Wear It Now: Styling Your Jeans with Boots


Any guy’s wardrobe during the cold months of the year often boils down to some solid tried and true essentials. For myself, that includes a light and dark pair of jeans, a few chinos or khakis, and a couple pairs of nice boots. I always like to keep about three pairs of boots around – a casual, versatile pair for daily wear, a pair reserved for especially rainy or snowy weather and a nicer pair that I can wear dressed up when the occasion calls.  For the sake of variety, I mix them up and wear them interchangeably with all of my pants and jeans throughout the winter.

The thing about boots, though, is that they can often be tricky to wear with different types of pants. Some of them are bulkier and built to last and keep out the weather, while others are sleeker and meant to be kept dressier and more tailored looking. So I figured now was a great time to throw out a few ideas on how to style your pants with different styles of boots.

Typically when I am wearing my bad weather boots, it is because – you guessed it – the weather is bad! For me, these boots resemble vintage style work boots like Red Wings. I think jeans with boots like these look great when they’re styled the way they were back during their heyday. I will often times cuff my jeans just high enough that they reach the top few eyelets on my boots.

I like this style for two reasons: It is a cool way to give your denim a vintage edge that pairs well with the style of your boots. It is a casual look, and cuffing your denim to a shorter length is both a cool added detail and a functional one at the same time. If you’re wearing anything you’d like to keep out of the snow, rain or mud, a few cuffs means your denim is a few extra inches away from all of that muck. Even if you aren’t a fan of the look, it’s easy to just uncuff them as soon as you make you way out of the elements. This styling method works well with any fit of denim, but you’ll find getting a nice looking fold or cuff is easier with a slimmer legged jean.

When wearing nicer boots, whether dressing up or not, I tend to pick a pair of jeans that is a more traditional length. I like most of my chinos and khakis to just barely hit the floor on the back of the hem when I am barefoot. I like this length for jeans as well if I am going to be wearing them in a situation where I want to look a bit nicer. It will give them a bit of break, but won’t have that bulky cuff that can look awkward with a sleeker, dressier pair of boots.

Depending on your own personal taste, this can easily be the same pair of jeans you cuffed a few times when wearing them with bulkier boots. If it is a pair like these, then buying them around the length I mentioned above would make them easy to wear both ways (I don’t think any of us here are in the business of buying a pair of jeans or boots that can only be worn one way!).

As with a lot of clothing dos and don’ts, it really comes down to proportions. If you like wearing a more relaxed fit, you probably won’t want to buy them so long that they pool up around any shoe you are wearing. The extra fabric around your ankles can quickly look sloppy unless it’s kept at a reasonable length. You’ll also find that, if you are a person that really likes your jeans to fit as slim as possible, it might be hard to get them to look right with really big boots. I am a big advocate for wearing all of your clothes in fits and sizes that are similar. This way you won’t run in to problems with two things not quite looking right together. Plus, you’ll never go out of style! It’s hard to beat a nice, dark pair of straight leg jeansAnd we know just where you can find them!

It leads me to the advice I give to every person that asks me about “How To” wear anything. Chances are, if you feel like something looks weird, or just “not right,” then it is. It is most important that you are comfortable and happy with the way you look, so don’t be afraid to add your own twist to these guidelines. Hopefully, though, these are some ideas that can get you going in the right direction!