How To Wear Shorts

How to wear shorts

The Fit | The Length | Patterns | What's in Style | Body Types | What to Wear With Shorts

A shorts guide

A brief guide to wearing shorts - what to look for, how to choose the right pair to match your build, and how to style them. Even though there are no hard and fast rules when it comes to putting on a pair of shorts, it's useful to keep a few things in mind. And once you master the art of wearing shorts, you can break the rules in style.

How are Men’s Shorts Supposed to Fit?

A well-cut and properly fitting pair of shorts is not just more comfortable - it will make you look better. A tailored pair of shorts will define shape and create a flattering profile regardless of your size or build. They should feel comfortable and fit your body shape, without being too tight or restricting movement. And don't be afraid to show off a little leg! Be confident. It might take a little getting used to the first time you put on a tailored pair of shorts, but your legs will thank you for it.

There are shorts available to suit every body type; you just need to find the right pair for you. For most body types, it is advisable to avoid baggier styles in favour of a more fitted pair; loose styles generally tend to make legs appear smaller, whilst at the same time making your upper body seem bulky. Not quite the look you're after.

Unlike pants, which generally tend to follow your legs all the way down and are defined by their shape, shorts can quickly become shapeless and unflattering if they're ill-fitting in any way. The longer and baggier you go, the more fabric will be flapping around, and you'll risk losing shape and definition.

In contrast, a properly tailored pair of shorts that's suited to your body will balance out your shape, by giving definition to your legs and working with your waistline, adding bulk where there is none and trimming down where there is plenty.

Navy Huck 5 Tailored swim shorts

To make sure you're on the right track, here are a few things to consider when you come to pick your next pair:

  1. Opt for a sleek flat front: baggy shorts don’t complement any body type and won’t hide anything;

  2. Beware of elastic waist bands as they tend to emphasise the keg belly and love handles;

  3. Choose shorts that don't flare at the bottom: narrow leg openings help to define shape;

  4. Keep the length well above the knee for an on-trend tailored look.

Ultimately, men’s shorts are supposed to fit in a way that makes you look great, feel comfortable, and move with ease. You don't need a great body to look great; you just need your clothes to fit.

What Length Should Men’s Shorts Be?

Wearing shorts is about confidence and finding the right length for your shape. Knowing where your shorts should fall is something you learn with experience. You may have always opted for a shorter short but this might not suit your body shape, or you've been tempted to hide your legs with longer shorts that might not have had the desired effect. As a basic guideline, here are the most suitable shorts styles based on your height.

Very tall men should opt for mid-length shorts; longer styles will only draw more attention to your height, whilst shorter shorts on thinner legs can have the beanstalk effect. It’s all about confidence and how you feel about those legs though - if your quads deserve the spotlight, go ahead and show them off.

Men of a more average to medium height are fortunate in that they can look good in any length; just don't go below the knee.

If you’re a shorter man, be bold: you have free reign to go even shorter in length, as the long and baggy styles will swamp your style.

Huck 5 Camo Marine Designer Swim Short

Choosing the right colour

Everyone has their favourite colours and patterns, and having the guts to go with what you love is great. But there is also real benefit in understanding colour theory and opting for styles which generally suit your style and complexion. Certain colours look better with pale skin whilst others are ideal for darker tones, and patterns are a different ball game altogether.


With a paler skin, you'll look best in darker colours which contrast with your skin tone – bottle greens, deep slate greys and brown, as well as navy and vibrant blues work well. Black and white combinations are a no-go, as well as too many pastels or bold brights, as they will simply wash out your skin tone.

As the skin tone darkens, you can work more pastels and brights into the mix, and the same goes for neutrals such as sand, camel and khaki hues.

For olive skin tones, go bold. While most colours will work well with a medium skin tone, you'll get the best results in shades that are either a little brighter or darker than the middle ground; choose a deep orange or a royal blue instead of their faded variants. Avoid colours and shades that blend in with your skin tone.

Guys with darker skin tones, take your pick. You can go for whatever colour takes your fancy, as long as they contrast with your skin; be brave and try your luck with bolder options, including prints and patterns. Darker colours like black and navy still work, but try to limit them in your outfit and incorporate a complementary colour to make it work.


Combining patterns with patterns is an art in itself, and you almost have to approach pairing patterns with the intent of not matching. A useful rule of thumb is to at least make sure your patterns are different in scale; for instance pair your large check suit with a thin stripe shirt and a micro-dot tie. Other than that, there are no rules to pattern matching; it takes experimentation and practice.

