Taking Your Office Attire From Day to Night

We only have one rule when it comes to planning a day-to-night outfit: Use versatile pieces.

But wait, why does this even matter you ask?

Scenario: You’ve got a long day ahead… Meetings, emails, conference calls, more meetings! Before you know it, you’ll be rushing off to that bar downtown for a night of carousing. So… What in the world should you wear???

On one hand, you can’t be showing up to work looking like a party animal, on the other, you wouldn’t want to fade into the background with your usual office garb at that hot new bar! To complicate things further, you can’t head home to change or freshen up due to time constraints.

We’ve all experienced this, at least once, and have probably caught a glimpse of well-dressed gents while we’re at it. A sneaky thought then slides into your head, disrupting your entire real-life conversation – “How is he so put together? Does he even have a job?”

Want to know his secret? Interchangeable outfits that will take you from “boss mode” to “life of the party” with a few simple tweaks!

Let’s walk you through a few quick tips.

What Should You Wear?

A Dress Shirt

Our top choice: A sleek dress shirt in white or blue; perhaps even a subtle print or textured shirt.

They’re extremely versatile, professional, and can easily transform into a smart-casual suave look that will keep you looking en pointe in the boardroom and in the bar.

When at work, you’ll want to look sharp and ready for battle – Refine your look with a tailored navy or charcoal sports jacket, and strap on a dimpled tie, preferably ones with subtle textures or prints so your ensemble doesn’t feel too flat.

Once you’re done for the day, throw out that tie, lose the jacket. Pop those top buttons and roll up your sleeves. These simple steps will transform that stiff dress shirt into a casual, relaxed shirt with a flattering fit, so you’ll be ready to party.

Always had trouble rolling your sleeves? Here are some basic techniques that are really easy to master:

A Polo or T-Shirt

Here’s an item every guy is sure to have in his wardrobe.

If your workplace is pretty chill, or practices dress down Fridays, you’ll probably pull off wearing a t-shirt to work.

Tees are a no-brainer when it comes to looking set for a couple of drinks and partying, so let’s not go there. What we’ll tackle instead are tricks to style up that tee so you don’t look too sloppy for the office.

Throw on a well-fitted blazer in Italian Wool (or wool blend), style your hair back to form a loose Pompadour, slap on a cool timepiece and maybe even tuck a pocket square into that breast pocket for a nice finish. You’re guaranteed to look way better than most men along the CBD.

Question of The Century: Are Jeans Ok?

We often spot men in a blazer + dress shirt + jeans combo. Are we a fan? To be honest, not really.

Who wore it better? Tailored Trousers VS Jeans

We’re not saying it’s wrong, sure you can… if practicality is what you’re after. But we really want to help you look jaw-droppingly good and pull off that Italian “sprezzatura” look, so we say opt for a pair of tailored trousers instead. Trousers are well-finished, have a proper fit, and are key to achieving a clean silhouette that would give you a more sophisticated look.

We highly recommend going for Navy, Grey, Khaki, or even Olive trousers for an office-to-party look. They are not over-the-top-serious neutrals, so they’d be really easy to work with, and are almost fail-proof.

Shoes & Everything Else

You’re in it for the long haul, so you’ll NEED something that’s comfortable and easy to walk in.

Our top 2 choices: A fresh pair of white leather sneakers, and fancy tassel loafers for a smart-casual look.

White sneakers are like a breath of fresh air to a typical shirt + trousers get up; a suitable choice for techies, and younger or fashion-forward men. You will never get tired in this if you’re going to be on your feet all night!

But, if you’ve got an important meeting in the day, you might want to opt for a sleek pair of loafers instead. They’re hands down, the dressier of the two and would complete a “no-nonsense” look without being boring.

Socks are another a great way to add a touch of personality and pizzazz to your looks. Go for a clean, simple look – hidden socks, or ones in solid neutral colours, to show you mean business. Evenings call for something a little more fun and creative, slip into a pair of bold coloured or patterned socks to make your outfits pop.

Now you look all set to party! But, do you smell ready? Another thing you can switch up is your cologne.

It’s always good to have a few different fragrances ready at your desk. Once your day scent fades, spray on your night-time cologne before you hit the road. Why is this important? With a night of partying comes a night of close encounters. You wouldn’t want to smell like you’ve just finished a 42km marathon, would you? So why not announce your presence with a captivating scent!


It’s safe and easy to stick to neutrals to accomplish a well put-together day-to-night look, but sometimes, special occasions call for a special look. Why not treat every night like one? You’ll never know who you might bump into, so don’t be afraid to play around with prints and colour for a memorable look.

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