Dressy Casual Men’s Attire: What It Is & 10 Ways to Nail the Dress Code

If you feel out of your depth with a dressy casual assignment, don’t worry. More often than not, it feels like dress codes are there to stump us. Get to the bottom of what dressy casual attire for men looks like and feel confident when picking out your next outfit.

Dressy casual attire is all about subverting both of the styles (dressy & casual) with unexpected pairings. You can take an informal article of clothing (shorts) and upscale it with a luxury accessory (patent leather shoes) or dress down a formal suit with an informal tank top or t-shirt.

Mens dressy casual attire isn’t so strict that there’s no room to play around. You’re only limited by your imagination when it comes to putting together a dressy casual outfit. And once you create a few winning combinations, you’ll be able to notice one from a mile away.

Dress codes are difficult enough on their own when they’re hyperspecific. Throw in a hotly debated dress code like dressy casual and you’ve got a nerve-wracking assignment on your hands. You can rummage your closet for hours hoping to cobble together a suitable outfit, or you can nail the brief with one of our favorite dressy casual outfits.

When it comes to clothes, tailoring makes all the difference. Any clothing item that fits neatly to your frame will immediately elevate it. Want to take a simple winter overcoat into something more dressy? Get it tailored.

Pair it with a standard button-down and window pane pants (or whatever pattern you prefer) and you’re ready to seize the winter wonderland in your dressy casual outfit.

Mens suits are staple wardrobe pieces because you can dress them up or down. Avoid vests if you’re going for something dressy casual as they take it to a formal event level. Instead, dress down your favorite suit or slacks, button down, and blazer with a casual accessory.

If it’s an outdoor event, sunglasses give off an effortlessly cool vibe that keeps your dressed-up outfit from being overly dressy.

Related: 8 Tips to Help Anyone Rock Business Casual Jeans at the Office

Mixing casual and formal fabrics is an awesome way to make do with what you’ve got. There’s no reason you have to buy an entirely new outfit for a dressy casual event. Rather, think of mixing fabrics together to instill that casual flare.

A linen blazer paired with a smooth rib knit turtleneck is unexpectedly lush without feeling too ostentatious. An everyday cool weather top with a summery business staple creates a lovely dissonance that reads dressy and casual simultaneously.

If you feel more comfortable sticking to the standard pieces (slacks, overcoat/blazer, and top), then branch out with an interestingly patterned overcoat and some fun accessories. Dressing down your average business outfit is as easy as slapping a newsboy cap on your head and an interesting coat over your shoulders.

Another unique way to play with the dressy casual brief is with sizing. A finely tailored suit will always read formal, while a slouchy oversized suit or blazer rings more casual. Pair it with a simple t-shirt to further push your outfit into the casual category.

If you’re not a fashion-forward kind of guy, then you shouldn’t mess around with too many layers. Now’s not the time to make things more complicated than they need to be. Instead, stick with the dressy casual poster boy outfit — a nice sweater and a pair of slacks.

Related: Our Fave Casual Clothes for Men Over 60

Heading to an event that’s more on the casual side of dressy casual? Time to break out the jeans. When paired with the right pieces, jeans can be elevated into something quite professional. A nicely-fitting white button-down and a statement belt will take the blue-collar staple from the farm to the reception table.

Low on time and scrambling to put a dressy casual outfit together? Monochrome tops and bottoms always give off a put-together attitude. Even a mock turtleneck and a colorful pair of pants can work in a dressy casual setting when they’re in the same color palette.

Similarly, throwing a contrasting colored cardigan or trench coat will add to the overall refinement without sending it straight into wedding territory. And you can add a little flash with a big piece of jewelry, like a gold chain, if you're feeling spunky.

If you’re a more fashion-forward kind of guy, then you may want to pull from past catalogs with your dressy casual outfit. Take a page out of early 1960s aesthetics with unbuttoned bowling shirts over tanks, but pair them with professional trousers and a belt.

This is perfect for people with a more renegade outlook on fashion. Sometimes you want to stand out and push the dress code boundaries, and this one takes it right up to the limit.

Dressy casual attire isn’t an exclusively cool weather dress code. For those summer events, pair pleated shorts with a colorful short-sleeved polo and clean sneakers. Depending on the event, you may want to dress it up with a nice belt and watch or dress it down with a fun hat and sunglasses.

Related: Garden Party Attire for Men Made Easy

Sure, dressy casual is an oxymoron which makes it perplexing from the jump. But with the right guidance, you, too, can nail that dressy casual attire. Now’s the perfect time to dive deep into your closet and see just what you’re working with.