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How to Wear Ankle Boots for Men?

So you've got your new favorite pair of ankle boots. Now how do you wear them?

Ankle boots are a fun style of men's boots because they're so versatile. You can wear ankle-high leather boots with jeans and a t-shirt or dress up some suede boots for a smart-casual style. All you have to do is pick your boot style and get started planning amazing new outfits.


Ankle boots are a great base for any casual outfit. They can easily be dressed up and down, and there are styles available for all occasions.

Looking for how to wear ankle boots with skinny jeans? Bring a new element of style by learning how to tuck jeans into ankle boots. Wear skinny jeans over flare jeans for tucking, since they won't bunch when you tuck the hem into the top of the boot. Pair some black leather waterproof boots with a plain tee and a leather jacket or bomber jacket for a cool look that spans the seasons.

Need to know how to wear ankle boots with straight-leg jeans? Some dark jeans and a dress shirt bring an everyday look to a new, more dapper level. Or, you can pair your work boots with standard blue jeans for the perfect everyday men's style.

Figure out how to wear short boots with jeans. Cropped jeans are perfect for showing off lace-up boots that end at the ankle. Short-profile chukka boots are the perfect casual boot and can be your go-to men's fashion staple.


It's not all loafers and Oxfords at the office. Our high-quality dress boots are perfect for a business casual look that brings you into the 21st century. You don’t need to wear uncomfortable, pinching dress shoes. Instead, create an approachable business look.

Modern gents looking for how to wear ankle boots with dress pants will love our soft-as-suede Chelsea boots that match great with chinos or other menswear pants. These leather Chelsea boots add an approachable sense of style to your smart-casual look.

Can you wear boots with a suit? We're here to solve this age-old question with a resounding yes. There are certain types of boots that are great with dress pants. If you’re wearing a suit in black or grey, some black boots can be the perfect pair of dress shoes to match your blazer.


Build your own laid-back style or go for a high-fashion look. Whatever outfit ideas you want to bring to life, we've got the pair of boots to do it.

Need to know how to wear ankle boots with pants? It's easy to pair some dark wash jeans or skinny pants with Men's Timberland® Heritage 6-Inch Waterproof Warm Lined Boots. Even when the weather takes a turn, these boots can double as hiking boots or winter boots for any kind of outing.

When you're looking for how to wear short boots with skinny jeans, look no further. Simply tuck your hems into some moc-toe boots or combat boots. You can pair this look with a comfy cardigan to stay relaxed all night or layer a button-down over a solid t-shirt for a casually classy look.


There are plenty of ways to show off the best boots in your wardrobe. Style with black jeans against light boots or pair a light wash with dark leather boots for contrast. Tuck just the front of looser-fit jeans into the tops of your boots to show off the front lace-up style. You can choose to lace up your boots traditionally, or leave the laces undone for a casual style. 

Turn an older pair of jeans modern by cuffing them (rolling the cuffs up once or twice) to show off your ankle boots properly. Double cuff even wide leg jeans to show off taller boots.

You can even pair your Timberlands with shorts and some crew socks for a summertime look. Casual Timberland boot styles work best with this look, so grab our iconic original Yellow Timberlands and wear them with just about anything you like, from sweatpants to shorts.

There are just as many ways to wear Timberland boots as there are guys who buy them. Shop Timberland now to build your own unique style. And don't forget to add yourself to the mailing list to hear all our latest news!