Dressy Casual in the Age of Athleisure

Between attending operas and
hanging out in basements

Written by Janet Hu

Did you wear sneakers to work
this week? For many of you, that’s a “yes.” And for some of you, that’s a “heck
yeah, I wore sweatpants.” In the age of athleisure, one sometimes feels out of
place in suit and tie. But is it a crime to look sharp? No, not at all. Here’s
a guide on how to be dressy casual, or smart casual, to look a cut above the

What is dressy casual?

Dressy casual is ultimately
casualwear. You wouldn’t wear a dressy casual outfit to an event that calls for
semi-formal or cocktail attire. These snazzy parties require a little more
frill. You also wouldn’t sport dressy casual to a job conference that requests
business casual. Remember that it never hurts to look nicer than average, but
it does hurt to be underdressed for a formal or professional event.
This particular style, dressy
casual, is in between operas and hanging out in basements. It’s meant for daily
wear so that you can look dapper out and about.

A few dressy casual elements,
and how to incorporate them:

The following clothing items
are considered dressy casual. However, it depends on how you pair them. Any of
these can become very casual or quite formal when worn with other elements on
the formality spectrum.
Dressy casual pants

                     dressy casual pants

The quintessential dressy
casual pant. Made of tightly woven cotton, Chinos have a straight silhouette
and smooth finish. They’re also soft, have a lot of mobility, and come in a
wide array of colors. These pants aren’t fit for professional offices, but they
can be worn to nice dinners and even horse races when appropriately styled.
Dress them up with: a
button-down and oxfords
Dress them down with: a
graphic tee and converse

Commuter Pants

Where workwear meets
professional wear. Commuter pants are a godsend. They resemble suit pants with
their pleating and sophisticated fabric finish. However, as their name
suggests, they’re also made with stretch fabric and intended for active
Dress them up with: a mock
neck sweater and chukka boots
Dress them down with:
basketball shoes and a hoodie
Dark Wash Denim

Denim is inherently casual.
It’s a sturdy cotton twill worn originally by blue-collar workers and coal
miners. And distressed denim today still holds all the same rugged badassery
that it did during the Wild West era. Dark wash denim, however, can be chic. As
a general rule of thumb, darker colors exude a more formal air. Jeans will
never be acceptable at a wedding, gala, or business meeting, but dark wash
denim with a pair of derbies can make you one of the best-dressed men at MoMA.
Dress them up with: Chelsea
boots and an unstructured blazer
Dress them down with: drop
tail tee and workwear boots
What’s Not Dressy Casual

Too casual to be dressy
track pants
Too formal dressy casual:
dress suit pants
Dressy Casual Tops

                             dressy casual top styles
Chambray Shirt

The archetypal casual
button-down. A classic, but a goodie, that has all the structure of a dress
shirt: collar, cuffs, yoke. Chambray is a semi-formal fabric of soft brushed
denim. It’s similar to flannel but a little less fluffy. Makes sense why this
folksy textile constructed into a formal dress shirt would be exactly “dressy
Dress it up with: a shawl neck
blazer and chinos
Dress it down with: jeans and
rolled sleeves

Worn traditionally by
equestrians at horse races, polos have always had a sporty, preppy reputation.
With a sturdy collar and structured fit, they possess the formality of a
uniform. But these tops remain rightfully in the dressy casual sector due to
their short sleeves and athletic design.
Dress it up with: a trench
coat and Chelsea boots
Dress it down with: shorts and
boat shoes
Knit Sweater

Knit sweaters effortlessly
connote artfulness and sophistication, especially those woven from high-quality
wool. If you add a mock neck into the mix, you’ve achieved Jackson Pollack
level elegance and finesse. Cozy sweaters won’t replace the power suit, but
they are perfect for elevated casualwear.
Dress it up with: an
unstructured blazer and chinos
Dress it down with:
wide-legged workwear pants and beanie

What’s Not Dressy Casual

Too casual to be dressy
graphic tee
Too formal dressy casual:
ruffled dress shirt
Dressy Casual Shoes

