A few weeks back a reader asked me for help on creating shorts and footwear combinations for his outfits. Although this is something a lot of you might do without much thought, it can be tricky to get right; you need to be aware of how your outfit is proportioned and your footwear becomes even more obvious when you do not have a longer trouser hem to connect them with your outfit.

Although this article is not very timely, I am actually about to take a well earned summer holiday next week so I have been thinking about this myself a lot recently. I am hoping some of you will also be in the same position as myself and looking forward to a late summer holiday, or we as a nation still have some late sunshine left in this so called “summer” season.

Today I will be creating an almost pocket guide to the combinations you could create with your short and footwear styles, along with some look book images and current product selections.

So, without further ado…

1. Shorts & Sandals

Let’s start with the basics. Sandals are true summer footwear but a lot of males still shy away from using them within their outfits. Many will stick to flip flops, espadrilles or trainers, as they are easy to wear and a lot more widely accepted. Sandals have long been associated as being slightly feminine, or on the other end of the spectrum, with the unfashionable who (despite a plea from the world as a whole) continue to wear them with socks.

However, sandals are usually constructed of leather and come in styles that are very similar to shoes. With menswear as a whole moving towards a much more refined silhouette and overall sharper look, I cannot see why they haven’t seen their popularity rise. Infinitely more smart than your Havaianas, they lend themselves very well towards tailored shorts, polos, blazers and other smart casual items.

Shorts & Sandals Look Book

Shorts with Sandals Look Book

How To Wear & Tips

So let’s pick out some key points that are emphasised by the look book above:

  • Versatility: Sandals are very versatile and can be worn with everything from scoop tees and denim shorts [bottom center], to tailored shorts, shirts and blazer combinations [bottom right]. This versatility comes from the timeless nature and smart aesthetic leather produces. It will instantly bring a casual outfit up a notch, whilst it will never let down more formal pieces either – a lot like a classic pair of leather shoes would.
  • Choose Neutrals: Opt for a classic leather pair in a neutral colour such as white, black or brown, and they will coordinate with every single other colour you can think of. My personal choice would be brown, which looks just as good with blues and greys [bottom centre & right] as it does with summer colours like yellow [bottom left], and other earth tones such as khaki and green [top centre / bottom left].
  • They Are Timeless: Sandals are timeless pieces of footwear which will serve you well for years. They can be brought out each spring/summer season in order to sharpen up your holiday or casual outfits. You can either opt for a simple toe thong pair [top left] or for the more adventurous, try a gladiator sandal that will really add some edge and individuality to your look [top right]. Keep the detailing down to a minimum and opt for good quality leather [perfect examples top centre / bottom left]. These styles will transcend trends, whilst the leather will continue to look better and better with more use.
  • They Suit All Leg Types: Sandals are usually slim both in style and sole, meaning they are perfect for skinny, muscular or larger legs. For skinny legs, opt for thin strap styles which are a lot more subtle and won’t dominate your slender frame. For those with thick or muscular legs, you can get away with a much thicker strap. Just make sure they fit so they do not create unsightly bulges on your feet and/or ankles.
  • Advice For Short Legs: Shorter males will definitely benefit from a low sandal style which finishes around the ankle (or traditional thong flip flop style sandals) as this will give the appearance of a longer leg and create extra length between the bottom of your shorts hem and your footwear. Opting for a neutral brown, tan or nude colour is a trick a lot of women use as it gives the appearance of a longer leg – especially when you have a tan (blends in with skin tone). Finally, make sure your shorts stop above knee length to really emphasise the amount of leg on show. All these tips will help give the illusion of more leg length.
  • Advice For Long Legs: If you are a tall male who is conscious about your leg length and looking ‘lanky’ then don’t be afraid to opt for a gladiator style which finishes just above the ankle (similar to a short boot). This time, choosing this style will break up the long lines of the leg and shorten the gap between your shorts hem and footwear. Opting for a dark brown, black or even bold white colour can make your sandals stand out even more and break up your silhouette further. Shorts should finish around knee length, but make sure they are still have a tailored or slim fit.
  • Eton Shorts
  • Grey Twist Denim Short
  • Burberry Brit Cotton Cargo Shorts
  • Gingham Check Shorts
  • ASOS Chino Shorts
  • Marc Jacobs Leather Sandals
  • Albion Leather Sandal
  • Balenciaga Leather Sandals
  • KG By Kurt Geiger Breeze Gladiator Sandals
  • Duncan Leather Sandal
  • Paul Smith Shoes & Accessories Leather Cross-Strap Sandals
2. Shorts & Shoes

