The 2019 Style Guide for Men: Getting Ready for Fall

Posted on 15 August 2019
By Carlton Whitfield
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August is slowly creeping toward September, bright red sunburns have faded into a golden brown hue, and soon, the nights will start to get chillier as the seasons start to change.

For some, premature costume ads already have us thinking about how to throw the best possible Halloween bash. But before you set a date for your ghoulish affair and begin brainstorming costume ideas, you should take into account a more-pressing fashion matter: the need to transition your signature summer look into a refined fall aesthetic.

This is a particularly exciting time for men who care about their appearance. Sorry dudes, no one is impressed by your muscle tee/board short/flip flop combo. We don’t blame you for dressing sensibly and comfortably during the hot summer months, but frankly, the grab-and-go beachy vibe looks flat and lazy.

Now that you have the opportunity to wear a few more layers without becoming drenched in sweat, you can explore ways to dress casually smart this fall.

Here’s your go-to checklist to ensure you have all the basic necessities for upping your style game during this seasonal transition. Pro tip: take advantage of all the upcoming Labor Day sales to strike a bargain on your fall finds!

· A sensible under-layer

It’s time to toss those white, sweat-stained Hanes t-shirts that you wore beneath any SSBD (short sleeve button down) throughout the summer. In the fall, it’s all about the right layering strategy—especially as the months get colder. Pick up a few thermal Henley’s in earthy shades like olive green, burnt sienna, and brown, and make them your staple under-layer.

· A classic cardigan

Thick, knit cable sweaters and cardigans are the quintessential fall wardrobe piece. Creamy, neutral colours will be your best friend when it comes to matching all season long and dressing your ensemble either up or down per the given occasion.

· A reliable piece of outerwear

As the leaves change and temperatures drop, you’re going to want a trusty jacket to protect you from cold. The outerwear you choose says a lot about your style: all you the all-American, denim jacket type? Perhaps an edgy, leather moto bomber is more your speed? Or maybe you opt for an insulated windbreaker if you’re the athletic guy always on-the-go? There are tons of great options.

· A pair of dark denim jeans

Summer screams faded denim and hybrid men’s shorts, but fall is about clean, dark lines with fitted silhouettes. Added bonus if you pick up a pair of classic corduroys that exude the spirit of the season!

· A rugged pair of leather boots

Take a look at your footwear collection and upgrade as necessary when transitioning from summer to autumn. Dark brown leather boots lend a rugged aesthetic, perfect for all your favourite fall activities, but there’s also something about timeless white Converse that just never go out of style.

· A stylish pair of socks

No one wears socks during summer! It’s all about flip flops and soccer slides, whether you’re headed to the beach, chilling by the dock, or lounging by the pool. With fall approaching, we welcome the return of accessorising using stylish socks—so ditch those boring, white no-shows on whatever rack you found them on.

There are so many fun, stylish options for men’s crew socks that briefly come out to play whenever you cross your legs, go up a step, or adjust your pant leg. Rather than flashing an occasional ankle to unsuspecting viewers, show off your colourful pair of socks that add a dash of vibrant personality to your otherwise muted fall ensemble.

· A cap or beanie

When the elements come out to play, a piece of headwear can do you so many favours in terms of fashion and function. One, they put the finishing touch on your outfit by pulling it all together with a statement accessory. And two, they help prevent your body heat from escaping from the top of your head! Slouchy beanies, flat caps, and newsboy hats are our favourite styles.

· A sophisticated watch

Last but not least, a gentleman who wants to appear ultra-sophisticated when sipping bourbon by the fireside should pick out a statement watch that lends a polished and put-together look.

Enjoy dressing up this fall and don’t forget to grow out your beard for the ultimate fall appearance!