Discovery Quiz: What Shoes Should You Wear?

any outfit. Cover your footwear bases from dive bars to interviews

by Janet Hu
image by Michelle Tirronen, Studio]
We’ve always found that
punchline in Legally Blonde–the supposed statute that only gay guys know shoe
brands–a little unjust. In reality, all men can appreciate good footwear.
Shoes have a huge impact on
your presentation, in how tied together your look is. And you can bet that if
you wear the wrong shoes, a.k.a. combat boots or slippers with a three-piece
suit, more than one person is going serve some side eye.
But that’s obvious. How about
the less glaring options on an everyday basis?
Tired of wearing the same
sneakers day in and out? Unsure of how to dress for a Black Tie event?
all results for what shoes to wear:
A standard classic when it
comes to dress shoes. Oxfords have closed lacing and can be worn with anything
from jeans to dress pants.
This sophisticated but
laidback footwear provides a slim silhouette that hugs the foot’s contour.
Oxfords can be leather or suede and adorned with ornate stitching (or not).
Similar to Oxfords, Derbys are
great smart casual shoes. They have open lacing, making them a bit less formal
than other dress shoes.
Derbys were originally
intended as sporting and hunting footwear in the 1850s, but now, they pair well
with rolled jeans or chinos.
These moccasin-inspired shoes
are embraced for their slip-on style. Though casual and comfortable, they still
signal an element of style consciousness.
Loafers originated as royal
house slippers for England’s King George VI, but by the 1960s, American lawyers
and businessmen were wearing them with suits. You can wear loafers with
anything from shorts to a casual suit.
These non-lace ankle boots
popularized by the Beatles are a savvy classic.
Fashionable and minimalistic,
if you own just one pair of men’s boots, they should probably be Chelseas. Wear
them with chinos or dark jeans and a blazer for a night out.
These ankle-length casual
boots are made of leather or suede and have fewer eyelets than dress boots.
Desert boots are perfect with
rolled pants, relaxed button-downs, and smart casual jackets. They have a
slight combat edge to them, but they’re far less heavy-duty than workwear
These shoes from the Victorian
era are the most formal of all dress shoes. Opera pumps were traditionally worn
in the evening for dances, operas, and other social soirees.
If you’re dressing to
impress–like, really impress–then go for Opera pumps. This footwear is only
suited white or black tie events.
Opt for dress boots if you’re
wearing a winter suit, or if you just want to demonstrate first-rate style.
The beautiful thing about
dress boots is how versatile they are. From cap toes to wingtips to various
other stitchings and perforations, you can go smart casual or formal.
Commonly worn by boaters and
non-boaters alike for both form and function, boat shoes have become a classic
in men’s footwear.
They’re refined and sporty,
all in one. Wear boat shoes with anything from shorts to chinos, but make sure
you’ve got on no-shoe socks.
Strap Shoes:
These dress shoes are
classified as unique, definitely dapper, and a little old-timey.
The Monk strap shoe sits
between Oxfords and Derbys in terms of formality. They’re practical and dressy,
and a little rarer.
High Tops:
The original cool, edgy,
on-the-go sneaker, Chuck Taylors will never go out of style.
Through wear and tear, through
skateparks and trendy lunch meetings, and everything in between, you can
incorporate a beloved pair of converse into almost any outfit.
Athleisure and luxury
sportswear are hot.
Whether you’re wearing chinos,
tapered sweats, or even a suit, top off your outfit with an edgy pair of
athletic shoes. Look coincidingly streetwise, and business savvy, and like the
life of a party.
Workwear is very much late
2010s. Inspired by streetwear, boots like Timberlands and Doc Martens exude
that edgy, modern, semi-grunge style.
Workwear boots are typically
heavy-duty, with laces and thick rubber soles. Wear them with distressed denim
and long overcoats.
So, what shoes will you go
with? Feel free to post photos of your complete look in the comments below


Kayode Ojo
Kayode Emmanuel Ojo is the Co-Founder and Managing Director at SHEFFA Limited. He is presently studying Computer Science at the National Open University, Victoria Island, Lagos.