There are a few things every guy has to have covered when it comes to their wardrobe. Staples like a great pair of jeans, a well-tailored lightweight wool jacket & the classic oxford all come to mind, however we can’t tell you how many times we’ll see a guy get it all right head to shin, only to fuck it all up with some pair of awkwardly proportioned square-toe-sneaker-hybrids. A mystery to us, we can’t figure out why a guy would kill his game with shoes that look best shoved back into the box they came in. It’s not as though there aren’t enough timeless, iconic styles out there. Dozens, really. Certainly enough to keep just about any guy covered anytime, anywhere so we’ve enlisted BKLYN Dry Goods family & #menswear enthusiasts, Bradley Gee & Nicholas Goode to let us in on some of menswear’s most iconic styles — styles that have since spawned a million incarnations & a million more knock-offs; styles that should easily take you from Gerber to grave. Sure, we know we’ve omitted some classics like Birkenstock’s Boston or Alden’s plain toe blucher — but we had to keep this list to just 10. Honestly, we know there’s no way in hell we could keep your attention for anything beyond that.

The Bean Boot, L.L. Bean (1911)

L.L. Bean is the king of kings in the catalogue shopping sphere. Yes, we frequently get frustrated when those glossy pages jam up our mailbox month after month, but we would never deny the influence Mr. Leon Leonwood Bean (doozy of a name no?) and his Maine-based company have had on the world of outdoor sporting goods. The mammoth flagship store in Freeport stocks everything from kayaks to alarm clocks, all printed with the iconic L.L. Bean logo, but the company had humble beginnings which centered around a single, exceedingly well-made, unintentionally stylish boot. First designed by Bean in 1911, The Maine Hunting Shoe is part rubber work boot and part leather hiking boot. Dry and comfortable, the iconic rubber bottoms stay the same, while the uppers come in a variety of styles (think calf-high, color, fur lined). Honestly, we think the originals still win out for the Maine moose-hunter or the Urban puddle-stomper; Summer thunderstorm or winter whiteout. They are made in America and have a lifetime guarantee. If you’re badass enough to wear out these rubber soles, send ‘em back to be repaired. No questions asked.

Chuck Taylor All-Stars, Converse (1917)

“Chucks.” They just about ooze classic-cool from every eyelet. High-top, low-top, red, white, blue or technicolor, Converse’s unisex canvas kicks have become a wardrobe staple. They are remarkably simple and instantly recognizeable. White rubber toe-cap, white stitching, simple canvas upper, meaty white laces, and a big star symbol right on the ankle. The beauty of the Converse style is its versatility. Virtually every popular subculture has attempted to take these shoes as their own – rappers and soccer moms prefer them fresh out of the box, punk rockers like them heavily Sharpied and studded, tweens dig them in neon and silver, and athletes…well, they wear them as well. As their proper name might imply, All-Stars were originally designed in 1917 by the Converse Rubber Shoe Company of Malden, Massachusetts as professional-grade basketball shoes. The company hired Mr. Charles H. Taylor to tour the country hosting basketball clinics and marketing the sneakers. The shoes gained popularity when they were introduced for the 1936 Olympic games in all-white with red, white, and blue trim, and were later used as trainers for GIs during WWII. In 1957 the low-top style was introduced, indicating that the brand understood that the shoe had become more than just a utilitarian trainer. They had become officially stylish. Sadly, Converse has since been bought out & the shoes are now made overseas. Try to cop a pair pre-’96 when the ubiquitous canvas kicks were still made in the USA or pick up a pair of All-Stars’ inspired Ethletic kicks — made in the USA & made with greater consideration of the environment.

Topsiders, Sperry (1935)

Founded by Paul Sperry in 1935, the avid boater was in need of better traction when on his schooner. He noticed that his dog had an excellent ability to keep its balance on slick, wet surfaces. He then examined his dog’s paws and used the blueprint as a reference in creating the soles of the first Sperry Topsiders, a style that lived pretty quietly among civilian sailors until the US Navy took interest in the non-slip style in 1939. WIth it’s well designed non-slip white non-marking sole — and a new military contract, The U.S. Rubber Company bought Sperry introducing the Topsider’s ingenious design to the masses. Whether your cranking a winch or pounding the pavement Topsiders break in quickly and form well to the foot so you’ll never have to worry about comfort. Like most great things, Sperry’s namesake brand used to make the Topsider in the United States & have moved production overseas, however we can’t ignore Sperry’s place in American sportswear. We just wish they were still made here. WIth that, the brand, keen on keeping it’s status as footwear icon, has been smart about partnering up with an impressive roster of brands like Band of Outsiders and J.Crew to help you look cool while keeping your cool during the hottest of summer heat waves.

Weejuns, Bass (1936)

In 1936 George Henry Bass, a boot maker from Wilton, Maine, began making a loafer modeled after a style he’d spotted during a trip to Norway. He called them “Weejuns” to acknowledge their Norwegian heritage, adding a signature leather band with a diamond cutout across the front of the shoe. During the 1940’s and ’50’s people began putting dimes in the diamond cut-out Bass had fashioned – the price of a pay phone call solidifying the styling choice. By the 50s & 60s., Bass Weejuns had fallen into favor amid the masses — from beatniks to James Dean. Dimes would later give way to pennies (the shinier the better) for aesthetic purposes, giving birth to the name, “penny loafer” — and by the 80s, Bass Weejuns (also now known as the Larson) had become a symbol of classic cool worn by everyone from JFK to Michael Jackson. The style, still hand-sewn remains as relevant today as it was 70 years ago — and since 2009, have been made in the Maine where the style was originally produced before production moved overseas for some time (we’re glad to have Weejuns’ production back on U.S. soil).

