Men aren’t usually labeled as shoe addicts, but that doesn’t mean they aren’t capable of amassing a lot of shoes. (We see you, man with six pairs of dilapidated chucks left over from college.) To the shoe novice, the spectrum of mens shoes can be intimidating, and even if a pair seems perfect, there’s always the question of how it should be styled. In the interest of life simplification, we’re breaking down various shoe styles available for men. Not all shoes can be worn in all situations, but most can be dressed up or down to suit your needs of occasion, weather, time of day, an excuse to wear your new pink linen button-down and more. Check out the gallery with all of the outfits pieced together, and an explanation below.
Photo via Clarks
1. Spring Day Professional: The beauty of desert boots is that they make casual outfits look more deliberate, and give formal outfits more personality. Change up your suit look by wearing a pair of Clarks instead of your usual oxfords or loafers. They’re as old as the hills, so put your worries to rest if you’re hesitant about looking too trendy. Your dad probably owned them—ask him.
For: Your collaborative meeting at the coffee shop
Sweater: Our Legacy 50s Great Sweatshirt
Suit: Thom Brown Flannel Trouser, Thom Brown Flannel Sport Coat
Sunglasses: Warby Parker Winston
Shoes: Clarks Desert Boot
2. From Office to Pub: Don’t be duped by their name—desert boots are ideal for cold weather because they have a solid sole that will keep water and other riffraff from seeping through your shoes. This is an autumnal take on desert boots, for the British writer in you.
For: Your drizzly afternoon poetry-writing session followed by boozy dinner party
Sweater: LAD Jonathan Cashmere Pullover
Pants: J Crew Sun-Faded Oxford Chino
Coat: Revolve Penguin Peacoat:
Shoes: Oliberte Narivo
3. Warm Weekend Wear: With linen shirts and bright colors, desert boots can look so European Royal on a Yacht Trip to Ibiza. If you’re a lowly American commoner, you can still rock orange pants with your lace-up shoes.
For: Your Friday flight to Barcelona
Pants: Ben Sherman East End 14 Wale Corduroys
Shirt: J Crew Vintage Oxford Shirt
Scarf: Scotch & Soda Linen Scarf
Jacket: Scotch & Soda Washed Corduroy Blazer
Shoes: Clarks Desert Boot
Photo via Puma
1. Rebellious Preppy: Your summer uniform doesn’t have to be complicated. A light pair of pants, a good button-down, canvas sneakers, and a gin & tonic are all you need every day for a successful summer. Canvas sneakers are essential because they’re versatile and comfortable and, like gin, age doesn’t affect them! They look just as good straight out of the box as they will at the end of August when they develop that specific falling-apart charm that tells the world that you just had yourself a summer.
For: Your office booze cruise
Shoes: Converse Chuck Taylors
Khakis: H&M Twill Pants
Tie: Gap Textured Tie
Jacket: RVCA Night Shift Jacket
Watch: Daniel Wellington Classic Oxford
2. Comfortable Sophisticate: Sneakers have really grown up in the past few years. They add color and personality to your ho-hum everyday uniform, not to mention extra comfort if you’re on your feet a lot.
For: Your business day trip from Philly to NYC
Pants: 3Sixteen SL-120X
Shoes: Puma Suede Classics
Coat: Engineered Garments Baker Jacket
Scarf: Merona Grey Scarf
Bag: Tanner Goods Field Camera Bag
3. Creative Casual: This is a playful outfit that channels the teenage skateboarder of your youth, but the clean white shirt and khakis remind the world “I’m a responsible adult with excellent hygiene habits.”
For: Your summer as a freelancer
Shoes: Vans Liberty Era
Bag: Adidas Airliner Shoulder Bag
Pants: Levis Woodwork Jean in Khaki
Shirt: Scotch & Soda Constructed Workwear Shirt
Belt: H&M Leather Belt
Photo via Sperry
1. Relaxed Workwear: If you have one of those jobs with a standing desk and a well-stocked organic snack cabinet, you might be able to get away with sweatshirts and boat shoes in the office. You’re probably also going to live longer than the rest of us with your ergonomic lifestyle and work-life balance. Congratulate yourself with a new pair of Sperrys.
For: Your weekend overtiming at the office
Pants: Dickies Poplin Work Pants
Shoes: Sperry Top-Sider Original Boat Shoe
Sweatshirt: Tellason Crew Fleece
Watch: Union G-Shock
2. Outgoing Professional: Sperry Top-siders are the classic and come in a whole bunch of different colors. If you’re on board (boat joke!) with Top-siders but you’re hesitant about looking like a guy named Beckett who goes to yacht parties in Connecticut with his golden retriever, or whatever it is preppy guys named Beckett are doing these days, check out Sperry’s bright colors and prints. The brighter styles look good with florals and tropical shirts, but add a tailored blazer so you look more professional and less Little League Dad.
For: Your graphic design 9-5 in the summer months
Shoes: Sperry Top-Sider Barrel Lace Boat Shoe
Blazer: Scotch & Soda Tailored Blazer
Shirt: Stussy Aloha Button-Down
Khakis: Bonobos Khaki Pants
3. Effortless Hip: I get it, warm weather shoe-wearing is tricky business. Flip-flops are never ideal unless you are a teenage lifeguard. Boat shoes are the ultimate summer shoe: comfortable like sneakers but are classier for work. Plus, they’ll keep your feet cool and ensure that you’re always ready for a spontaneous stroll on the dock. Many guys would pair a casual outfit like this with sandals, but I suggest the boat shoe upgrade.
For: Sunday brunch followed by an urban hike
Jeans: APC New Standard
Glasses: Lookmatic Ricky
Shirt: Vans Guilder LS
Hat: The Quiet Life Floral Snapback
Shoes: ASOS Boat Shoes in Batik Print
Photo via Billy Reid
1. Not Trying Too Hard Dressy: Monk straps are the dressiest dress shoes in the game, but you don’t have to feel like your dad in them. Switch out your button-down for a henley and your chinos for jeans, then take the look up a notch with leather monk straps. Throw on a jaunty tie or pocket square for unfussy elegance.
For: Your date at the candlelit whiskey bar
Shoes: Billy Reid Double Monk
Jeans: Levi’s Made & Crafted
Henley: H&M Henley
Jacket: Billy Reid Dunnavant Jacket
Pocket Square: J Crew Chambray Pocket Square
2. Ambitious Academic: If you take your work (but not yourself) seriously, stay on your game and step up your daily uniform with well-made basics and a solid pair of dress shoes. If I met a guy wearing monk strap shoes as part of his daily uniform, I’d hire him immediately. For something. Anything. I’m not a hiring manager; that’s okay, I’d become one, just so I could hire a guy wearing monk strap shoes.
For: Your grad school seminar on the German literary tradition
Pants: J Brand Kane
Cardigan: Lacoste Buttoned Wool Cardigan
Shirt: J Crew Selvedge Utility Shirt
Tie: Hill-Side Tie
Shoes: Kenneth Cole Dining Room Loafer
3. Cool To the Nines: The witty contrast of a flashy print with black leather looks bold and self-assured. A bomber is a confident alternative to a blazer for evening events that don’t require a suit.
For: Your gallery cocktail party
Shirt: Sons of Heroes Jungle Tee
Pants: All Saints Chino
Shoes: Suit Supply Black Monk Strap
Watch: Watch: Seiko Military Watch
Bomber: Topman Bomber
Bag: Jack Spade Fulton Leather Darrow Brief