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Ask Harry: How to Wear 1 Sports Jacket 3 Ways

Our How-To Guide on Styling the Same Sports Jacket with Three Different Outfits.

By: Harry Rosen StaffDate: 2023-05-16

It's been said before that a sports jacket is among the most versatile wardrobe essentials a man can own, though putting that into practice is something some men still struggle with; at least, those who aren’t accustomed to wearing tailoring.

Here, we’re running through a few different ways you can sport a jacket from formal through casual, exemplifying just how easy it can be to look great in a tailored jacket. Here’s how to wear one sports jacket three different ways.

The Suit Separates


Sure, a full suit is the easiest way to achieve a traditional business look, but breaking one up with a contrasting sports jacket and trouser pairing means you can shake things up without sacrificing much in the way of formality.

The quintessential separates combination is navy and grey — two of the most common suit colours — though don’t feel your palette is limited. A good rule of thumb is to opt for one lighter colour and one darker colour as separates that look too similar can make your look appear washed out and unintentional. That said, if you know how to pull off a monochromatic outfit, all the power to you.

The Smart Casual

Taking things down a touch in formality, this second sports jacket-based look balances the line between dressed-up and dressed-down.

Swap out your shirt and tie for a piece of fine gauge knitwear, which will retain some sense of dressiness while making the entire look feel more at-easy. The same goes for your suit trousers — swap them out with a pair of more casual chino pants. Anything from loafers to slip-ons to a smart sneaker will do on-feet here.

You don’t need to be heading into the office to wear this type of look, but you very well could if you wanted to.

The Elevated Casual

Even your off-duty casual outfits can benefit from wearing a laid-back sports jacket over top. Jeans and a T-shirt are great on their own, but adding a softly tailored (or even better, unlined) sports jacket to the mix results in a winning equation.

Wear this to a cool new hotel bar, try it out on a dinner date, or even just to take the dog for a walk; the opportunities to are seemingly endless. 

Have a sartorial problem on your mind? Send us a message on Instagram @harryroseninc, and we’ll answer it here next time.
TAGS:#Style Advice,#Trends,#Sport Shirts,