17 Wardrobe Essentials That Will Never Go out of Style

Your 2020 Fall Wardrobe in 17 Pieces

17 Wardrobe Essentials That Will Never Go out of Style

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The weather getting cooler, the sun setting sooner, and the smell of pumpkin spice spanning far and wide can only mean one thing: Fall is here. It’s no surprise that this time of year is fashion’s favorite season. Sure, spring and summer are great, but as one season progresses into the next, we remove more clothing than we put on. Once autumn arrives, we start reaching for the layers, and after months away from the fleece, flannel, and full length pants, we are itching for a wooly change.  

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While Amazon and fast fashion brands have made adding to your wardrobe easier than ever, if you don’t have a good foundation to start, then you’re just buying clothes. A wardrobe is not only made up of trend-driven items that add excitement to getting dressed, but also core staple items that will always frame those items perfectly.

Below, we highlight those classic items that work this year, next year, and the next. Fill your closest with these and you’ll be stylish for the foreseeable future.   

Best Basic T-Shirt

Pact Stretch-Fit Crew Undershirt 4-Pack

Best Basic T-Shirt Pact Stretch-Fit Crew Undershirt 4-Pack

Let’s start with the basics — literally. You might as well start every season with a new 4-pack of these stellar undershirts because you’re going to be wearing the hell out of them all season long. Made from GOTS-certified, fair trade organic cotton with a hint of added stretch, these shirts are made to be worn as an under layer, but honestly, you want to show them off.  

$50 at WearPact.com

Best Dark Jeans

Levi’s 501 Jeans

Best Dark Jeans Levi’s 501 Jeans

You can’t go wrong with a crisp new pair of 100% cotton dark jeans from Levi’s. What’s great about this style is that they act as a clean slate. All those wear marks and worn-in whiskers will tell your story, not the story of factory fabricated fashion. 

$49.99 at Amazon.com

Best Everyday Sweatshirt

Entireworld Type A Sweatshirt

Best Basic Sweatshirt Entireworld Type A Sweatshirt

Something as simple as a sweatshirt can stand in for cozy clothes as much as it can stand up to even the dressiest casual event. Yes, every man should own a versatile sweater (we’ll get there) but today, with the way the world works, just because something starts with the word “sweat,” like this basic organic cotton and recycled polyester blend sweatshirt from Entireworld, doesn’t mean it’s built for the gym. In fact, quite the contrary. 

$88 at TheEntireworld.com

Best Bad Weather Boots

Hunter Original Play Insulated Rain Boot

Best Bad Weather Boots Hunter Original Play Insulated Rain Boot

If it’s fall, you’re going to need boots. The fact remains that the weather has become a phenomenon so unpredictable we no longer think twice if we get snow bombed on a Monday and end the week with an 85 degree day. So we should be prepared for anything. Hunter makes a boot for that. 

$105 at HunterBoots.com

Best Joggers

Lululemon License To Train Pants

Best Joggers Lululemon License To Train Pants

These days, we’re all pretty lucky — or unlucky depending on how you look at it — if we get out of our sweats more than once a week. Lululemon has led the way when it comes to clothing that looks like it could go to the office, but is built to kill it at the gym. These License To Train pants check all the boxes and they look great too.  

$118 at Huckberry.com

Best Flannel Shirt

Amazon Essentials Flannel Shirt

Best Flannel Shirt Amazon Essentials Flannel Shirt

Flannel is as ubiquitous to fall as flip-flops are to summer. If you don’t have a flannel shirt yet, make this year the year. One with a bold red base, like this one from Amazon Essentials, goes with just about anything you could want to wear heading into Q4, from jeans and a T-shirt (from above) to under a cozy fall sweater and a great denim jacket (down below).  

$18 at Amazon.com

Best Lightweight Sweater

Everlane Grade-A Cashmere Crewneck Sweater

Best Lightweight Sweater Everlane Grade-A Cashmere Crewneck Sweater

If we had to pick one color to wear for the rest of our lives, it would be navy. It’s cool, classic, and looks great as the color of everything from your best tuxedo jacket to your favorite pajama bottoms and anything in between. That’s where you find it now, as the color of the best cashmere sweater you can find — but with a twist. This crewneck from Everlane used a Donegal-inspired tweedy texture to make it stand out from other boring blues.

$130 at Everlane.com

Best Hoodie

Cuts Hoodie Classic

Best Hoodie Cuts Hoodie Classic

Known for some of the best fitting tees out there — it offers three hem styles to flatter just about any body — Cuts now offers the same comfy craftsmanship with it’s soft classic hoodie. A simple design in simple colors means this will last both in form and function.  

