What Can You Wear With Timberlands? (What Looks Good With Timbs?)

What can you wear with Timberlands? Can you wear them with sweatpants? Can you wear them with shorts? Can you wear them with skinny jeans? Can you wear them with a dress? Can you wear them with leggings? Let’s find out…

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Maybe you just bought a pair of Timberlands and you’re wondering what you can wear with them, or maybe you just don’t know how versatile the once outdoor-only boot actually is.

Timberlands are a unique shoe that can be worn with a variety of outfits. You will find that they go with a lot, but there are some combinations that may not work as well.

What Can You Wear With Timberlands?

Timberland boots can look good with everything from skinny jeans to denim shorts. Timberland boots are pretty versatile. You can wear them just about anywhere and look great. The only thing that really matters is what you’re comfortable wearing.

Timberlands are a wonderfully versatile boot that pairs well with a variety of styles, including:

  1. They look great with denim or canvas pants and shirts.
  2. Pairing Timberlands with a worn leather jacket or short fall or winter coat and scarf is also a very classy style.
  3. In the summertime, Timberlands are the perfect accessory to a simple T-shirt and jeans.
  4. In the fall, Timberlands can accent a comfy flannel with pants or a nicely made sweater and khakis.

These boots make a rugged and classic addition to any look and are not only stylish but functional.

Do Timberlands Go With Anything?

Timberlands go best with a more casual style. Most people will wear them with jeans and a button-up shirt or plain t-shirt. If you want to dress up the look a little bit, you can wear a blazer or long coat to upgrade the outfit. However, Timberlands don’t fit very well with a more formal outfit such as a suit.

Some of the most common outfits to wear with Timberlands are:

  • Slim jeans with a t-shirt or flannel button-down.
  • Slim-fit Cacies with a denim or chambray shirt.
  • Black jeans with a plain t-shirt and a blazer.
  • Dark jeans and a pull-over sweater

Can You Wear Timberlands With Leggings?

Leggings go very well with Timberlands since Timberlands are a bulky-looking boot, so having bottoms that are more form-fitting helps maintain your silhouette. Leggings or slim-fitting jeans are usually the best choices to go with your Timberlands.


Timberland Women's Tillston 6 Inch Double Collar Ankle Boot, Black, 8


You can add other casual pieces to your outfit to pull everything together. Here are some outfit ideas for when you want to wear leggings and Timberlands:

  • Dark or leather leggings with a denim jacket.
  • A playful dress and cargo-inspired overshirt.
  • A Jersey and some Aviator sunglasses.
  • An over-sized hoodie or pull-over sweater.

Can You Wear Timberlands With Shorts?

It takes a certain style and personality to pull off wearing Timberlands with shorts, but some guys can pull it off.

Jean shorts work best with Timberlands, but you can wear athletic shorts or even cargo shorts with Timberlands as long as the color of the shorts complements the color of your Timberlands. The color of your shorts should never match the color of your boots.


Timberland PRO Men's Hyperion 6 inch XL Alloy Safety Toe Waterproof Industrial Shoe, Brown/Black Distressed, 10.5


Timberlands with shorts look best in an outdoor setting. Therefore, if you are camping, hiking, or doing some sort of handy work feel free to use this combination. Timberland and shorts aren’t often seen as a fashion statement, but the right color combination could look stylish.

Can You Wear Timberlands With Skinny Jeans?

In general, Timberlands look best with tapered pants, which helps them minimize the overall bulkiness of the look.

For this reason, skinny jeans are the perfect accompaniment to Timberlands, but you’ll want to ensure that your legs don’t end up looking too skinny.

If you want to pair skinny jeans with boots and keep your look stylish and balanced, try the following. Roll up your jeans into a cuff that sits just above the boot line.

If you can’t get that to look quite right, try instead, pulling your jeans up slightly so that the material bunches a little above the ankle, giving some extra bulk to the skinniest part of your leg.

People avoid wearing Timberlands with jeans because the contrast between the bulky boots and the tight-fitting pants can look unbalanced. To even this up, try wearing an oversized shirt to compliment your look.

Can You Wear Timberlands With A Dress?

Timberland boots can be worn with a dress as they are a classic wardrobe accessory. They are a great choice for both the winter and the summer months, as they can be styled with almost any outfit – from summer dresses to winter trousers to anything in between.

A dress is a great option for wearing with your new Timberlands. A simple sundress or even a maxi dress will look great with your black or brown Timberlands.

Timberland boots are extremely versatile and come in all shapes and sizes. They are available in almost every color and every style, and are a great everyday choice to be worn in any season with any outfit. Timberlands will forever be a timeless fashion accessory!

Can You Wear Timberlands With Sweatpants?

Simply put, of course, you can wear Timberlands with sweatpants. Unless you are going somewhere that has a dress code, you are free to dress however you want to.

Differentiating Between “Can” and “Should”

As for whether or not you should employ that combo, the answer is definitely no, but that’s mostly because sweatpants are not looked favorably upon as a fashion statement.

If you just want to be comfortable, feel free to wear sweatpants and Timberlands, but if you want to look good according to public standards, you definitely should choose a different ensemble.

In summary, Timberlands were originally designed for rough, outdoor work. And while they’re as durable as ever, they’re also worn as fashion statements by people of all ages.

You may also be interested in… Can You Wear Boots Business Casual? (Are They Office Appropriate?) and Are Timberland Boots Worth It?