How To Wear Men’s Boots 101 – 5 Best Boot Styles: Chukka, Chelsea, Jodhpur, Balmoral & Winter Boots

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Unfortunately, there’s not one boot that works for everybody because we all have different needs and preferences.

1.Chukka boot or desert boot
A great boot for students. You can invest in one pair of boots and it works with a lot of combinations. It’s also a fantastic boot for men who like to wear denim or jeans. It’s a boot that pairs well with corduroys when it’s cold outside during fall & winter, or with khakis when it’s warmer outside.

I suggest you go with a dark brown, a choco brown, or a mid brown because it’s most versatile. If you wear a lot of suits, it’s not the boot for you because it’s very suited to casual outfits.

2. Jodhpur boots.
Personally, I like them a lot because they have a very clean, elegant silhouette yet, they have some history. The characteristic of Jodhpurs is the buckle and it goes around.

I think it works really well with casual suits, flannel suits, and sport coat combinations. You can also pair it with a leather jacket or jeans, or chinos. Because there’s no broguing and it’s a flat boot, you can also pair them with a regular suit. It’s great for men who like clean, classic, elegant lines and you don’t just want to buy a boot anybody else has.

Ideally, a mid brown or something lighter, maybe tan, works best and it’s most versatile. If you’re in a hurry and you don’t have the time to buckle the boot every time and take it off, it’s not a boot you should go for.

3. Chelsea boots
A timeless classic because they have that insert and it’s easily recognizable especially if you have a colored insert just like here.

They’re perfect for men who look for a convenient, easy slip on version of the boot. Even though they’re quick to put on, they are super elegant and classy and don’t look sloppy at all. They’re also great for eccentrics because you can add green, red, or blue inserts that really give you a personal note.

I believe every man should have at least one Chelsea boot in their wardrobe because they are so timeless, versatile, and easy to use.

4. Balmoral boot
It’s a classic dress boot that works well with formal outfits.

It’s basically the choice of elegant gentlemen who want something like an oxford shoe as a boot version. It’s a fantastic boot if you have lots of formal outfits in charcoal, navy, and grey. It’s also fantastic with three-piece suits or you can wear it with a morning coat, or with a stroller suit.

I suggest you start with black with black suede insert. If you are more advanced, you can have a contrasting insert in beige or buff or off-white and if you have that, you can move on to something in brown, burgundy, or other colors.

5. Winter boots
If you live in a climate where it gets close to freezing outside, you need winter boots. They may just look like regular boots but they have a wonderful fur lining. With fur, I usually mean sheepskin or lamb skin. It’s quite plush and insulating and cozy warm especially if you’re outside a lot when it gets cold.
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