a price this low.
Dark denim was made for the fall season, but this season more than ever, multiple designers had dark indigo denim going down the runway. Everlane is here to help you rock the classic-yet-trendy denim duds for a price that's totally reasonable. Plus, it has that hint of stretch you need to move comfortably through all your fall adventures.
While you might expect a classic cap and white button-down oxford in a flattering slim-fit to make it on your fall shopping list, a stylish Chelsea boot is just as essential. Most men might associate this style of footwear with trendy rock stars, but it's versatile and flattering for the Average Joe to sport from work to a night on the town.
Shop This Look:
The Arrivals Ford Leather Bomber, $495, the arrivals.com; Mr P. Button-Down Oxford Shirt for Men, $160, mrporter.com; Everlane Men's Slim-Fit Jeans, $68, everlane.com; Florsheim Belfast Chelsea Boot, $130, nordstrom.com; Reigning Champ Baseball Hat, $60, eastdane.com
Returning to the regular work week and saying goodbye to summer Fridays isn't easy (we feel your pain!), but it's the perfect time to upgrade your workwear wardrobe with a snazzy look that shows you're ready for a promotion. With the transitional weather, layering is key to getting through the day comfortably. Business casual dressing might be confusing to some guys, but it's easy to create an everyday uniform that feels as good as it looks.
The turtleneck made a comeback last fall and shows no signs of going anywhere for a dapper-yet-comfy knit. Mustard yellow is easier to pull off when layered under a striped button-down shirt for just a pop of color. Just make sure to keep your trousers classic and pattern-free to not overwhelm everyone during an important meeting.
Simple Chelsea boots can pair perfectly with a large designer leather tote to hold all your gear with killer style. Spending some extra bucks on a large leather accessory is worth every penny when you can pair it with inexpensive clothes for an elevated high-low outfit.
Shop This Look:
H&M Men's Regular-Fit Button-Down Shirt, $24.99, hm.com; Acne Studios Men's Norton Slim-Fit Sweater, $290, mrporter.com; Saturdays NYC John Chino, $175, endclothing.com; Florsheim Belfast Chelsea Boots for Men, $130, nordstrom.com; MCM Traveler Striped Traveler Tote, $725, mcmworldwide.com
Sport a casual, cool look for all your fall tailgating fun. Game day is more about the comfort food and a cold one, but you can still look effortlessly stylish while cheering on your team of choice.
Bombers are big in menswear, and brands like Eddie Bauer are #winning for their dapper and functional fashions. This 650 fill Premium Down bomber will have you feeling warm even after hours in the great outdoors on a chilly fall day (and without adding major bulk to your bod).
We love a team jersey, but if you're not representing a specific team during the big game, Tailgate is perfect for repping your alma mater with tees that have a lived-in vintage look. Any slim-fit jeans will really do, but if you're in the market for new denim duds, you can't go wrong with a rugged-yet-stylish distressed jean with stylish paint splatter accents. Top it all off with your trusty wool baseball cap, and your game day look is gold.
Shop This Look:
Eddie Bauer Men's 1936 Skyliner Model Down Jacket, $139.99, eddiebauer.com; Tailgate Men's NYU Ringer T-Shirt, $32, ae.com; Frame Men's L'Homme Slim Jean, $130, frame-store.com; DKNY Samson Graffit Leather Sneaker, $125, dkny.com; Reigning Champ Baseball Hat, $60, eastdane.com
When it's Saturday night and the feeling is right, it's time to keep it classic with a stylish twist. Beyond your dapper leather jacket, rock a classic button-down, or go for one with a Mandarin collar for an unexpected touch to your slim-fit shirt. Upgrade from a typical pair of trousers to an option that has a side-stripe detail or jacquard print for a little extra oomph to your outfit. Keeping the silhouette slim will have you looking lean and sharp with little effort.
Rock Chelsea boots, or score a second pair with a little hint of badass, like Aldo’s Afille boots that have straps and hardware detailing. It’s a bit of edge, without looking like you’re joining a biker gang.
Lastly, no evening look is complete without a touch of jewelry. Miansai is a brand to know for their simple metals and cord bracelets that give any outfit a stylish accent. The guys’-night-out vibe is all about effortless style with a touch of ‘tude.
