The BroBible Style Guide: How To Dress Rugged And Warm This Winter


When it comes to shopping for the holidays (…or yourself, let’s be real), you want worthy gifts or wardrobe staples that will stand the test of time and not end up in a landfill come next winter while you ask yourself how hungover you were when you bought it.

As far as your personal style goes, you need a rugged aesthetic that can withstand the elements — or at the very least, your morning commute. However, rocking outdoor-ready style can be a fine line to walk if you don’t go about it correctly. You don’t want to look like a full-blown lumberjack that’s ready to WIN Oregon Trail, no matter the dysentery risks. Leave that for the Brooklyn Dads. You need to balance the consummate, tailored professional you are with the weekend warrior inside, ready to rage with a cast iron skillet and bottle of decent whiskey at a Hudson Valley Airbnb.

Without further ado, here’s a no B.S. cold-weather style guide for you and your loved ones that you can cop for yourself or holiday gifts.

Lugz Mallard Boots

Boots that look good, feel good and are slip resistant make up the foundation of a solid cold weather wardrobe. These are the duck-toe boots you can bring on a backpacking trip or wear while waiting in line at Starbucks on a slushy day, because late stage capitalism gets us all. At six inches tall these Lugz are just the right height to keep out the snow and rain, but can just as easily be worn with your favorite flannel at a sunny tailgate.

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J. Crew lightweight denim shirt in dark wash

Denim shirts are a great staple regardless of the season, so you can wear this gem year-round. Darker denim also has the advantage of being more elevated than lighter chambray so you can throw this under blazers, cardigans if you’re feeling very Autumn Area Man™ or on its own with the bottoms of your choosing. It’s also available in slim or tall options, so you can grab the fit that matches your frame.

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Woolrich Buffalo Check Flannel

When it comes to flannel, this buffalo check style earns extra points for taking no prisoners and going for the full winter aesthetic. If this shirt were a person, he would have already hunted down dinner with his bare hands, built a roaring fire with whiskey used as fuel, and seamlessly offered the meal on a bark-rimmed hewn platter to your (former) girlfriend.

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Cedarwood Beard Oil

Beard grooming isn’t a hipster-instigated fad or something to be ashamed of, but a point of pride and a necessity for looking properly put together. Also: Beards can scratch your partners face, and no one likes waking up feeling like they have rug burn because you haven’t tamed your unruly mass of man scruff. That’s when you get kicked out without coffee. This bottle keeps your hair soft with a fresh, clean scent that won’t clash with your cologne.

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Gant Cotton Cashmere Check Shirt

A muted plaid that pops in the right way will get you noticed without making you look like an asshat. This one is polished enough for the office and can make itself comfortable at your usual watering hole. The cotton cashmere blend makes it soft and breathable; two things you’ll need when it’s freezing outside but your building super didn’t get the memo that your apartment shouldn’t feel like an inferno.

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The original Westerley – Pendleton

Just like a rug that really ties the room together, this sweater will do the heavy lifting when it comes to making a statement. Relax and enjoy a white Russian in this coveted 1972 original that also doubles as a Halloween costume. You may not be in a Coen brothers movie, but you can still use this wool zip-up as a conversation starter or to cement yourself as the damn champion of your bowling league.

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White and Green Pattern Old Navy Flannel Scarf

Scarves are a necessity in freezing weather, no matter how badly you want to fight the elements. While cashmere or wool blends are preferred, at its price point this Old Navy option can be tossed around and shoved in the back of your truck without a second thought. However, its traditional green and white patterned plaid won’t disappoint you or embarrass your sig other — two very important emotions to consider while making sartorial purchases.

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Yes Barbour jackets are expensive, but they’re indispensable, timeless, and make you look like you just stepped out of the British countryside — kryptonite for many, many members of the opposite sex. Plus they’re a one-time investment you can pass down to your spawn. Remember to not toss it in the wash and get it re-waxed every few seasons so the cotton can still repel water.

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Gap Flannel-lined Khakis

Khakis can easily become the workhorse of your wardrobe and make you look like the productive member of society that no one at dollar-beer-night-that-turned-into-the-early-morning expected to see. This flannel-lined style can be cuffed to show off the pattern, or keep ‘em on the straight and narrow and just enjoy the extra insulation against Mother Nature’s Stage Five clinger embrace.

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Carhartt Beanies

Winter hats are highly underrated. They literally cover all manners of sins like bad hair days, or just look good while keeping your head warm. This Carhartt gem is an understated essential that’s anything but fussy, and can still make an appearance around town. Like an urban woodsman who demanded an espresso machine in the cabin he built with his two properly moisturized hands.

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Stanley flask

Hands down, one of the best flasks out there. It’s utilitarian, streamlined and doesn’t look bad on your bar cart or shelf. What’s more, it can take a beating so when you’re running out the door and remember you nearly forgot your train buddy, you can toss it in your bag and keep going. They also make excellent stocking stuffers.

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Lugz Empire Hi WR

Water-resistant and made to move thanks to memory foam technology, these Lugz slip-resistant boots can kick the hell out of your to-do list. When you’re done lugging timber (or at least posing like you did), these boots can walk you over to the nearest bar with a decent shot and a beer special. The embodiment of form and function, you won’t think twice about pulling on these boots.

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Timex Weekender

An affordable but handsome field watch says a lot of things about the wearer. Sported on the weekend it nonchalantly says, “I leave the more expensive option for the board room”, or “screw your ten thousand dollar accessory, this looks good.” The great thing about Timex’s is that you can swap out the strap depending on your mood, season or occasion. But this green option is a timeless (sorry) neutral that should do the trick.

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Filson bag

The tagline doesn’t lie – Filson bags were made to last and don’t look half-bad too. This duffle meets the maximum carry-on restrictions and is made of rain-resistant twill and a rust-proof brass zipper so it won’t self-destruct on you a couple thousand of miles away from home. Yes this isn’t a cheap bag, but isn’t carrying something you’re not embarrassed of while traveling and upping your airport Instagram game priceless?

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The BroBible team writes about gear that we think you want. Occasionally, we write about items that are a part of one of our affiliate partnerships and we will get a percentage of the revenue from sales.