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Style Advice

Style SOS: Which jacket should I invest in for every day?

Style SOS: Which jacket should I invest in for every day?

I’ve been wearing the same black jacket for the past few years and I’m due for an upgrade that feels classic and versatile. Which kinds of styles should I be looking at? - George via email 


Kudos for keeping your jacket for so many years, and if it’s still in decent condition, there’s no reason you have to retire it forever. But we understand your desire to add a new go-to to your jacket rotation, especially as we enter a new season.

Something we’ll caution you not to do is purchase one that looks eerily similar to your existing piece. It’s a lazy shopping habit we’re all guilty of making: finding a style we like that’s flattering and versatile, then buying three or four more pieces that look just like it. Owning a variety of pieces enables you to easily switch up your look, experiment with your personal style, and step out of your comfort zone. So challenge number one when scouting out your new jacket is to change up the silhouette and colour. You mentioned your current jacket is black, which is one of those goes-with-everything shades, but we’d argue there are others that are equally versatile and more visually interesting. Jackets in neutrals – think tans, olives, and navys – are a great place to start. They complement most other colours and are always in style.

In terms of versatile silhouettes, there are a few tried-and-true styles we’d recommend. Thread stylist Alexander McCalla suggests the classic Harrington jacket, a style sported by many style icons, from James Dean to Elvis. “They look sharp on guys of all ages and they have that timeless quality to them,” he says. This navy take by Baracuta will add subtle colour to your everyday look.

Alexander also notes that you can’t go wrong with a great workwear jacket, like this chore jacket from Carhartt or a denim trucker from the OG, Levi’s. They’re workhorses in any wardrobe and tend to look better with wear, so will only improve when you reach for it the 20th, 30th, and even 100th time. But if we had to pick a top contender for your new go-to jacket, it would have to be a trench coat, like this minimalist style by A.P.C. It’s as classic as jackets get and it comes through strong in inclement weather. It also gives you that air of mystery that prompts people to wonder, “What’s his story?” and “Where is he going?”. But never, “When is he getting a new jacket?”.

Words: Allison Pavlick
Illustration: Ryan Gillett