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What to Wear With Grey Boots for Men?

A pair of grey boots are a popular style staple, and it's not hard to see why. Unparalleled in their versatility, grey boots pair well with anything from tees and joggers to skinny jeans and a black leather jacket to a more formal blazer and chinos.

If you're wondering what to wear with grey Chelsea boots, the answer is basically anything. The ideal foundation for any menswear capsule collection, you can easily dress them up or down for a casual look.

How do you know how to style grey Timberland boots, and what are the best boots for your needs? Let's explore what to wear with dark grey boots for any occasion.


How you style grey boots depends on the level of formality you'd like to achieve in your look. For instance, grey ankle boots without laces tend to be more formal when paired with a blazer and camel coat. However, they can be easily dressed down with a hoodie or leather jacket.

If you're curious about how to wear grey chukka boots or level up your snow boots in style, here are a few classic outfit ideas to consider:

  • A jacket is a must: If you're not quite sure where to start, you can't go wrong with a jacket and grey suede Chelsea boots.

  • Blazer and boots for the win: A grey or navy plaid blazer and dark jeans would pair well with our Men's TrueCloud Sneaker Boots. For an added pop of color, opt for the Men's Davis Square Chukka Boots instead.

  • A green parka with grey boots: For a fresh take on a classic, pair a dark green parka with black cargo pants (or a green parka with white cargo pants works, too) and top off the look with grey ankle boots.

  • Ripped jeans and work boots: Pair black or charcoal ripped jeans with a long-sleeve shirt and the Men's Hi-Vis Timberland Heritage Boots. A classic work-boot design is engineered for optimal comfort and traction, while bright orange laces add a pop of color.

  • Denim on repeat: Pair a light blue denim jacket with leather or suede Chelsea boots in charcoal for a smart casual look.


If you're wondering how to style grey ankle boots, we've totally got you covered. What you wear really depends on the look you're going for. A more casual boot outfit for men might include a t-shirt paired with a bomber jacket and sunglasses.

If you're aiming for practicality without sacrificing style, pair your boots with a dark green or black parka and cargo pants.

For a sleeker approach, consider wearing Timberland boots with a camel jacket and navy or black plaid chinos. Do grey boots go with everything? We believe they really can work with any wardrobe.

Shop Men's Boots at Timberland today to find the perfect pair of grey ankle boots for you. Then, transition from work to the weekend in serious style.