Have you ever puzzled over what shoes to wear with that suit? Or whether to pick loafers or oxfords for a night on the town? Or whether brogues are all right for a wedding? Or even: what in the world ARE brogues?
Welcome. You are finally in the right place. Whether you’re a shoe aficionado, or just trying to cover your bases, this snappy guide to men’s shoes will make choosing the right pair simpler than you ever thought possible.
Men’s shoes 101: Lace-ups
The Oxford
What: Any lace-up shoes that expose the ankle.
Wear with: Can be formal or casual, depending on the type of leather and sole. A patent leather-soled version is great with a formal suit or tux. A full-grain leather topper and rubber-soled version pairs nicely with chinos or dark-wash jeans. And the thinner the soles, the more formal the Oxfords!
Balmorals
What: Oxfords drawn together by laces sewn under the front part of the shoe and then closed over its tongue. Looks like the shoe is made from one piece of leather.
Wear with: Suits and formal or semi-formal wear; won’t pair well with jeans and chinos.
Bluchers / Derby shoes
What: The lacing system is sewn on the shoe’s outside, with visible flaps. Plus, the sides of the shoe are sewn on top of the front part.
Wear with: Smart-casuals like jeans, dress shorts and sport coats; should be worn with a suit only on rainy days. Broguing, a split toe or color combinations make them more casual.
Brogues
What: Characterized by decorative perforations on the uppers, brogues can come in any shape of shoe or boot.
Wear with: The more broguing a shoe has, the less formal it becomes. So, a full brogue is perfect for jeans, chinos and other casuals; semi-brogues can be worn with a blazer or sport coats; and quarter brogues can be worn as a dress shoe with a suit. Never appropriate for black tie or white tie events.
Wing-tips
What: Toe broguing that resembles a bird with its wings spread.
Wear with: Jeans, chinos and other casuals. Opt for smooth or uniform leathers to make the broguing shine.
Men’s shoes 101: Slip-ons (see, no laces!)
The monk strap
What: Have a metallic buckle and leather strap instead of laces.
Wear with: Can be dressed down with cuffed jeans or dressed up with a dapper suit. Match the metal of the clasp to your belt buckle, wristwatch and cufflinks.
Moccasins
What: The soles and sides are made from one piece of leather. A fashion necessity!
Wear with: Wear through the day, switching from a business suit to clubbing jeans.
Loafers
What: Resemble a moccasin on top but have a wide and fairly flat heel. A more casual variant is the driving moccasin that has a softer, less structured look and a dotted rubber sole.
Wear with: Jeans, chinos and casual jackets; only wear with a business suit when traveling.
The opera pump
What: A formal loafer made from black patent leather, with a grosgrain ribbon decoration on the cap.
Wear with: Black tie or white tie ONLY.
Tassel loafers
What: Loafers with two tassels on each upper; strongly reminiscent of the ‘20s and synonymous with the classic mod look.
Wear with: Jeans and a sports jacket for a relaxed but upmarket look.
Penny loafers
What: A white strap with a diamond shaped cutout runs across the top of the shoe.
Wear with: Corduroy pants, chinos, flannel slacks, linen and seersucker.
Boat / Deck shoes
What: Canvas or leather uppers whose rubber soles have a herringbone pattern cut into them for added grip on wet surfaces.
Wear with: Casual summer shoes and should not be worn with a suit, blazer or sport coat; work well with slim, streamlined jeans, khakis, slacks or shorts.
Espadrilles
What: Trademark rope soles – real or faux. In the summer heat, the rope soles breathe without getting your feet dirty like flip-flops or sweaty and sticky like sneakers.
Wear with: They’ll take you from the beach, to the barbeque, to dinner.
Men’s shoes 101: Boots
Ankle boots
What: Standard low boot, with a leather body, rubber sole and rounded toe.
Wear with: Versatile: can be worn under suits in business settings, on dates or for special events.
Dress boots
What: Short, ankle-length boots with a slight heel and built like your standard Oxford.
Wear with: A sport jacket, odd trousers or dressy jeans; only wear with a suit in cold or wet weather. For the latter, opt for thinner soles and glossier leathers.
The Chelsea boot
What: An ankle-high boot with elasticated side panels that run from above the welt to the opening.
Wear with: Can add a classic touch to jeans, but also give a slightly alternative look to a tailored suit. Polished leather can be formal or casual, while suede ones are for casual to semi-formal outings only.
The chukka boot
What: Ankle-length boots with 2-3 pairs of eyelets with open lacing on each side. Not to be confused with desert boots, which have a casual rubber sole instead of the traditional leather.
Wear with: Can hold their own in semi-formal or business casual situations.
Jodhpurs
What: Ankle length, round toe and low-heeled shoes fastened with a strap and buckle that wraps around the ankle.
Wear with: Fitted chinos, jeans, casual suits and sport coats; don’t wear them with baggy trousers. DON’T tuck your jeans or trousers into them!
Hiking boots
What: Provide support above the ankle with a suede or leather upper, padded collar, and soft leather lining. Also have a cushioned insole, padded tongue and a thick rubber sole.
Wear with: Jeans and outdoorsy pieces – think chunky knit jumpers, Barbour jackets, tweeds and cords. A chunky sock, worn ruched at the ankle, will add a tough edge!
Workwear boots
What: Originally steel-toed, the new generation of workwear boots subs in a nonmetallic composite material without sacrificing the toughness.
Wear with: Casual, rugged attire such as slim-fit indigo jeans, worker-wear jackets, flannel pieces and chambray/denim shirts (think stylish lumberjack). Skinny jeans can make these appear clumpy and unsightly.
Biker boots
What: The height ranges from above the ankle to below the knee, but all motorcycle boots boast a low heel and heavy-duty leather.
Wear with: A classic leather jacket, a relaxed fit pocket tee and dark denim.
The cowboy boot
What: A tall boot shaft at least above the middle of the calf, no laces and a heel of about two inches.
Wear with: Jeans (preferably a dark and slim boot cut), an Oxford shirt and a tweed sport coat.
The military boot / Combat boots
What: Run the gamut from ankle-high to under-the-knee, and are made from technical materials like waterproof leather, Gore-Tex and rubber.
Wear with: Dark denim (with a couple of cuffs or tucked directly into the boot), a vintage tee and a tailored peacoat.
Men’s shoes 101: Open-toes
Thongs
What: Flip-flops
Wear with: They’re beachwear, plain and simple – don’t wear them with anything other than shorts. And never (ever!) wear with socks.
Sports sandals
What: Several wide cross straps that go over the foot for support. Also waterproof, with an athletic sole for traction.
Wear with: Jeans, shorts or chinos.
Dress sandals
What: A slightly more formal version of sports sandal, with leather replacing rubber and metal buckles replacing Velcro straps.
Wear with: Perfect for spring and summertime outdoor events and with linen suits. DON’T wear with socks. Please.
All illustrations by Kristina Hultkrantz
Awesome guide! I love brogues and chelsea boots them most