The Best Shoes For Your Outfit

The Best Shoes For Your Outfit


Jeans are the easy standby for most men of this time. They are the ultimate trouser that can take a man from work through to the weekend whilst being so pervasive that they have become something of an urban background. For these reasons you would assume that they would go with any shoe; however you´d be wrong. Smarter styles of jeans are available, but there are unfortunately no brands or styles out there that are so ceremonious that they will look good paired with very formal or office style shoes. (I quickly insert here that brogues are the bad boy exception to this rule as they really do look good with everything). It is perhaps safer to leave the black lace up shoe and denim look for the indie bands or your colleagues on a works night out. Chelsea boots and brogues are typically as proficient as you can pull them off for most formalities but even then, they can cause problems for the jean / boot interaction unless they are both slim fitting and jet black – which most denim isn´t. (The most popular colour is actually stonewash blue – something that the classic, borderline cult Levi jeans have to be thanked for).

If your denims are the kind of stacked, distressed versions that rap-starts may favour, then they should always be paired with trainers – preferably of a minimal design (or more shall we say statement, if the denims are tamer). Style options which have the straighter, heavy selvedge type span back to tough men who did tough work in tough denim and for this reason you won´t go far wrong with thicker soled or sand boots to complete the look.




When it comes to conforming to the style of the good old Ivy League – preppy trousers always merit a preppy shoe. If it was good enough for American Presidents, then it´s good enough for you. As anyone worth their salt from the Hamptons will tell you, it’s; ¨deck shoes in summer, duck boots in winter and, all year round, loafers, worn with or without socks as the weather dictates.¨ If that’s all a bit too Ralph Lauren for you, then brogues add a certain antiquity couple to your look. The stylists trick is to let the gauge of your cotton dictate the thickness of your shoe.

Autumnal and winter fabrics deserves a hardier shoe. Utilitarianism is still prevalent in many fashion houses and hiking boots are still in trend, even for the kind of urbanite who defines an ‘excursion’ as being more than ten minutes from a Pret a Manger. Keep you look classy by avoiding multiple eyelets and garish nylon uppers and instead base your look on the type of polished leather that actual climbers haven’t worn for decades, while you discreetly show them off them off by hunching your chinos slightly up above the line of thick, woollen winter socks.


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Fashion is so often illogical that when a trend like jogging pants comes on the scene (that are the perfect marriage of affordability, versatility and comfort) you won’t have to spend a lot of time deciding what to wear every morning. Sports-luxe and athleisure by their sheer nature will be the perfect partner for statement trainers, plus they will allow you to indulge your more extravagant tastes safe in the knowledge that you netural, slim fitting joggers compliment the look perfectly. By the sheer aesthetic of this trend, dressing the look up (even when applying the fundamentals of sport-luxe and street trends) can be difficult. Dress shoes and joggers are never ever a good look, so the recommendation is that anything past Chukka boots is overkill. If you want some discreet visual interest from these, you can add some suede and since this shoe has its origins in the polo field, they will still retain a discreet element of sport – with just a little bit more luxe to your look.




Shorts are intrinsically casual and your choice of shoe should be as well. The span of leg between the hem and the laces will not help you to pull off the Brogue look well. Instead, by staying with the more classic trainers (the smarter, dressier types) you will negate thoughts of tennis sessions. Summer specific sandals such as espadrilles, deck shoes and pool sliders are always a winner if you leave the socks at home.




Around 15 years ago, the only option you had at the end of your two piece suit was how much split you wanted visible on your shoes. Designers started to get creative with tailoring and suddenly the suit (in your father’s day, especially) stopped being a uniform and started being something, well, more fun. These days, you can split trousers and jackets as well as breaking early 70´s taboo’s such as wearing your double breasted blazer un-done and you don’t have to complete your final look with Derbies or Oxfords; but, if it’s rather a formal event you should obey some classic protocol. If you don´t fancy conforming to any such protocol, then the new line of unstructured suits that pretty much every design house offers these days, will look just as good with a t-shirt as it will with a collar. This look also fits the street style trend we have been seeing so much of these days of tailoring with white, minimalistic trainers being the ultimate dressing down for traditional dress up´s. A discreet gap between the trouser and the trainer will help you to reinforce this visual boundary between smart and casual.

If your suit has an element of texture (with many options out there ranging from heavy wool, flannel and tweed), you will normally need a heavier type of footwear. Pebble leather boots and classic Brogues will give you that needed lift to raise your style in the right direction.




As the still obeyed rules of Hollywood glamour tell us, you won´t get too much mileage in playing around with the classic black tie look. Thanks to sexy sartorial marketing such as Jared Leto in Gucci, you can throw cyan velvets and embroidery into the equation upper body, but a solid pair of shoes will help keep you to keep your style on a great foundation. If you do want to rock the black tie boat then a pair of velvet or patent leather bowed slippers will work a treat (especially if you match the texture to your bow tie). You can also throw in a little visual interest by opting for the embroidered upper styles that are so favoured right now by houses such as Dolce & Gabbana. If you´d rather not attract too many glances on your shoes all evening then the patent leather lace up´s are a fail-proof alternative.



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