Chukka boots are a fashion favorite among men of all ages and styles. Rising just to the ankle with two simple eyelets, this style is one of the most versatile Italian leather shoes you can find. Their clean, utilitarian shape and effortless look are perfect for casual wear but are nice enough to wear with a suit. However, sometimes being spoilt for choice lends to uncertainty. So how exactly do you style chukka boots?

With a suit…

Pairing chukka boots with a suit breaks up the monotony of the run-of-the-mill dress shoes look without being overly risqué. They really look best with a suit in winter when the extra coverage makes sense, but if you’re not one for the loafers-suit pairing anyways, rock your chukkas with a suit all year long. The secret to dressing up chukka boots is to make sure the cut of your suit is as slim as you are comfortable with. If your suit is overly baggy, they will swallow your chukkas making the look no different than wearing it with a pair of wholecut oxfords.  Then again, if you think wearing a baggy suit is a good look at all you have bigger problems than how to wear chukkas. Remember: the tailor is your friend; your tailor will not steer you wrong.

With layers in the winter…

Like we point out above, boots in winter just plain make sense. With a pair of wooly socks, you’re going to be protecting your feet from the harsh cold while looking stylish. This whole idea can go casual to office friendly with the pieces you pair it with. However, it doesn’t matter if you’re wearing jeans or slacks, the pants should hit just below the top of your chukkas. If the pair of pants are a bit longer than that, don’t be afraid to tuck them into your chukka boots slightly. Your chukkas are just another element in your layered look, but just as you want the cuffs of your shirt sleeves to peek out from under your sweater, you want to be able to see the boots.

Just about any way you want with jeans…

We’re pretty sure the popularity of the chukka boot is owed to how well they paired with everyone’s favorite kind of pants: jeans. From skinny to relaxed, they look good with just about every cut available. Try cuffing the hems of your jeans to create a bit of eye-drawing contrast to your favorite boots and balance the whole look with a blazer over a button down to make sure the whole look is proportioned. Or just let them graze over the upper and wear with your favorite broken-in chambray for a devil-may-care look.

Need a pair of chukka boots to complete your collection of Italian leather shoes? The Newman Chukka Boot comes in four stylish colors that look great no matter how you want to style them. Get yours here.