Another combination overlooked by a lot of men, shorts with shoes can look great if you get the styling and proportions right. Many men do not feel comfortable pairing shorts with shoes because shoes are very much a formal item which can look out of place when mixed with a more casual pair of shorts.

However, with the continuing rise of the casual shoe – namely bold coloured and suede versions – it has never been easier to integrate smart footwear into your shorts summer looks.

Shorts & Shoes Look Book

Men's Shorts & Shoes Look Book

How To Wear & Tips
  • Create a Look For YOU: The look book above should show that there is are many looks you can create with your current shoe collection. Whether you prefer loafers, deck shoes, a more formal style or brogues, you can build your outfit from the ground up and they will never look out of place.
  • Loafers: Loafers lend themselves very well to being styled with shorts as they usually have a low profile and give the appearance of slip-ons/espadrilles. They also benefit from the fact that even though they look smart, having no laces gives off a more relaxed aesthetic – meaning they can be mixed with everything from casual tees and shorts [bottom right] to more formal pieces such as tailored shorts, shirts and blazers [top right].
  • Deck Shoes: Deck shoes are perfect for pairing with shorts, and are often used as such within the Nautical trend. However, I prefer to not be so obvious and that is why I like the fact that in the look book above we have a true Nautical outfit paired with loafers [bottom right], whilst we have gone with a completely different look when actually utilising the deck shoes [top centre]. What makes the deck shoe outfit so good is the fact that they have hinted at the Nautical trend via deck shoes and navy tailored shorts but transformed the focus using a statement t-shirt which hits the colour blocking trend instead. Utilising common pieces in new ways (and with unexpected trends) is great way to produce an individual style which will set you apart.
  • Consider Material: Obviously in spring/summer you need to be aware of the material you are choosing for your shoes. It can be sweltering wearing a leather shoe, but what is more important is the aesthetic each material can give off. Suede shoes are much better suited to casual outfits [top centre / bottom left], whilst true leather shoes can give a much more refined and even formal appearance [top left]. For those of you looking for somewhere in between, a distressed leather pair can be used with smarter trousers and chinos, just as well as it can be worn with tailored or casual short styles [bottom centre & right].
  • Colours: In the summer you should be dressing for the season, and this usually means lighter materials and also lighter (or bolder) colours. Try to stay away from black shoes when pairing with shorts as they look stuffy and too formal for the look we are going for – usually casual or smart casual. Brown work very well as a balance between smart and casual, with tan being my personal preference. Other light neutrals such as grey [bottom left] and beige [top centre] look great and allow you to dress up or dress down dependant on your mood.
  • Skinny Legs: For those with slim or skinny legs, you should opt for a shoe style which has a low profile, thin sole and a slim (not clunky or chunky) overall appearance. You do not want the shoes to dominate your legs and look out of proportion – this is the number one thing that can kill an outfit when wearing shorts. Even the traditionally thicker styles such as deck shoes and brogues now come in slimmer silhouettes these days, so you will still be spoilt for choice.
  • For Short Legs: For men with short legs, you can opt for a thicker style sole or small heel (most shoe styles have this) which can give you a boost in height without looking like you are ‘trying’. Something like these COMME des GARÇONS SHIRT Brogue Shoes are what I mean by a thicker sole. Remember though that you also have to take into account your leg type; if you have skinny legs you will not get away with chunky shoes and thick soles as they will overpower your slender frame.
  • For Thick or Muscular Legs: If you are carrying a bit of weight or have thick/muscular legs, you have more options available to you. You can opt for slim styles which will not draw attention to your footwear and allow the rest of your outfit to shine, or go the other way and use thick or chunky styles which can become a real focal point. The reason you can opt for thicker styles is because they will be much more in proportion to the thickness of your legs, giving balance to your top and bottom halves.
  • Stone Cotton Twill Short
  • Kenneth Cole Relaxed casual short
  • ASOS Chino Shorts
  • Mustard Chino Short
  • Burgundy Cotton Twill Shorts
  • ASOS Roll Up Denim Shorts
  • H By Hudson Cairo Woven Slip-On Shoes
  • SPERRY Authentic Original Olive Canvas Boat Shoe
  • Maintain Shoe
  • HUGO By Hugo Boss Prayor Suede Derby Shoes
  • MARK MCNAIRY<br /> Loden Green Suede Derby Shoes
3. Shorts & Boots

