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Chukkas are the business casual of boots; They’re unpretentious and comfortable, yet look sharp enough for most social occasions where you’re trying to make an impression on someone that you’re not a slob who exclusively wears worn-out sneakers to the bar. Not only are they tremendous shoes for a date or hitting happy hour on a Friday and Saturday night, but if you’re a professional 9-to-5 cubicle monkey chukkas look great with khakis or jeans in an office environment. Plus, their availability is pretty widespread these days, with almost every serious shoemaker having a couple of leather options with varying price points in their men’s lines, such as: Red Wing, Sperry, and Cole Haan, along with now-ubiquitous classics like the Clarks Desert Boots.
Loafers
Sperry
A solid pair of loafers are shoes every man needs. They’re best if you’re an office jockey who needs semi-formal outfits at work to keep HR off your back. Leather driving loafers (or mocs) are just as comfortable as a solid pair of boatshoes without giving off the “I’d-rather-be-tossing-the-lax-ball-on-the-fratcastle-lawn” vibe. Some come with tassels, some come with buckles, and some are just plain leather. You do you when it comes to ornamentation. Anything you can keep clean and slip in at the start of your work day gets the job done.
Work boots
Red Wing
In college, I learned the value of proper work boots working while working at a tree nursery. When working 10-hour days lugging 150-pound balled and burlapped trees around you learn very quickly how important ankle stability, toe protection, and proper traction is. Like a knight’s armor, you want a pair of boots in your arsenal so that you, a.) can rough up and get as dirty as possible without giving a shit, and b.) can drop something heavy on your toe without fracturing any bones. Proper sole traction for digging your feet in the ground and not slipping is also a must. Even if you only use them every now and then, every Bro needs boots that are work-site ready; you never know when your buddy is going to ask you to help him replace a deck, dig out that koi pond, or lay a brick patio. Stick with the classic work boot brands: Carhartt, Wolverine, Danner, Red Wing, Timberland, etc.
Dress boots
Visual Amor/Tumblr/Pinterest
Dress boots are shoes every man needs. Just because you drive a Ford F-150 doesn’t mean you can’t appreciate the refined machinery of a Ferrari. You’re not always going to be playing in the mud. Boots are high fashion these days, so have a pair of leather ones around that you can throw on for going out in the cold weather months. Treat them meticulously with mink oil and leather conditioner like the badass pieces of fine-crafted footwear that they are and these shoes every man needs will last longer than most relationships.
Duck boots
Instagram/LL Bean
Wet feet suck. Wet feet are, arguably, the worst thing in the world. Wet feet are worse than Carrot Top.
And unless your dress leather boots have the Gor-Tex treatment, your toes are going to get wet fast if you’re trudging around outside on a slushy day. Thank God for duck boots, the shoes every man needs. Water-proof rubber boots are pretty much a necessity if you live in the Northeast, where dreadful grey puddles on street corners after snowstorms practically become their own bodies of water. Thanks to high demand, there’s a waiting list for the classic L.L. Bean Duck Boots, but there plenty of other muck boot options in the marketplace.
Gym sneakers
You’re a Bro. You lift. You get your minimum three days a week of cardio in. You play intramural or post-work sports. As self-explanatory as it comes, you need sneakers you can sweat in, even if it’s just for that coed kickball league you reluctantly joined for the happy hour specials. You keep your gym sneaker game fresh at all times. You look forward to those trips to Foot Locker to replace these more than you do trips to the gym itself because they’re shoes every man needs.
Casual street sneakers
Instagram
New Balance. Keds. Vans. Old school Adidas Sambas. Whatever. These are your go-to’s. These are the Ford Taurus and Toyota Camrys of shoes; sturdy, reliable, comfortable….sneakers you keep for casual day-to-day use, like running to the grocery store or going to get your car’s oil changed. These are the shoes you teach your dog how to fetch because you don’t really care if Fido’s teeth roughs them up a little bit — that just adds to their character. Built for comfort, not for speed, these kicks last for years simply because you refuse to ever throw them out. You justify keeping them in the closet simply because you’ll always have a lawn to mow.
