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.