For most, patterned shorts are best paired with neutral or plain tops to avoid getting too busy. If you're unsure about pattern matching but you still want to make a statement, in most cases you’re better off pairing your patterned shorts with a bold plain coloured shirt rather than risk clashing prints.

A pattern will always draw attention to the body part you’re wearing it on. For example, if you want to show off your legs but don’t feel comfortable with your upper half, wear patterned shorts with a neutral top for a look that isn’t too loud. Any attention will go to the shorts, ultimately complementing the section of the body you don’t feel comfortable with.

Five Mistakes Made with Shorts

1. Socks

Can you wear socks with shorts? Admittedly, the shorts-socks combination can go horribly wrong. However there are exceptions where it works exceptionally well, like retro ankle length sports socks for a street style vibe, or heavy socks in outdoor boots for a rugged look. Most shoes that look good with shorts can be worn sock-less though, and if foot odour or sweat is an issue, ankle socks are your best friend.

Huck 5 stone tailored shorts and shoes

When in doubt, leave the socks in the drawer; going sock-less with shorts is a great summer look.

S001 black linen shorts

Keep your shorts above the knee for a contemporary, confident look.

2. Below the Knee

There's no need for shorts to fall below the knee. Whatever style shorts you prefer, you'll want to keep them above the knees to keep your legs cool and to make it easy to move around. Longer shorts pretty much defeat the purpose of wearing shorts altogether; they're less comfortable, won't keep you cool and you're at risk of looking like a schoolboy in hand-me-down Bermudas.

3. Skin Tight

There’s a fine line between well-tailored shorts and showing off a little more than you should. Unless you're engaged in an extreme sport or running for your life, skin tight styles are never a good look and they are almost guaranteed to make you feel uncomfortable, and likely self-conscious too. Choose tailored over tight and avoid the moose knuckle.

S001 white linen shorts

Leave a little to the imagination when wearing shorts; tailored but not tight.

Close up of Huck 5 Undertow Charcoal shorts waistband

Choose a fixed waistband to avoid getting squeezed in all the wrong places.

4. Muffin Top

Slim fit shorts are one thing, but if you have to squeeze yourself into them, chances are you're going to squeeze something out, and usually it's the waist. Even with your top on, those love handles will be there for all to see and you can avoid it simply by picking shorts that fit. Elasticated waists are the main culprit for forcing that unfortunate muffin-top look, but it can also happen if you’re trying to fit into shorts that are simply too small.

5. Too Short

Even though men's shorts are getting shorter, with most shorts now comfortably above the knee, there is such a thing as too short; the words "hot pants" shouldn't be used when describing you. Getting the length of your shorts right is about personal judgement but if your whole thighs are on show, even if they’re perfectly toned, you’re probably going a little too short. Anywhere between two and four inches above the knee is the perfect length for a tailored pair of shorts.

Huck 7 whalebone red preferred length tailored shorts

Find the right length for your body type and legs.

Choosing Shorts to Suit your Shape

Male body types

Your body shape plays a key role in getting the perfect pair of shorts, and there are shorts to suit all shapes. Here we’ve broken down the four main body types in some detail, followed by recommendations for how to pick the ideal shorts for each shape.

1. Average to Athletic

Broad shoulders and a taper downwards towards the leg (the trapezoid or inverted triangle body shape) is often considered the most sought after body shape. With an athletic build, you have free reign when it comes to picking shorts but always remember to keep your height in mind when choosing the length and style.

When dressing according to body style, it is all about balance; with broad shoulders and biceps, you’ll want to avoid shoulder padding for risk of appearing top-heavy, and for the same reason don’t go too skinny on the pants. A slim fit tailored style can show off this body shape nicely; again, don’t go too slim when it comes to the shorts (avoid skinny) and try keeping them light-coloured to offset the upper body bulk. You’re also quite flexible when it comes to choosing patterns and prints, as appearing widened (horizontal stripes) or stretched (vertical stripes) is not much of an issue. Just steer clear of overly bold prints on the top half.

2. Tall & Slim

Tall and thin with a shoulder width that approximately matches your hips is referred to as the rectangle. This body shape is quite common and it can be hard not to fall into boring fashion choices, living in t-shirts and jeans. The goal here is to rebalance the shape by adding width to the shoulders while keeping the bottom narrow.

Rectangular bodies suit slim fit jeans and shorts, as this will create an inverted triangle or trapezoid line (make your shoulders appear wider and your waist narrower) that will give more definition to your shape, and shorter shorts often go down well too. Bold prints and patterns can also make a straight-up-and-down body more interesting; you can opt for printed tops or printed shorts, or a subtle mix of both.

