How To Style Shorts This Summer

Written by Bronwen | 01/07/2020

We understand, the sun is finally out, it’s hot and you want to wear shorts; but every time you do you feel like an awkward 12-year-old and quickly switch back to trousers. Just because it’s casual wear doesn’t mean it’s easy to match, so here are Mainline Menswear top tips for wearing shorts in summer.

When NOT to wear shorts

When are shorts not appropriate? Sometimes it just isn’t appropriate to get those legs out. Examples include: weddings, the office and funerals (seriously, don’t), a basic rule of thumb is to ditch the shorts if you’re expected to wear a blazer in the situation. Parties, BBQs and the beach are all great places to give those legs a bit of fresh air.


The Fit

It may seem simple, but the length of your shorts can change (and ruin) the whole look. Shorts are meant to be comfortable, and a perfect fit depends entirely on your body shape. Short shorts will make a man look taller (and like he’s just stepped out of the 80s, but that’s another issue), while long shorts will make you look shorter, but go too long and you’re just wearing cut off trousers – which is an entirely different style and, quite frankly, should be avoided at all costs.

To make things easier we’ve broken the basic rules down for you. Don’t say we never treat you:

1) The length: If you’re tall, don’t just go for the longest pair of shorts available because you’re built like a basketball player – unless you’re going to play basketball I suppose.

Tall or short, long shorts will look scruffy and widen your legs. No matter your height, try to find shorts that sit comfortably 2-3 inches above the knees. If you’re struggling for that perfect pair, you can always roll long shorts up a few inches and see how that looks.

2) The width: A common mistake from both men and women is to buy baggier clothes because they think it will make them look slimmer. This is not the case! And if you have a bit of meat on your bones you’re better going for your regular size when it comes to shorts. Everything needs to fit correctly, so don’t go for really baggy.

Boss Casual


If you’re feeling a bit nervous about those bare legs being on show, then we recommend you keep things simple for now. Clean, block-coloured shorts will mean you can rest assured that you look fine, and they will be easy to match. An easy outfit that Mainline Menswear recommend is a pair of Chino shorts (smarter than denim), matched with a plain t-shirt. This outfit is simple and easy to pull off.

A man looking back at the camera wearing Lacoste shorts


Feeling bolder?

So you’re past the simple shorts phase? You’re feeling bolder, stronger, faster! And ready to show off those knees with pride. If this is the case, then make sure things match. If you’re wearing brightly patterned shorts then you can’t wear a brightly patterned t-shirt as well, you need to make the rest of your outfit simple with a plain shirt.

Likewise, if you go for strong colours such as burgundy, green or yellow, then your shirt needs to be a simple colour to match, like grey or white. Basically, the general rule is that bold shorts = neutral t-shirt and shoes. Follow these rules and you’ll be looking and feeling confident in your statement shorts.

Man lying next to a pool wearing Fila Vintage yellow shorts

Shoes That Go with Shorts

Finally, we have your footwear. Different shoes apply to different situations. For a more casual outfit, and to match with your plain shorts on a sunny day, then you can’t go wrong with sandals. Mainline Menswear recommend our range of Birkenstock sandals, made with real leather and easy to match, you won’t have to worry about matching your outfit with your shoes.

If you’re going for white shorts, however, then sandals simply won’t cut the mustard. We recommend you wear boat shoes or loafers instead. It’s a classic look that turns an otherwise casual outfit into something much smarter. Complete your French Riviera outfit with a short-sleeved shirt rather than a t-shirt.


Some brown GH Bass Shoes

Final Thoughts

There we have it, five simple rules for pulling off shorts. Though only suitable as casual wear, a lot can still go wrong with a good pair of shorts, so follow these steps and you’ll be looking and feeling cool this summer.

Our main piece of advice would be to not worry too much about what you look like; unless you end up with the Magnum PI look – in which case find some shorts that get a little bit closer to your knees – unless your names Tom Selleck.


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