The Best Timberland Boots and How to Wear Them

how to wear timberland boots men
PHOTO CREDIT: Cool Artisan

If you don’t own a pair of Timberland boots, we’re are to change that. They are one of the most versatile styles around, and believe it or not can be dressed to suit many occasions. So here’s how to style them.

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How to Wear Timberlands

I can hear the uncertainty from some of you about this one, but the Timberland boot is definitely something everyone should own. It was popular during the nineties amongst the hip hop and rap community, and if you’re imagining celebrities wearing Timberlands for instance a 1999 Jay-Z with wide-legged jeans and a New York Knicks jersey wearing his boots, we can assure you those days are over.

At the beginning of the new millennium, the brand started to fade out – probably because of its over-saturation in the market– it became a clear-out item and lost appeal by the mid-noughties. But, you can’t keep a good boot down as they’re now being worn by many. They can be worn to complement a nice pair of jeans rather than being used to stomp along the pavement in a pair of oversized trousers. The resurrection of the Timberland style has seen it play a lesser role in popular culture and has is being seen as a good alternative to a Chelsea boot or chukka for a casual occasion.

A Casual Day Out

Yes, you may consider it as a throwback to the days when Timberland boots were your chosen footwear for every occasion. But when we say casual, a Timberland casual look pushes the very boundaries of how dressed down you can be. You wouldn’t wear Desert boots and sweatpants so we wouldn’t recommend Timbs and sweatpants either – well, baggy ones anyway. If you want to wear a pair of joggers with your Timberlands then they need to be right. Keep them black and keep them slim fitted, not skin tight and not baggy. They also need to be a fairly good, thick material like The Idle Man own brand pairs. Wear these with a T-shirt, hoodie and bomber jacket. Layering is key here, so make sure your colours match.

The First Date

These shoes can be intimidating because of their solid nature and really eye-catching design. But with the right attire, you can actually impress in them on a first date. As long as you’ve got a great sense of style you’re half way there. Take a pair of dark coloured Timberlands and pair them with a coach jacket and slim fit jeans. If you feel like you need to be a bit smarter, a simple grey or navy overcoat will make the boots feel like they belong with your outfit.

mens grey overcoat look
Timberlands can be dressed up to look fairly smart


Dress Down Boots

When it’s time to relax a bit from the regular nine to five attire of a suit and smart black shoes, dressing down can be easy. So when it comes to the dress down days at work, Timbs can work a treat. You can’t really go over the top and wear whatever you want, as you are still an employee of that company, but with a smart casual shirt and black chinos you’ll be ready to go out for Friday night drinks straight from the office. And from there, who knows where you’ll end up, but either way your Timberlands will get you there.

Timberland Boot Colours and How to Style Them

Black Timberland Boots

A pair of black Timberland boots are equally as classic as the better-known sand colour. However, over time these are the ones that have been updated with more of a modern twist. The iconic 6-inch Timberland boots have been given a new design with the use of a durable football leather. Plus, the gold eyelets on the design are perfect if you want to add a bit of street to your look. Try pairing with black jeans and a white logo T-shirt and you’ll have a simple outfit ready for the weekend.

mens timberland 6inch premium boots look
All black Timberlands are a must


Red Timberland Boots

Now if you like a bit of colour, then this style is the one for you. Remember when introducing colour make sure your outfit base is quite simple. Think white shirt and blue jeans, with a slick black jacket. If you want the ultimate street look then wear all black with your red Timbs. This will give you instant style points and you’ll stand out from the crowd.

Blue Timberland Boots

Now with this colour, it’s important to incorporate a few different shades into your outfit but never too bright. This tonal look is very eye-catching but is also laid back enough that you don’t feel too extra. Blue always looks nice with black pieces (as do most things) so think about what accessories you can wear to anchor the look.

Green Timberland Boots

The green Timberland boots are the easiest to slot into your wardrobe as the neutral tone of them means they sit nicely with other colours. A camo pair is really key for this season and would look great styled with dark denim jeans and a classic khaki jacket. The khaki trend has been around for a few years now and there doesn’t seem to be any signs of it coming to a halt, so a pair of green Timberland boots will work wonders in your wardrobe.

How to Clean your Timberland Boots

A we come to the end of our style guide, one thing that’s important to remember is that you should take care of your Timberlands. If you’ve invested in a pair of Timberland boots, then go that extra mile and get a suede or leather cleaner to make sure the boots stay looking new for longer. The fresher they look, the better they look, so it’s worth investing in a good cleaner.

Best Timberland Boots and How to Wear Them

  • Think about the style you want to go for. Is it the classic tan, black or do you want something with a hint of colour?
  • Timberlands can look casual so if you’re dressing them up make sure you keep a smart casual vibe throughout.
  • The chunky style means you shouldn’t wear bottoms that are too skinny. Keep things slim fit and not overly baggy.
  • Before you wear your Timberland boots, spray them with a shoe protector to avoid marks and stains.
best timberland boots and how to wear them for men
Timberlands are easy to wear and style so it’s worth investing

On That Note

Go forth and rock this seasons trend without feeling dated. Just remember to avoid anything too baggy and you won’t look like you’ve stepped out of a 90’s Puff Daddy video set. Timberlands are a great autumn winter essential, so getting your hands on a pair of these will take through every season, no matter how cold it gets.

Author: David Warren


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