Flip-flops
It’s a truly great Bro dilemma: Rainbows or Reefs? Both are excellent, high-quality flip-flops for bumming around the beach in the summer, but Bros tend to throw their allegiance behind one one brand of flip-flop. But forget the Rainbow vs. Reef rivalry for a second: Every Bro needs an open-toed shoe that makes using a urinal in a bar a slightly harrowing experience. Wearing flip-flops during the summer means feeling the sprinkles of your own piss as it hits the the tops of your feet when you take a pee at a bar. For this alone, I’m decidedly #teamreef. It weirds me out to have a pair of suede/leather flip-flops marinate in the urine that accumulates on bar bathroom floors. I need a flip-flop I can wash off and dry.
But whatever you do, don’t be the Bro who buys the novelty flip flops with a beer bottle opener on the bottom. If you can’t open a beer bottle any other way besides using a shoe that’s made contact with piss-filled bathroom floors (i.e.: the age-old lighter trick), you’re a fucking poseur Bro.
Chaco/Tevas/Keens/Birkenstocks
This is probably the only shoe on this list that isn’t 100% a necessity, but if you’ve never spent a summer with your foot wrapped in a comfort of a non-flip-flop sandal, you have no idea what you’re missing. For a varity of reasons, these are the ultimate summer shoe and a shoe every man needs. If you like jumping in and out of the water like a river rat during the summer (for, say, fishing or kayaking or even jumping off docks), these are a necessity; Flip-flops come off your feet too easily in the water and stepping on jagged, submerged rocks can ruin a fun afternoon.
The exception here is Birkenstocks, the German luxury sandal that you don’t really want to get wet. The only reason I’m lumping them in here is because last year I found out they’re making somewhat of a cultural renaissance after years of being the butt-end of jokes about stoner hippies who hang out in the parking lots of Phish shows. Birk on, heady older Bros.
Slippers
LL Bean
The first thing you put on at night and the last thing you take off. Keeps your toes nice and toasty during the long, hard winters. Don’t walk around your house or apartment a neanderthal, exposing your foot fungus to the people you live with. Plus, are you even really a true Bro without a clutch pair of suede moccasins or terrycloth scuffs? These are the shoes your girlfriend steals to wear. Replace them regularly ’cause they can get NASTY with foot sweat.
Boatshoes
What, you read this far and didn’t think we’d mention boatshoes as shoes every man needs? Please. This IS BroBible, after all.
One of the greatest joys in life is wearing leather shoes without socks. It is a wonderful, wonderful sensation. A timeless, classical look that matches with pretty much anything, boatshoe season to a true Bro never truly ends. It’sa timeless look many-a Bro’s grandfather mastered over half a century ago, when Eisenhower was president and milk was delivered to the back door.
If you wear boatshoes with the same frequency that I do (pretty much every day, late-March – mid-October), expect to go through at least two pairs a season. Even if you’re buying the best pair money can buy (*cough — Sperry Gold Cups — cough*), you’ll wear them out pretty quickly if you do a lot of walking. Be careful about the lack of arch support. If you wear boatshoes on the daily (and what Bro doesn?), memory foam shoe inserts can be pretty clutch in making sure you don’t screw up your feet over time.
Black leather dress shoes
Ebay/Buzzfeed
Attending weddings, funerals, achievement banquets, and retirement dinners is just a fact of life. There will always be one reason or another that you’ll need to wear something formal. Despite what all the glossy men’s magazines say about luxury dress footwear, you don’t have to buy upscale designer hand-stitched Italian leather to look presentable. If you’re only throwing on black dress shoes a couple times a year, something off the rack for $50 looks perfectly fine.
10:48 PM
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