Shorts paired with boots has been a trend a lot of designers have tried to push over the last two consecutive spring/summer seasons. Here at FashionBeans they have had mixed reviews from both readers and the staff. Boots and shorts may seem mutually exclusive to the average male but with the amount of styles, choice and options we have within men’s boot these days, it means we can definitely find a way to pull it off successfully.

Shorts & Boots Look Book

Men's Shorts & Boots Look Book

How To Wear & Tips
  • Military Boots ARE Versatile: Say what you like about the Military boot style, but the look book above does prove its versatility. No we don’t all have to wear them with deep scoop tees ala JLS; they can be utilised in Nautical [bottom right], Safari [bottom centre], Rocker [top left] and even American Vintage Double Denim [top right] trend inspired looks just by altering your surrounding pieces. If you already have a cropped Military pair of boots, why not try mixing them into one of your outfits for those cooler spring/summer days, or even in the transition to autumn?
  • Consider The Weather: It may seem like common sense, but boots – especially leather – are going to be much hotter to wear than trainers, sandals or shoes. It is just a fact due to their construction and nature. So, these are not going to be looks you can pull out on a hot summers day without feeling uncomfortable. Instead, these could look great when the temperature drops at night, cooler spring days when mixed with a lightweight trench [bottom left / top left] or when you are creating layered looks in early autumn [top right].
  • Socks Are a Great Accessory: When mixing boots into any outfit, you should consider the benefit of a long chunky sock. They can either add intrigue through patterns [bottom right] and colours, or simply give your outfit another layer whilst simultaneously break your leg line up further [top left]. They work particularly well with outdoorsy type boots when trying to hit Nomad, Town & Country or worker wear trends – all very prominent in the early autumn.
  • Short Boot Styles Work Well: An easy way to get in on this trend is through shorter ankle boot styles, which do not overpower your frame and are going to be much more comfortable to wear on warmer days [top centre]. Styles such as chukka, desert, deck or short brogue boots are particularly prominent right now and come in every style, material and colour you could possibly want. These would be easy to sub in for those of you who already wear hi-top trainers, Converse or traditional shoes with your shorts.
  • Hiking Boots: This boot style became very popular last autumn/winter and it is one of my favourite types of footwear right now. With the new season I think we are going to see the rise in popularity in this type of boot, especially in those males looking to move away from the Military styles and the stigma attached to them. They look great when paired with smart casual pieces [bottom left], as the clashing of city inspired clothing with boots that have roots in the countryside gives your outfit that perfect ying yang balance. This new style would also work very well with other outdoors and heritage trends such as tweed blazers and earth tones, whilst I can also imagine them looking amazing within the Safari/Hunter inspired clothing we are going to see this autumn/winter [bottom centre].
  • Skinny Legs: For those with skinny or slim legs, you can still wear boots but make sure they are done up and follow the line of your leg closely [top centre]. This will help create a sweeping line down the leg and will not have you looking like you stuck a broom handle in a bucket. The other option would be to opt for a slightly thicker style but utilise socks to ease the transition from the footwear to the leg line [bottom right].
  • Muscular/Thick Legs: For those with a larger frame or thick and muscular legs, you can pretty much get away with any style of boot. Your body will be in proportion whether you pick a chunky military style or slimmer desert type style. You can also get away with leaving the boots loosely undone to create a more relaxed or fashion forward aesthetic.
  • Short Legs: For those with shorter legs, my advice would be to opt for a shorter style – whether that be a short cropped military boot, desert or chukka. The reason behind this is that you don’t want to shorten the length between your shorts hem and footwear so much that it makes your legs appear even shorter. The other key point to note would be that by doing up the boots you create a long sweeping line down your leg that is not broken up so obviously by the top of the boot – again it just gives the illusion of more length.
  • Long Legs: For those of you with long legs, boots can be a great way of breaking up the length and reducing the amount of leg on show. Tall styles such as Military and the new hiking type boots are great for this and become a real focal point to your outfit. Another great way of shortening the length even further would be to utilise a sock which can peek out the top of your boot to break up then leg line and add another element to your bottom half.
  • JAMES PERSE Vintage Fleece Sweat Shorts
  • Khaki Needle Cord Shorts
  • J.Crew Stanton Cotton Shorts
  • Humor JA Denim Shorts
  • ASOS Chino Shorts
  • Black Chino Shorts
  • H By Hudson Westland Military Boots
  • Alpine Boot
  • Point Boot
  • Swear Oxblood Leather Duke Hiking Hightops
4. Shorts & Trainers

