How to Wear Long Shirts

by Jamie Wilson

Reviewed & updated: October 19, 2022 by Jamie Wilson BA

Long shirts are a trend that we can’t see going away anytime soon, and this style guide will show you how to pull it off this season.

The long line trend has grown in popularity in a pretty big way over the past couple of years, and long shirts are now a part of that. They can be quite a daunting prospect to style but it’s not difficult to get a interesting and unique look that’s great for when you want a more complex look.

It’s a style we probably wouldn’t suggest for shorter men, as it won’t be the most flattering piece for your height, however, it can be an ideal wardrobe addition for the taller men among you. So let’s get to it and see how you can style this hugely individual piece.

90’s Grunge

The first look we’d go for is that classic 90’s grunge. The 90s are now a nostalgic time for many (we’ll let you decide if that’s a good thing or not) and with brands like Umbro, Ellesse and Calvin Klein all making a strong return, it’s about time we explored other styles from that pretty divisive era. With that in mind, the grunge look is a pretty good place to start. There’s a range of longline shirts out there, and you can either go for a simple black piece, or try a more eye-catching checked design.

In order to make sure your longline shirt doesn’t appear to be just be too big for you, make sure the sleeves don’t go further than your wrist and the overall shape is slim fitted.

One look is to go for checked shirt rolling up the sleeves and unbuttoning it to the bottom of the neck before pairing it with some relaxed fitting, stone washed jeans. Team this with a pair of Vans and you’ve nailed this classic look.


You could also try out a more conventional grunge look, incorporating the classic graphic tee and overlaying your shirt to give a dimensional style. Pair this with some ripped skinnies and slip on a pair of Converses to complete the (now vintage) 90’s style.

Classic Biker

A classic piece you can pair with a more contemporary longline shirt is the iconic biker jacket. Going for a waist-length jacket that’s less fitted, and matching it with a long, fitted shirt will give your outfit an interesting contrast and a unique boost.

For the jeans go for a skinny and black pair, button up the shirt and throw on a pair of lace up boots to go for a rugged yet refined look. This will give you a fairly traditional biker look, where the colours are muted, but the differing textures provide enough contrast to keep the outfit interesting. Mixing classic with contemporary can be tricky but this should be a pairing that goes really well together.


You can also try experimenting with some colour and a less refined finish, opting for light grey jeans rather than black, and choosing a pair of chunky Doc Martens over the slicker lace up boots. This will give you a look that still differs from the traditional biker look due to it’s contrast in textures and lengths, but that still has a distinctive edge.

how to wear a long shirt biker look

Almost Formal

It might sound odd, but there’s no reason that you can’t add a formal twist to a longline look. Playing around with different lengths is a striking yet put together way of creating a distinctive look. Try a pair of cropped chinos with your longline shirt, then add some extra dimension with a waist length blazer.

Finish off with a pair of leather loafers to keep the look centred in formality. This combination of lengths will keep the look jagged and complex, and is great for those of you who don’t want to advertise your height, as this plays around with the whole look of sizes.

how to wear long shirts smart

Layer Up

When the temperature drops and the need for layers increases, you should be looking at how you can incorporate your long shirt into your winter wardrobe. You can of course do this by simply adding a T-shirt under your shirt, but for a more noticeable look you can try layering a crew neck jumper over your shirt. Button up the shirt and pop the collar out, and keep the shirt hanging below the jumper.

This won’t look as strange as it sounds, and will simply add a little dimension to your outfit, especially when you add your coat over the top. Chuck on any jeans you feel fit, although we’d recommend something skinny or slim fit to emphasise the loose look of the top half, and add a pair of smart boots to complete the look. You can also try some slim fit chinos if jeans aren’t for you, which is ideal if you’re wanting to go for a smart edge.

You can experiment with colour here, and below we’ve chosen a light, preppy look that’s perfect for autumn, but you can do for a darker look with navy and black if you want a more alternative vibe.


End Note

Wearing a long shirt doesn’t have to be as restrictive as you think when it comes to style, and you can go for a few unique looks, even trying out a formal twist if you fancy it. Remember to keep your shirt slim line, long enough in the arm, and only wear it if you’re confident enough in your height. If you pull off this unique design you can create a range of contemporary outfits that can merge effortlessly with more traditional looks, and will help you stand out in the crowd even in a more simple outfit.

Feature image from Pinterest

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