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If you’re wondering why you don’t see more men wearing puffer jackets to the beach or putting sriracha sauce on their ice cream, the answer is simple. Some things simply should not and do not and go together.
The same goes for shoes and trousers. Sure, you’re probably well aware that flip-flops aren’t the perfect foil for a tailored three-piece (unless you want to be forcibly ejected from every wedding/job interview/funeral you ever find yourself in), but other footwear pitfalls are less obvious.
To take the guesswork out of it, here are the most common trouser styles and the shoes you should be matching them with.
What Shoes To Wear With Jeans
Jeans are the default for most men these days. These are trousers that go from weekend to work, and are so ubiquitous they’ve become almost background. Which should mean they go with any shoes. But that’s not so.
Smart jeans exist, but there are no jeans so smart that they look good with smart shoes. Leave denim and Oxfords to indie bands and your boss on a staff night out. Chelsea boots are generally as polished as you can pull off.
If your jeans are the kind of distressed, stacked versions Kanye might wear, they should be worn with trainers – minimalist always works, but chunky, statement styles work well if the jeans they’re with are more sober. Straight, heavy selvedge that harks back to hard men who did hard work in hard denim, however, works better with thick-soled boots than Yeezy 350s.
What Shoes To Wear With Tailored Trousers
A decade ago, the only choice at the bottom of your suit was how much break you wanted on your shoes. Then designers got creative, and the suit stopped being a uniform. Now you can split your jacket and trousers, you can wear a double-breasted jacket undone, and you don’t have to wear black Oxfords or Derbies. Although, of course, you still can – and if you’re heading somewhere formal, you probably should.
If you’re not, you know those white, minimalist sneakers that have been unavoidable for the past decade? Well, they’re tailoring’s new best friend. A slight gap between the trousers and shoes helps accentuate the split between smart and casual.
If your trousers have some texture – think tweeds, heavy wools or even flannel – they require weightier footwear. Brogue or pebble-leather boots provide appropriate heft, or go all in with a pair of boots that look like you might climb a mountain in, even if you’re only heading to the pub.
What Shoes To Wear With Chinos
Preppy trousers deserve a preppy shoe. If JFK might have worn it, then so should you: canvas sneakers 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 Ivy League for you, then brogues add a couple of years to your look. Let the weight of your cotton dictate the chunkiness of the shoe.
Winter fabric deserves an equally robust shoe. Hiking boots are now a trend, even for the kind of man who defines ‘adventure’ as being more than five minutes from a decent martini. Avoid endless eyelets and garish nylon uppers. Stick to the kind of polished leather real climbers haven’t worn for a century. Show them off by rolling your chinos just above a pair of thick, woollen socks.
What Shoes To Wear With Joggers
Fashion is so often impractical that when a trend like joggers comes round – comfortable, affordable, so versatile that you no longer need to think about what to wear every morning – you should hold it close.
Sportswear roots and a tapered cut make them the perfect foil to statement trainers. Feel free to indulge your space-age tastes in the knowledge that those slim, neutral joggers ground the look.
Dressing up options are more limited. High-low dressing might be trending, but there’s a line. Dress shoes and joggers passed it a couple of horizons ago. Chukka boots are about as smart as joggers can stand – suede adds some texture but, since the shoe was invented for playing polo in, they still feel sporty enough that the look doesn’t jar.
What Shoes To Wear With A Tuxedo
It doesn’t pay to play too much with black tie. Even Jared Leto knows that you can try cyan jackets and bejewelled accessories up top, but a solid pair of shoes will always anchor your experiments.
If you want to make a statement, opt for a pair of bowed slippers, in either velvet or patent leather (match the texture to your matte or shiny bow tie). To make it louder, try an embroidered upper.
If you’d rather not field questions about your shoes all evening, stick to classic patent leather lace-ups. Or, in a pinch, mirror polish your Oxfords until they glow.
What Shoes To Wear With Shorts
The majority of shorts are inherently casual. So, as a general rule, your shoes should be too. However, that doesn’t give carte blanche to schlep out of the house having stuck any old battered running shoes on your feet.
The expanse of space between your hem and your laces does not aid your efforts to wear brogues. Instead, stick to trainers – preferably smart styles in premium materials so people won’t think you’re off to play squash – or summer-specific silhouettes like espadrilles, deck shoes or sandals.
If you can’t bring yourself to be shod in anything other than leather, opt for tailored shorts that are cut as well as your suit trousers, which opens up the options to include penny loafers. Just make sure to lose the socks.