Of course, every single male reading this article will probably of paired some trainers with shorts before. It is so easy to do and you can create a plethora of looks quickly and easily if you have a simple pair of Converse or leather trainers on. With the amount of styles, colours and cuts available within the menswear market these days, it really just comes down to personal preference and choice.

With that in mind, I have sourced a few images showing you just how much versatility there is when utilising shorts with trainers, and I will just give some basic tips below for you to consider.

Shorts & Trainers Look Book

Men's Shorts & Trainers Look Book

How To Wear & Tips

As mentioned above, you can create so many different looks with a pair of trainers that it would take forever to explain them all. Trainers are personal preference and can be as casual or formal as you prefer. They go with board shorts, camo shorts and lounge shorts [bottom centre & right / top centre] just as well as Preppy inspired looks and even more formal bow ties [bottom left / top left].

Key Points:

  • By keeping your trainers refined and stripped back, you CAN create some amazing smart looks which look much more relaxed than when matched with shoes [bottom left / top left]. White leather trainers are a wardrobe staple which you can pair with cricket jumpers, shirts, blazers, ties and polo shirts effortlessly.
  • Utilising neutral coloured trainers (such as black or white) means you can experiment with the rest of your outfit. You can add interesting colours and prints [top centre / bottom centre], patterns [bottom left / top left] and colours, safe in the knowledge that your shoes will anchor the whole look.
  • Hi-tops are very much like boots and the same advice would apply. Tall hi-tops help break up long legs and can be paired with thick socks [bottom right]; thick/chunky styles will suit thick or muscular legs; thin and done up hi-tops (such as Converse) are great for those men wanting a hi-top style but are wary of creating a shorter looking leg or naturally have thin legs.
  • Polo Ralph Lauren Checked Short
  • Carhartt Floral Print Board Shorts
  • Uniforms For The Dedicated Stone Black Shorts
  • Polo Ralph Lauren Fielding Tailored Cotton Shorts
  • french connection Mens Cuckoo Vintage Wash Shorts
  • Irreverence Chuck Denim Shorts
  • Keds Plimsolls
  • adidas originals Mens Summer Deck Off White Canvas Trainers
  • Mix Brandon Hi Top
  • ASOS Retro Sports Plimsolls
  • Mens Vans 106 Vulc Trainers
  • Mens Converse All Star Clean Trainers