5 Rules For Men’s Boots Styling (And 2 BIG Mistakes) (2024)

5 Rules For Men’s Boots Styling (And 2 BIG Mistakes) (1)

Let's get one thing straight: I freaking love boots. They’re great looking, comfortable and versatile when it comes to men’s boots styling.

I love them so much, that I own several pairs. They're my go-to shoe.

Time-after-time, though, I see men's boots get misused and abused. The simple fact is that a lot of guys do not have the knowledge to rock them as best as they can.

That's why I decided to write today's article, gentlemen. I'm giving you a CRITICAL rundown of some key rules to be aware of when wearing men's boots.

All the great-looking boots you'll see here are made by Thursday Boots, the paid sponsor of today's article. I've been wearing and loving their boots for over two years – these are quality boots at an affordable price.

They use water-resistant Goodyear welting, leather from Tier 1 USA cattle that develops a beautiful patina with time, and a cork lining that conforms to your foot for comfort. Click here to find your favorite Thursday Boots.

  1. Know Your Options
  2. Get The Right Type Of Trousers
  3. The Right trouser Length
  4. Knowing WHEN To Wear Boots
  5. The Right Colors
  6. Matching Leathers
  7. Proportions Are Key
  8. NEVER Have Dirty Boots

Men’s Boots Styling Rule 1. Know Your Options

I can't recall any man who wasn't guilty of ignorance when getting into shoes. They'll hit the store, see boots, and buy the first pair on display. They don't realize what different kinds of boots can bring to the table.

For instance, a Chelsea boot is a fantastic addition to a man who is trying to err on the side of elegance. It's sleek, smooth, and simple. It's also easy to slip on and off! The Chukka boot, however, is far more rugged. Off the bat, we can see open lacing we tend to see on a shorter Blucher or Derby

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While it can be worn in similar contexts to the Chelsea, it gives off a hardier vibe. The fact that it comes off a long military history contributes to this as well.

You can also find dress boots with closed-lacing systems that resemble an Oxford in appearance. Trust me, the options are almost limitless.

Men’s Boots Styling Rule2. Pick The Right Type Of Trousers

This concept is fairly simple, gents, so I won't dwell on it for long.

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Dress boots do not go well with more formal trousers for reasons I will go into more detail down below. Stick to jeans and chinos as much as possible. As a general rule, avoid slacks and suits.

Your choice of pants can either elevate or diminish the impact of those stylish boots. For a classic look with Chelsea or chukka boots, opt for slim-fit or tapered trousers that gracefully showcase the boot's silhouette.

If you're venturing into the rugged terrain with work boots or combat boots, consider straight or slightly relaxed-fit jeans for a balanced aesthetic.

Remember, the harmony between boots and trousers is a style symphony – get the pairing right, and you're ready to stride with confidence.

Men’s Boots Styling Rule3. Find The Right Trouser Length

Even if you know which pants go well with men's boots, it means nothing if they're too short or baggy.

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Generally speaking, your trouser hems should graze the top of the boot for the best look. It should be about1/2 to 3/4 of an inch above the ground.

Men’s Boots Styling Rule4. Know WHEN To Wear Boots

Even if a pair of men's boots look AMAZING. Even if they look sleek, elegant, all-around perfect… They DO NOT belong in a formal outfit.

Boots are fundamentally casual. They come from rugged roots, and that's embedded in our perception of them. That's why you should only wear them with jeans or chinos. NEVER wear them with a formal suit, and certainly not for black tie.

Men’s Boots Styling Rule5. Find The Right Colors

Despite the casual nature of men's boots, colors still matter when it comes to rocking them right. You'll find them most commonly in black and brown.

The same principles apply here as they do in all things stylish: Black is more formal than brown.

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While you'll never achieve formality with boots, you can still shoot for something a little more streamlined with black. Meanwhile, you can rest easy knowing that brown will always serve you in the most laid back situations.

Men’s Boots Styling Rule6. Match Your Boots With Other Leathers

Gents, simple tip here. As with all shoes, you should strive to match them with your belt and any other leathers you might be wearing (a watch, for instance).

You should match your leathers, but this rule can be broken if you know it well.

Now, there is an exception. Suede does not necessarily have to match the other leathers in your outfit. You have more freedom to play around here.

Men’s Boots Styling Rule 7. Proportions Are Key

What do I mean by this? Every piece of clothing you wear should be cohesive in terms of size.

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This means that if you're wearing sleeker, smaller boots, then you should avoid bulky trousers. The same goes for pairing large combat boots with very slim jeans – it just makes your feet look bigger.

The Mistakes…

Yes, gentlemen, it's time to find out what you're doing wrong.

Men’s Boots Styling Mistake 1. Dirty Boots

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This is a HUGE no-no. It certainly applies everywhere, but so many guys neglect their shoes. Gentlemen, make sure that you care for your boots. I advocate for shining them after each wear, but you should at least set some time aside for them each week.

Remember that cleaning traditional leather is not the same as suede. Leather requires polish and moisturizer, while the same ingredients would ruin suede.

Men’s Boots Styling Mistake2. The Difference Between Leather & Rubber Soles

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Lots of blogs and stores advocate for leather as a better-quality material. Strictly speaking, yes, leather is going to be harder to come by and therefore more expensive.

Practically, though…

Leather Soles are less practical than rubber soles on boots.

If you're going for something as rugged as a boot – something that's going to serve as a badass addition to your casual closet – then why not go rubber?

If you take to a slippery street in leather soles, you're liable to fall on your ass. No one wants that, right? Consider rubber!

For the modern man, understanding the art of wearing boots is more than a style choice—it's a statement. The key lies not only in choosing the right boots but also in pairing them with the perfect pants.

Whether it's the sleek lines of Chelsea boots or the rugged charm of work boots, knowing the nuances of matching trousers is paramount.

Fit and occasion matter; slim trousers complement dressier boots, while relaxed fits harmonize with more casual pairs. So, gents, step into each occasion with confidence, armed with the knowledge of how to wear your boots right—it's the mark of a true style maestro.

Summary – Men's Boots

  1. Know Your Options
  2. Get The Right Type Of Trousers
  3. The Right trouser Length
  4. Knowing WHEN To Wear Boots
  5. The Right Colors
  6. Matching Leathers
  7. Proportions Are Key
  8. NEVER Have Dirty Boots

See, gents? Boots can contribute significantly – whether you're in business casual or in a T-shirt and jeans. Never underestimate their power.

Just like in all things, though, there are rules to follow that let you make the best of what you have.

5 Rules For Men’s Boots Styling (And 2 BIG Mistakes) (2024)
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