$118 at Cuts.com

Best Sporty Sneakers

Reebok Classic Leather Legacy Shoes

Best Sporty Sneakers Reebok Classic Leather Legacy Shoes

Boots are great — seriously, we love all types of the functional footwear — but sometimes all you really need is a good sneaker. Enter Reebok. The Boston-based brand keeps on releasing variations on its Classics and each one seems cooler than the last. It really took it a step further with this retro ‘70s-space-age inspired Legacy style. We approve, and we’ll be wearing these all fall and well into winter.

$80 at Reebok.com

Best Chambray Shirt

Proof Strong Shirt

Best Chambray Shirt Proof Strong Shirt

If you thought chambray was a summer shirt, think again. The breathable fabric feels like a denim on a diet, and is perfect for transitioning weather. Proof offers an exceptional example of such a fabric with it’s super durable Strong Shirt. Think of this guy as a chambray shirt on steroids. 

$128 at Huckberry.com

Best Trucker Jacket

Flint and Tinder Flannel-Lined Waxed Trucker Jacket

Best Denim Jacket Flint and Tinder Flannel-Lined Waxed Trucker Jacket

Flint and Tinder designed this waxed trucker last year and it has been an unchanged best-seller ever since. Warm enough for cool nights and cool enough for balmy days, this is a jacket that looks broken-in upon its first outing and only gets better from there. 

$240 at Huckberry.com

Best Puffer Vest

Nobis Chase Hooded Vest

Best Puffer Vest Nobis Chase Hooded Vest

The most lightweight down offering from Canadian brand Nobis, this vest is basically made for this time of year. With a Down Density Indicator (DDI) of one — meaning it’s perfect for mild climates — this stylish vest also manages to be machine washable, which makes keeping it clean year after year after year after year … 

$450 at Nobis.com

Best Socks

Bombas Brush Stripe Calf Socks

Best Socks Bombas Brush Stripe Calf Socks

Oh Bombas, how do we love thee? Let us count the ways. The superior comfort from the unique blend of 63% cotton, 30% polyester, 6% rubber, and 1% Spandex, the extra-long staple cotton, cushioned footbed, seamless toe, and one-of-a-kind honeycomb arch support system makes for a straight up, stay-up, superior sock. If that’s not feel-really-good enough, then remember, for each sock you buy, Bombas donates a specially designed pair to the homeless community. 

$12 at Bombas.com

Best Leather Boots

Ariat Wexford Waterproof Boot

Best Leather Boots Ariat Wexford Waterproof Boot

A boot to keep feet warm? Check. A boot to keep feet dry? Check. A boot to keep feet looking good? Oh yeah, check. Ariat offers the whole package with its Wexford waterproof boot. Known for standout western boots, these low profile Chelsea-style make a great grab-and-go boot when the weather is rough, and a great casual style when you want to look your best. 

$179.95 at Amazon.com

Best Lounge Pants

Italic Cashmere Jogger Pants

Best Lounge Pants Italic Cashmere Jogger Pants

Hell yeah we’re talking about cashmere comfy pants. Let’s get real, we’ve been stuck indoors for a while. Now that the weather is getting cooler, the socially distant beaches are closed and those long glorious outdoor runs will get shorter and shorter (or maybe in the gym … maybe) so loungewear is what we are living in for days at a time. Why not make what we wear as comfortable — read: luxurious — as possible? Luxury brands such as Brunello Cucinelli and Tom Ford have been pushing expensive lounge-like wear for a long time. And whereas it still might not be cheap, cashmere from the super secret at-cost DTC brand Italic for under $100 is a lot more affordable than most of the designer silky soft sleepwear you’ll find. 

$95 at Italic.com

Best Beanie

Lands’ End Rib Knit Beanie

Best Beanie Lands’ End Rib Knit Beanie

Lands’ End is bringing some serious style this fall (like, serious style) and to top it all off, we want to throw this hat into the ring. Fall is the perfect time to add a beanie your look to keep your head warm and your outfit fresh. 

$24.95 at LandsEnd.com

Best Trench Coat

Burberry Westminster Trench Coat

Best Trench Coat Burberry Westminster Trench Coat

If you take nothing else away from this list of fabulous fall items today, appreciate the appeal of the quintessential autumn sartorial addition — the Burberry trench coat. Thomas Burberry invented gabardine fabric in 1879, and the world has been more stylish for it ever since. This iconic label designs and creates its iconic item in England with signature features, including buttoned epaulettes, a buckled belt, and the classic Burberry check under the collar.

$2,190 at MrPorter.com

Sure, there are other clothes you could nab for fall, but these are the stylish staples that will get you from day to night all season long.  

You Might Also Dig:

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