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The ultimate guide to wearing boots with shorts for men

When it comes to must-have footwear for men, if boots are at the top of your list, this article is for you. We love boots as much as you do, and why not? Ultimately, not only are boots practical and comfortable, but they’re also versatile and stylish. A pair of smart leather boots can take you from work to the weekend with ease as boots look well with smart casual as well as semi-formal ensembles, making them a valuable wardrobe addition.

Having said that, not all boots suit all outfits, for example, pairing boots with shorts is a really tricky game. The warm season is almost upon you and if you love your shorts, it’s important to familiarise yourself with the different types of boots that go well with shorts and the best ways to style them. Urban Shepherd Boots is a small, family-owned workshop in Benedita, Portugal which is born out of pure love for leather shoes and we are here to show you exactly how to wear boots with shorts for a sleek and fashionable look.

A ‘Short’ history

Shorts for males originated as a part of school prep for children in the 1880s. That was the only purpose of shorts in kid’s lives when they really wore shorts outside of athletic events. In the coming decades, adult men adopted these airy, short and comfortable bottom wear. However, there are quite a few men out there who feel shorts are not appropriate to wear for grown-ups. During World War I and World War II, shorts were brought into military uniforms and that is when men became accustomed to enjoying the benefits of wearing them. This was also the time when men started pairing combat boots with their uniform shorts. Soon afterward, fashion designers started bringing men’s shorts to the masses.

When To Wear Shorts and Boots Together

If you are going hiking, it is always fine to wear whatever shorts you want with your hiking boots. But, in any other scenario, then it is generally considered a fashion faux pas. When you want to step out wearing shorts with boots, remember these two rules:

1. The temperature outside should be hot: You should also keep a check on your environment since your location plays a key role in deciding that as well. For example, in areas like Bermuda, wearing shorts actually with a blazer and jacket is pretty common.

2. You shouldn’t be conducting a business or attending any formal event: Fashion pros in the entertainment industry sometimes can get away with this but if you are conducting a sophisticated and formal ceremony, you need to wear trousers.

How To Wear Ankle Boots With Shorts

Ankle length boots are one of the most versatile types of boots around for men. Thanks to their minimal appearance, these boots suit a range of outfits, including smart casual looks. To rock a pair of ankle boots with shorts, you must first select your boot style. Chelsea ankle boots are a sleek and easy option, on the other hand, Chukkas and other lace-up styles can also pair well. Once you’ve chosen your boots, pair them with shorts and a button-up shirt or roll-neck sweater. To wear Chelsea boots at their best, try choosing a brown or suede pair. Alternatively, select a pair of black or burgundy leather Chelsea boots and wear them with a short-suit.

How to Wear Lace-Up Boots With Shorts

Feeling tough? Why not add a pair of combat boots to your outfit? These classic boots, which appear similar to those worn by soldiers, instantly add a rugged touch to any ensemble. Perfect for casual outfits and weekend outings, combat boots look best when teamed with other edgy designs. To nail the look, stick to a dark color palette and opt for heavy-duty fabrics, such as denim and leather.

How To Wear Desert Boots with Shorts

Also called the Chukka Boots or Chukkas, these boots are recognized as the cool, casual essential in any man's wardrobe - just like shorts. Addition of some desert boots can instantly change your whole casual look. This combination of Chukkas+Shorts offers a unique aesthetic that other shoes cannot. No man’s footwear collection is complete without at least one pair of desert boots. Pair these boots with a tailored shirt and chino shorts for a rugged yet modern look. Throw on a light sweater or jacket when it gets cold and you can happily transition from day to night with ease.

Consider adding these boots styles to your wardrobe and get different looks with each one. To summarize, ankle length boots with shorts will impart a  modern, streamlined touch to your business look; Chukka or Desert boots will give you a cozy, comfortable look; and a pair of lace-up boots will look versatile with shorts.

Shorts and Boots may seem like an odd union, but it can work. Don’t be afraid to try something different this year!

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