3. Short & Stout

The oval shape is something that many men find themselves growing into, whether athletic in their youth or not, and some younger men are just naturally rounded. Your body has a roundness to it, with a large chest and tummy, but both your shoulders and legs are quite slim in comparison.

Shorts for this body type should be more fitted and slimline, to show off those legs. Wearing baggy styles on slimmer legs will drown them out and give them the appearance of being much scrawnier than they are. Try to avoid contrasting colours between top and bottom as it will emphasise the oval shape, and instead choose darker colours for both. Go for shorter shorts, and wear them at your natural waistline, closer to your belly button; don't wear them too low as this will make your legs look shorter. Experiment with lighter fabrics that add less bulk, like linen.

4. Soft in the Middle

For the triangular-shaped body, where your hips are wider than your shoulders and you have a bigger waist, it’s a good idea to avoid those slimmer fits. At the same time, resist the temptation to hide under a huge suit; tailored shorts still look stylish when bought in the right size and opting for flat-fronted designs allow your waist to be skimmed over.

Go for straight leg shorts, as tapered legs will add more width to your waist. Crew neck tops teamed with tailored shorts look particularly stylish on the triangular shaped body and it is often a good idea to stick to more classic patterns and colourways, rather than going for anything too busy as this will simply draw attention to that particular area of your body. Try darker colours like charcoal, navy and black to help hide your size.

What to Wear with Shorts

How to wear shorts

There are many occasions where shorts are the perfect solution. A good pair of shorts can be dressed up and down to be worn casually, for smart outdoor occasions, and even for special occasions such as a beach wedding.

Key pieces which look great with shorts:

A great way to combine printed shorts is with a fitted plain t-shirt; throw on a white or black plain tee and you pretty much cannot go wrong. For a more formal look a polo could be worn or a shirt, as long as the shirt is tailored and not too long, or combined with a belt if tucked in, to keep the balance between top and bottom.

If it gets chilly, try layering by throwing on a long-sleeve tee, henley shirt or jumper. Make sure it’s not too bulky in fit and fabric as it might throw off the balance between top and shorts.

The shorts suit has recently gained in popularity; it’s a great look if one that can easily go wrong, so keep in mind a few pointers. Make sure your shorts aren't too short, and keep the shirt & jacket tailored so they don’t cover the shorts too much. Ideally your jacket would match the shorts in style and fit. A great style for outdoor occasions.

There are many great alternatives to flip flops when it comes to footwear to wear with shorts. Make sure the shoe matches the style of the shorts; pair casual with casual and smart with smart. On the casual side espadrilles, canvas trainers and plimsolls are good options, or white sneakers with ankle socks (or ankle length sports socks for more of a streetwear vibe). And for a more formal look try loafers, huaraches, or leather sneakers, all of these without (visible) socks to keep the casual feel. Hitting the outback? Combine desert boots with stone or khaki shorts for a rugged, outdoors look.

How To Measure For Men's Shorts

One of the main things to get right when choosing a pair of shorts is the size; and the more formal you go, the more it matters. Fear not, because there are easy ways to measure for a pair of shorts. Obviously the best results would come from a visit to your tailor, but if that's not an option then there are ways to do this at home. You'll need a tape measure.

There are four main areas to check when measuring up for a well-fitting pair of shorts: waist, hips, inseam and outseam. Of these four, the waist and outseam are the main ones you'll need when buying a pair of shorts, as these are the most commonly referenced measurements in retail. All measurements should be made to the nearest centimetre or quarter inch. 

Waist measurement

WAIST: this refers to the size you'll be choosing

  1. Fit the measuring tape around your waist: locate your hip bones and wrap your tape measure around your abdomen above the top of the hip bones, making sure the tape sits flat.
  2. Adjust the tightness to what feels comfortable, but make sure there is at least enough room for an index finger inside the tape.

Outseam measurement

OUTSEAM: the length of the shorts

  1. Place the measuring tape at the waist (where you'd like the shorts to sit) and measure down the leg.
  2. Take the measurement where you'd like your shorts to end.

Hip measurement


  1. Measure around the fullest part of your hips/buttocks and round to the front.
  2. Make sure both ends of the tape meet and that the tape is straight. You should just slightly feel the tape, without pulling it too tight.

Inseam measurement

INSEAM: you'll need some help with this one

  1. Measure from the top of your inside leg, at the crotch, to where you’d like the shorts to finish (matching the outseam measurement taken previously).

So there it is; a starting point on how to wear shorts, aimed at making you and your legs look your best when the mercury rises. Keep these guidelines in mind and you’re all set to score some style points on the beach this summer.

Not quite sure? Get in touch for advice on which shorts are right for you.