The Desert Boot, Clarks (1950)

Designed in Somerset, England in 1950 by Nathan Clark, Clark’s iconic Desert boot was inspired by the crepe soled boots worn by soldiers of the British Eighth Army in Egypt during World War II. Like some of our other top picks, Clark’s incarnation was simple, almost spare by design, ultimately complementing just about anyone’s wardrobe rather then competing with whatever it was worn with. Add to that, Clark’s dersert boot was lightweight, cool & surprisingly durable considering their comfort making the style an easy pick for gents for generations. Above all, they look so damn good. While the style itself hasn’t changed in over 60 years, production sadly has moved from Clark’s original Somerset factory.

Sambas, Adidas (1950s)

We turn to Adidas for another classic – The Samba. They were designed around 1950 to cater to the most popular sport in the galaxy, soccer. Playing the sport year-round required that players move indoors in the winter months, where cleats would not suffice. A sticky gumsole shoe helped give traction on hard or icy ground, and Sambas remained virtually the only indoor soccer shoes on the market for decades. Emblazoned with the classic Adidas stripes, these shoes have become fashionable on the street as well making their street wear debut during the 80s where they’ve kept a place in style history ever since. Keep them clean & dress them up with a nice pair of jeans and a buttondown, or let them get beat up and use them as your daily stompers. Oh, and they come in white as well, so they’re ready for all seasons.

#877/#875 Workboot, Redwing (1953)

Founded in 1905 in Red Wing Minnesota by Charles Beckman, Redwing’s first real iconic style wasn’t launched until years later. 1953 to be exact. While the near 60 year-old style seems to be known by most as a “work boot”, both the taller 8″ inch #877 & shorter 6″ #875 style were actually designed for sport, first popular among hunters & outdoorsmen. A bitch to break in, Redwings classic #877 & #875 later became a choice amid blue collar workers thanks to the styles sturdy composition & were later introduced to #menswear thanks to stylish city folk around 2003 — at the time we wanted to dress as though we’d all spent our days chopping wood or run around pretending we were all Steve McQueen who was a huge fan of the classic styles. Even better, the styles are 100% American made. Red Wing has been able successfully build their brand & business while keeping Minnesotans at work which is something we can all get into. Without compromising quality they have kept a huge fan base ranging from miners and ranchers, to city slickers and CEOs.

#44 Shoe, Vans (1966)

While it was originally Converse that designed the classic lace-up deck shoe, it was Vans who made the canvas style iconic. In the Mid-1970s, several important individuals from Los Angeles were revolutionizing the sport of skateboarding. They were known as the Z-boys of Dogtown, and they invented shred. Just a decade prior, brothers Paul and James Van Doren had opened a shoe company in Anaheim, and were producing simple canvas deck shoe with a sticky rubber sole that these skateboarders had adopted as the unofficial attire of their crew. As the skaters gained national attention, “Vans” rode the proverbial wave of popularity, eventually becoming one of the most important skate companies in history. While equally revered by preps along the Eastern Seaboard , the style remains the ultimate in slacker cool. I mean, Spicoli wore them in Fast Times in Ridgemont High. While Van’s first high top style, now called the Era didn’t make our cut, the brand’s first skate shoe, originally dubbed #95, designed by skate legends Tony Alva & Stacy Peralta in 1975, certainly deserve an honorable mention.

German Army Trainer, Puma & Adidas (1970s)

Perhaps the only shoe on our list that you have never heard of, the design of the German Army Trainer remains instantly recognizable. Brothers Adolf and Rudolf Dassler of Herzogenaurach, Germany opened a tiny shoe factory in the 1920s after returning home from the war. Operating out of their mother’s laundry room, the company remained virtually anonymous for more than a decade — until the Berlin Summer Olympics of 1936. The contentious Olympic games was nearly boycotted by the US due to its connection with the Nazi party, but after much debate, the US did send a team, which included runner Jesse Owens. The Dasslers were able to convince Owens to wear a pair of their track spikes to the games, where he won 4 gold medals. The popularity of the shoes exploded, however by the time World War II arrived, the brothers had a falling out, going their separate ways over a misunderstanding in 1943. “Adi” would then form the Adidas Shoe Company, and Rudolf would launch Rudo, later Puma launching a feud that’d last decades through the 70s when the brothers fought over a German Army contract to produce footwear for the troops. In the end, both Puma & Adidas produced to now storied style, the brothers each claiming the design as their own. The popularity of the shoe goes beyond its storied history, however. It is simply a phenomenal design that’s spare simplicity has since been copied by just about every designer from Hedi Slimane for Dior to Martin Margiela & has been rereleased as part of the Adidas Originals collection. If you can, we say find yourself a vintage pair & stick to the original.

Dunks, Nike (1985)

One really can’t the deny place in menswear history carved out by Nike Dunks. From its introduction in 1985 & surprisingly simply by design, Dunks (designed without Nike Air technology which was originally launched alongside Nike’s Air Force 1 in 1983) were originally designed (like the Air Force 1 for basketball. Soon, the focus was back on the Air Force 1 which served as inspiration for Nike Air Jordans after the brand scored a deal with a young Michael Jordan. It wasn’t until 1998 when Nike rereleased Dunks in a dizzying array of colors for university and college basketball teams. Old school styling, all those colors and much cheaper than Jordans, Dunks quickly earned a place amid skateboarders thanks to the low profile design of Dunks’ sole, later spawning Nike SB and specifically the Nike Dunk SB & has since been adopted hip hop royalty, streetwear heads & by the masses launching the style to cult status. Sure your Nike’s are probably made by some 8 year old in southeast Asia, but one can’t really challenge Dunks place among the ranks.