Men’s fashion is completely different from women’s fashion. While a pair of colorful rain boots can look cute and fashionable on women, it is much harder for men to combine rain boots into a decent outfit. While Hunter boots have become very popular with women, it is difficult to find men wearing rain boots although they should have the same opportunity to use these practical boots and look fashionable at the same time.
Tall boats, low boots, or technical boots?
My advice for women on what to buy was straightforward: go for the most iconic tall boots that represent the Hunter brand the most. For men the advice would be slightly different: pick either a pair of tall boots or give the short boots a try. Either way forget about the Chelsea boots as they seem to be an odd combination of rubber waterproof shoes suitable for sunny weather, as shown below by digital director Steven Rojas (picture by Hunter boots).

When you go for the tall boots there is the choice of the Original tall boots which are available in mostly darker colors, and the technical boots which have a more rugged and adventurous look. You can best combine the tall boots with tighter fitting designer jeans, while the technical boots go great with workers jeans that are a bit baggier. I prefer to see the technical boots being used for real outdoor activities while the original tall boots are better in an urban setting. The picture below comes from tiso.com:

Short boots are more easily to put on and off and would do well with a similar clothing style as the technical boots: something less sophisticated and more workmen’s wear. But these boots would fit well to a city dweller .

Matt or gloss, and what color
The question matt or gloss can be easily answered by pointing out that the men’s range only has matt boots available, but since the women’s and men’s boots are basically the same besides the sizes, it all depends on personal taste. A pair of gloss boots will give a dressier look than matt boots, so make sure to combine them with a bit more sophisticated clothing to get a matching outfit.

Go for the black or dark colors, but again there barely are lighter colors available in the men’s range. It is possible to buy a more colorful boot from the women’s range, but this is a look that is extremely hard to pull off successfully for men. Good looking men, like Nick Grimshaw pictured below, who put a lot of attention in their outfit still look kind of awkward in bright colored boots.

Sizing
Even though Hunter boots are true to their size it is recommended to try on a pair before purchase. Make sure there is enough space around the calf as rain boots should be worn over your pants. Hunter has several adjustable boots available where you can increase the calf size which is perfect for the better trained men.
How to wear Hunter rain boots
In urban settings only wear your rubber rain boots when the weather dictates it. While a pair of boots can look cute on women wearing skirts or shorts, men should always combine them with long pants, preferably skinny pants for a fashionable look or workers pants for a rugged look. Do make sure to get most of the pants in your boots as you want to avoid a bulky pileup of fabric just above the boots. For men avoiding skinny jeans it is recommended to stick to the Hunter technical boots or the short boots. Or, alternatively, adjustable rain boots would be perfect as you can make the calf size larger.

In a more rural setting a pair of working pants in combination with technical boots will give a professional look while keeping your feet dry in every circumstance. But don’t forget these boots are not true working boots with reinforced toes, so in case of dangerous work you better switch to real work boots for safety.

For men it is better accepted to leave the boots a bit dirty, although you should not overdo this. When your boots are covered in mud you will need to tidy them up for urban settings, as nobody wants you leaving a trail of dried up mud everywhere you go. But smaller splashes of mud and stains are perfectly acceptable for both the technical and original tall boots.