After-Work Drinks? Here's What to Wear
How to dress for both work and play with one outfit.
By: Logan RossDate: 2025-04-28
“Work hard, play hard” is a mantra many of the modern office-going workforce can abide by. Once the working hours are over, it’s time to relax and recharge; and every so often, the most recuperative "playtime” is actually that spent with those you work alongside.
Who doesn’t value off-the-clock (and off-the-record) conversations with coworkers at a nearby (or very far away) third-party establishment, when the uninhibited flow of drinks and conversation cathartically correlate?
Heading straight out from the office ensures your colleagues and confidants save on both travel and time: the only caveat — what does one wear?
Don’t fret, follow our experienced advice on how to appear professional from nine to five and personable from five to... late, all without requiring a change of wardrobe.
Let’s get to business first, shall we? A sports jacket is already the workhorse of your work wardrobe and can be paired with anything from tailored trousers to jeans, depending on the day’s agenda. Naturally, a sports jacket is perfectly at home at the office, though the right one won’t look out-of-place at the pub either.
The key is to keep it casual — opt for a soft or unconstructed interior (no stiff padding or structured shoulders), which offers a more laid-back appeal. As for colour and fabric, a solid navy or grey is the safe option, though pattern imparts a little more personality while bringing things down a notch in formality.
The great thing about wearing a sports jacket is that it allows you to cheat a little with what’s underneath. If you’ve got a jacket on, you can forgo a dress shirt and instead reach for something a little more comfortable and casual. In this case, an elevated knit like a crewneck sweater or long-sleeve polo works well without dropping the ball in the boardroom.
By the time you get to the bar, if you feel the need to remove your jacket for whatever reason, you can rest easy knowing you’re wearing a sweater below.
Layering is the name of the game when it comes to dressing for fluctuating forecasts and environments — add or remove one or two pieces and your outfit can feel and function entirely differently.
While wearing a T-shirt on its own or underneath a sports jacket might not be office-appropriate, removing your sweater once you get to the bar or restaurant afterwards (with the sports jacket on or off) is more than acceptable.
Depending on the dress code, casual pants can cause controversy at the workplace, though there are a few ways to circumvent that.
An inconspicuous pair of dark denim jeans appear far more formal than those washed in a lighter blue colour, which rules out any artificial fades and distressing.
If those feel too casual, look to their natural-born cousin: the 5-pocket pant. Made in largely the same construction but with a more refined fabric and finish, 5-pocket pants are a reliable mid-ground between jeans and chinos.
Sneakers have crept their way into modern work wardrobes over the past few years, though you can’t exactly get away with wearing any old chunky trainers. For them to be seen as office-friendly, they need to have a sleek silhouette, low-profile sole, and a refined upper — preferably leather or suede.
These will provide all-day, all-night comfort and will prevent your best dress shoes from getting dirty or damaged during your after-hours adventures. And after all, sneakers are more suited to the decidedly more casual environment anyway.
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