Shop This Look:
The Arrivals Ford Leather Bomber, $495, the arrivals.com; Mr P. Grandad-Collar Button-Down Oxford Shirt, $165, mrporter.com; Topman Black Skinny-Fit Side Taping Pants, $110, topman.com; Aldo Afille Boots, $150, aldo.com; Miansai Gold Nyx Cuff for Men, $285, miansai.com
How can you feel relaxed but also look cool enough for a day of errands in your sweats? It’s all about adding cool pieces in your wardrobe to your go-to sweats outfit. Designers like Versace were mad for plaid this season, but you can avoid the designer price point by entering the “plaidiverse” of JC-RT. This designer duo knows a good plaid shirt like no one else, and after one purchase, you’ll be hooked on the stylish lumberjack look.
Layer a T-shirt that’s cool and limited-edition, too, for added edge. Hiro Clark partnered with the Classic Car Club to make a dope T-shirt for guys who have a need for speed (but not necessarily the funds for a vintage Porsche). A cool pair of shades is essential for any morning hangover, and these Clubmaster sunglasses are a sure bet at a reasonable price.
Your sneakers might normally seem like an after thought, but after scoring the new collaboration between JW Anderson and Converse, you’ll want to plan your whole outfit around these chic kicks. It’s the laid-back comfy look you love, but it's fashionable enough that you’ll still get compliments.
Shop This Look:
JC-RT Plaid Shirt, $125, jc-rt.com; Hiro Clark x Classic Car Club Sweet Ride T-Shirt, $128, hiroclark.com; Champion Men's Reverse Weave Sweat Pant, $79, endclothing.com; Ray-Ban Clubmaster Sunglasses, $153, nordstrom.com; Converse x JW Anderson Patent Leather High-Top Sneakers, $150, lyst.com
Concerts don’t end with Summer! Store your cool graphic T-shirt and score a killer hoodie to rock to the live show with distressed light blue jeans. It’s casual-cool with a streetwear vibe that’s perfect for hours of taking in your favorite artists, while staying comfortable AF. To add some major interest (and warmth) to your look, this Alpha Industries bomber jacket brings out the pop of orange on your hoodie, keeping you protected from that cold-weather chill.
The most important part for any concert is the right combination of accessories for your cool factor. Layered necklaces from H&M add some interest and personality to your streetwear-inspired look for an affordable price. There’s no better time to show off your latest adidas sneakers for long hours of rocking out, and show the crowd you’re sporting the must-have kicks of the moment.
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Alpha Industries Reversible Water-Resistant Jacket, $150.00, nordstrom.com; Nike Logo Hoodie, $59.00, endclothing.com; Rag & Bone Slim-Fit Distressed Jeans, $275.00, mrporter.com; H&M 2-Pack Necklaces, $9.99, hm.com; adidas Yung-96 shoes, $100, adidas.com
It’s the perfect time to explore the great outdoors! Go on an adventure to any countryside, while wearing a rugged-yet-stylish look that can go from a long hike up a mountain to a cozy dinner by a fireplace. Break out the puffer vest you wear for a cool fall-layering look and it’ll keep you seriously warm, without making you break a sweat. It's a perfect moment for sporting your favorite new flannel for a nod to Paul Bunyan, but keeping it fashionable in one of the trendiest colors of the moment in menswear.
Everlane’s perfect slim-fit dark indigo jeans will get a lot of use this season, and look stellar with your town or country look. To keep you warm while you’re out in the brisk fall weather for the day, make sure to break out a cool beanie for a winter-hat look that adds an effortlessly cool vibe to your outfit. Florsheim’s Foundry collection chukka boots complete the look, made of high-quality leather from Horween (an American leather factory since 1905) that’s oh, so soft and durable for any trail, yet looks great to wear out to dinner.
Shop This Look:
Eddie Bauer Down Vest, $56.00, eddiebauer.com; Ovadia & Sons Plaid Flannel Shirt, $260.00, nordstrom.com; Everlane Men's Slim-Fit Jeans, $68, everlane.com; Florscheim Foundry Plain Toe Chukka Boot, $280.00, florsheim.com; Iron and Resin Watchman Beanie, $28.00, bespokepost.com