Dressy Casual in the Age of Athleisure Between attending operas and hanging out in basements

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 rest.

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

Chinos

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 lifestyles.

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 casual: 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 casual.”

Dress it up with: a shawl neck blazer and chinos
Dress it down with: jeans and rolled sleeves

Polo

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 casual: graphic tee
Too formal dressy casual: ruffled dress shirt

Dressy Casual Shoes

dressy casual shoe styles

Derbies

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 casual: 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 casual: denim jacket
Too formal dressy casual: suit jacket

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 era.
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.