                            dressy casual shoe styles

Derbies are a less formal
version of Oxford dress shoes. This is due to their open-lacing, which allows
for a wider fit. These shoes originated as hunting boots in the 1850s, but they
are now commonly considered dress shoes. With its lace-up style and leather
makeup, derbies are a perfect candidate for a smart casual outfit.
Dress it up with: commuter
pants and a button-down shirt
Dress it down with: shorts and
a vintage tee
Chukka Boots

These ankle boots originated
as polo sportswear. Made of leather and being lace-up, they can be worn with
casual suits. These shoes are unadorned, unlike other dress boots, which
sometimes have cap-toe or wingtip perforations. The desert chukka boot has a
rubber crepe sole and presents more combat-y vibes.
Dress it up with: dark denim
and an unstructured blazer
Dress it down with: distressed
jeans and a v-neck tee
Chelsea Boots

Originating from Victorian
England as a reimagined riding boot, the Chelsea boot has dapper in its DNA.
It’s also designed to be easily slipped on and off as an active and minimal
men’s boot. It will remain trendy and modish, thanks to being famously worn by
the Beatles, but Chelseas have never been a component of formal wear.
Dress it up with: pleated
pants and pea coat
Dress it down with: colorful
chinos and a jumper
What’s Not Dressy Casual

Too casual to be dressy
athletic sneakers
Too formal dressy casual:
opera pumps
Dressy Casual Outerwear

                             dressy casual jacket styles
Unstructured Blazer

The unstructured blazer is
sexy. It’s relaxed but swank. The lapels and overall formal design make this
jacket look clean and sophisticated. The fact that it has a natural fit,
though, with no shoulder pads or stiff wool components, makes it much less
staunch than officewear. In addition to smart or dressy casual, unstructured
blazers are also appropriate as cocktail attire.
Dress it up with: pleated
commuter pants and oxford shoes
Dress it down with: dark denim
and converse high tops.
Shawl Neck Cardigan

How comfortable yet elegant.
The shawl neck sweater allows you to feel warm and cozy during winter months
without going full Columbia sportswear. The semi-ornate neck adds a touch of
formality, so you’ll look ready to swig oakey bourbon by a fireplace, as
opposed to hot chocolate at Starbucks.
Dress it up with: button-down
shirt and dress pants
Dress it down with: colorful
chinos and workwear boots
Trench Coat

The trench coat is
exceptionally versatile. With the formal structure of notched lapels, belt, and
a double-breasted front, these coats have an upscale look. However, being made
of durable, often water-proof fabric, and having many pockets, the jacket
resembles utility wear a little more than it does formalwear.
Dress it up with: a suit
Dress it down with: a v-neck
sweater and jeans
What’s Not Dressy Casual

Too casual to be dressy
denim jacket
Too formal dressy casual: suit
Dressy Casual Accessories

                        dressy casual accessories
Knit tie: a little less
formal, and a little more unique, than your typical silk tie. Knit ties are
perfect to wear with sweaters and shawl neck cardigans.
Men’s scarf: a splash of style
and sophistication. There are many ways to wear a men’s scarf in varying
degrees of formality.
Simple watch: classic ornate
wristwear that emphasizes your care for detail. Though not as flashy or
eye-grabbing as a precious metal or jewel-encrusted watch.
Men’s bracelet: similar to the
wristwatch, this piece is there for a flash of embellishment. Men’s jewelry, in
general, defies stuffy convention. Go with a nice beaded bracelet for dressy
casual, as opposed to a solid gold or silver one for formal events.
Novelty lapel pin: add a
little spunk and personality to your outfit. Lapel pins don’t have to be reserved
for ultra-formal Black Tie events. Wear a mustache pin on the lapel of your
unstructured blazer and invite a little flattery.
Overall, dressy casual is a
grey area with a lot of flexibility. And that freedom is fun. Blend aspects of
high fashion formalwear with the comforts of fast fashion, so you can master an
elevated edge without feeling completely out of place, or from a different time

As a tip, mix formal,
structured fabrics like wool and leather with soft and pliable ones like
cotton. And play with sizes. Any formal design becomes edgier and more
appropriate for daily wear with a looser fit.

Janet Hu Editor of The GentleManual

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.