Entertainment Fashion & Style The Best Pants to Wear With Men's Boots Share PINTEREST Email Print Fashion & Style Shoes Accessories Tops & Sweaters Dresses Skirts Jeans Pants Outerwear Lingerie & Swimwear Do It Yourself Kids and Teens Bumps & Babies Learn More by Craig Playstead Updated May 23, 2019 There are few things that a man can wear that are cooler than a great pair of boots. Not just for use on construction sites, work boots are appropriate to wear in many situations. They're sturdy and stylish all at once. Here are some of the outfits that work best with men's boots. Jeans Kirstin Sinclair/ Getty Images Nothing looks better with a cool pair of boots than jeans. The Fonz taught us that years ago. Nowadays we have a lot more to choose from than just the black motorcycle boot (which is still cool), but you can also style a pair of desert boots, an upscale work boot, or just a basic black boot with your jeans. Just make sure you're not wearing a pair of black boots with really washed out jeans. You'll look like a superhero... and not in a good way. Jeans are what you should be wearing with most winter boots also. Slacks Kirstin Sinclair/Getty Images Personally, I don't wear a nice pair of dress boots with slacks or a suit, but more fashion forward people would -- and do. It's a much different look when you need to be a little more fashionable while dressing up. Most of us take a more conservative approach when the tie goes on, but if you don't, a pair of dress boots will be a nice addition to your wardrobe. It might also be a nice time to break out a little and try something new. Khakis Ben Pruchnie/Getty Images With so many boots to choose from these days, you won't have a hard time finding the right one's to wear with a nice pair of khakis. Boots that never seem to go out of style are desert boots and they are perfect when you want to be a little dressier than jeans. You can also go with a pair of chukkas. Cole Haan and Frye are two companies that make a killer chukka boot. Continue Reading