Classic Menswear: Casual But Elegant (Part 2 Of 2)

Previous episode, we shared how to dress for the more formal end of the spectrum. As mentioned, classic menswear stretches across a wide spectrum. So today, we’re gonna take a look at the dressed down side of it. We’re gonna explore how to still adhere to classic menswear, whilst dressing down with elegance. That’s right, you can remain elegant whilst dressing down in sporty attire.

Title page image showing the author, dressed in classic menswear, pointing to the title text.
Yes, you can remain elegant even when dressing down. And yes, I’m wearing a day cravat here. That’s a classic way to dress down an otherwise dressy navy blazer.
Image by Author

There’s A “Casual” Classic Menswear Too?

Contrary to popular belief, classic menswear covers more than just the formal side of the spectrum. So let’s explore the lesser known side of the classic menswear options. Today, we’re gonna learn how to dress down and get comfortable, but still remain elegantly dressed. And we’ll start with the dressiest of the classic menswear’s casual attire :-

(4) Business Casual – Still Business Appropriate

You don’t have any business meetings scheduled today. But what if you bump into a prospect during happy hours at the pub? Or perhaps you’re enjoying your favourite cuppa at your local Starbucks. What are the chances that your clients might drop in unannounced? Would you wanna engage in an impromptu business conversation with them in your “comfortable” clothes? What if you’re wearing a loud Hawaiian shirt, bright pink shorts and slippers?… Probably not… A better choice to bridge being casual and business appropriate is the business casual attire.

Elegant looking grey glen check sport jacket, pink OCBD shirt, burgundy chinos, "autumn colour" knit tie and bright red pocket square.
A dressy grey sport jacket in subtle glen check pattern, and a pair of burgundy chinos. A pink OCBD shirt with a knit tie in “autumn colours”. And don’t forget the fun pocket square.
Image by Author

The star of the business casual outfit is definitely the sport jacket. In a pinch, you can dress up a sport jacket with dress shirts and trousers. That’ll put you in a similar ballpark with the blazer. Swap the dress shirt and trousers with Oxford cloth button-down (OCBD) shirt and chinos, immediately you’ll look casually elegant. Throw on a casual knit tie, and voila, you’ve got a quintessential business casual outfit. Wanna dress it down even further?… Try the example below :-

Elegant looking grey textured and unstructured sport jacket, bold blue striped shirt, khaki chinos, houndstooth knit tie and low contrast pocket square.
Rough textured, unstructured, and unlined sport jacket, with hip patch pockets. A pair of khaki chinos, a bold striped blue shirt, a knit tie, and pocket square.
Image by Author

Swapping smooth for a more textured fabric brings down the formality a notch. Remove the shoulder pads and structured chest for a softer drape brings it down another notch. Then replace the flapped pockets with patched pockets to seal the deal in making this a casual sport jacket. Bonus point if you can keep the rest of the ensemble relatively low contrast.

(5) Dressy Casual – No Business, Strictly Pleasure

You’ve logged out of your office network, shut down your computer, and you don’t even wanna think about work anymore. You’re dedicating the weekend strictly to pleasure. Can you dress down your attire any further, and still look elegant? Of course, just lose the tie… Actually, it’s a little more complicated than that, but here are some examples :-

Elegant looking charcoal brown, flannel and unstructured sport jacket, denim shirt, khaki chinos and low contrast pocket square.
Unstructured and unlined, charcoal brown, flannel sport jacket, denim shirt, and the same khaki chinos from above. A gingham check pocket square, picking up the blue of the shirt.
Image by Author

Denim has the magical quality to turn anything it matches with casual. So choosing a denim shirt in your ensemble is a surefire way to achieve that. But throw a sport jacket over the denim shirt, and immediately you crank an otherwise casual outfit up a notch. Yes, you can make a casual outfit a little more elegant. And yes, you can leave out the tie. Open neck is the way to go if you wanna keep things casual.

Elegant looking textured and unstructured grey sport jacket, blue/grey roll-neck jumper, dark wash jeans, and low contrast pocket square.
Swap any button down shirt with roll-neck jumper, and you’ll dial the formality all the way down. Then match it with a pair of dark wash jeans to give it a casual but elegant look. And don’t forget the pocket square too.
Image by Author

Try swapping one denim piece with another. Replace the denim shirt with a classic pair of dark wash jeans. Then throw on a roll-neck jumper, and you won’t have to worry about exposing your neck. This is as low as you can crank your formality dial down, and still remain elegant. Any lower, and you’ll cross over into the “just keep it casual” zone… But what if you really want to do that, and still remain elegant?… Is it even possible?… Well… Kinda…

(6) Just Casual – But Is It Still Elegant?

Now, we’ve just ventured into the twilight zone of classic menswear. Time to break out your swagger. No more trying to look like a polished gentleman. You are who you are, and you don’t care if others like it or not. So here are some examples of outfit that might fit your bill :-

Tan coloured Harrington jacket, white Polo shirt, and medium wash jeans.
A neutral tan Harrington jacket, over a white Polo shirt, and a pair of vintage medium wash jeans.
Image by Author

You may be wearing an ordinary ensemble of Polo shirt and medium wash jeans. To nudge it up a notch, simply throw a jacket, any jacket, over your Polo shirt. Of course, it won’t elevate you up to the level of a sport jacket. But it’s still a notch higher than you not having any jacket on. You can choose a Harrington jacket, a bomber jacket, or even just an over-shirt. Anything to layer over your base Polo shirt.

Light wash denim trucker jacket, white t-shirt, and olive green jeans.
Denim trucker jacket, over a plain white t-shirt, matched with an olive green pair of jeans.
Image by Author

Nothing oozes with masculinity more than the classic trucker jacket, especially a denim trucker jacket. At this point, it doesn’t matter anymore what you match it with, as long as you keep things really casual. I wouldn’t exactly describe this ensemble as elegant… But man… it’s sure to make many a heart swoon, and knees weak… No matter how you look at it, the denim trucker jacket remains the statement piece here. Take it off, and you’ll end up looking like Tom from Accounts Receivable. Perhaps Dick from Pre-Sales, or Harry from Tech Support. In short, you literally become a nobody…

Still Classic, But Is It Still Elegant?

You may have noticed from the examples above, that elegance tapers off as you venture further down the formality spectrum. But as a rule of thumb, any ensemble with a lapelled jacket will always be elegant. Yes, even with the most casual, unstructured, heavily textured or patterned, sport jacket. And yes, even when you wear that over an even more casual denim shirt. Don’t get me wrong, you’ll still look masculine in a denim trucker jacket. You just don’t exactly project an image of a refined gentleman. And, they’ll probably deny you entrance to a jackets-required, fine dining restaurant.

So what’s your personal brand? Do you consider yourself an elegant gentleman? Or would you like to offer your own opinion too? Then leave your comments or questions below. And yeah, don’t forget to feed my caffein addiction too if you like this kind of content. It’ll help keep me awake enough to keep pumping out content like this.

This article is part of Espoletta’s CSR (Corporate Social Responsibility) initiatives.

Do you dress like an elegant gentleman?
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About CHOW Wei Ming

Brand consultant, photographer, creative director, storyteller, and a true believer of the power of visual communications. Outwardly expresses a friendly disposition, but hides a perfectionist nature deep inside him.

One Reply to “Classic Menswear: Casual But Elegant (Part 2 Of 2)”

  1. Pingback: Classic Menswear: Business Appropriate (Part 1 Of 2) - Espoletta

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