Traditional does not need to be synonymous with boring, and if there’s a suit that proves it, it's the classic pinstripe. With its thin or wide pinstripe running throughout, these suits are a slick spin on traditional. First rising in prominence during the Jazz Age and Gilded Age before it, they have always had a touch of glamour, decadence, and mystery about them. Although these suits are a typically regarded as formal pieces, they can be just as playful as they are elegant—the key is in knowing how style them.

Let’s begin with why and when you should wear this garment. Pinstripe suits are unmistakably formal and typically not great for a casual experience or event. However, some are disregarding this convention these days. If you’re one of those contrarians, we advise that you wear a pinstripe suit when you wish to stand out in a crowd. If not, we advise you keep the pinstripe for formal events. Now, how should you wear that pinstripe suit? If you’re wearing a pinstripe suit to a formal occasion, you should stick to a formal look; a properly-fitted dress shirt and a well-assorted tie are great pairings. If you decide to sport a pinstripe to a less formal event, consider breaking up the style with a turtleneck or v-neck t-shirt.

This will temper the overall tone that the suit exudes. Important to note, is that unlike unicoloured suits, it is ill-advised to wear the suit jacket or pants as separate pieces. The vertical lines of the pinstripe are meant to evoke length and height, and when worn separately, the pieces give an incomplete appearance to the look.

Why would you want a pinstripe suit? For variety, mainly. If you already have a staple suit collection—we’re talking blue, black, and grey suits—a pinstripe is a great addition. Otherwise, as mentioned, the pinstripe is meant for more extravagant events. You can really clean up nicely in a pinstripe suit when you pair it with the right dress shirt, tie, and other accessories, such as a watch and dress shoes. Adding a vest also immediately kicks the suit’s look up into the highest categories of formality and style. Leaving this out, but adding cufflinks and a contrasting tie could also have this effect. A good rule of thumb for a pinstripe is this: the less you wear, the safer the choice you’ve made. The more you add, the bolder the look.

Let’s discuss colours. In terms of colours, we’d recommend you stick with navy, black, and grey until you know what you’re doing with a pinstripe. These three staple colours are always in style and are easy to pair with shirts, ties and other accessories. For black pinstripe suits, you should probably keep in mind formality and where you’ll be wearing the suit. This would be great for work or an after-hours event and even a formal occasion. That said, if you rarely attend formal events and don’t really want to cut a bold look, we’d stay away from the black variant as it is perhaps the most limited in its application. Perhaps a good alternative in this case would be the navy pinstripe suit, as it is similar to the black one, but is more flexible in terms of where you could wear it. The grey pinstripe, perhaps the most versatile of them all, tends to allow you the most flexibility, which is why we love it. If you want a suit that looks smashing, and don’t only want to wear it on occasion, the grey pinstripe suit is the one you need. Other colours, such as blue, allow you some more flexibility as well, but you should keep in mind that the more exotic the colour, the more likely you are to stand out.

Now, let’s discuss stripe width. There are lots of the options out there when it comes to stripe size, which might be daunting to some, but this shouldn’t scare you away. In general, the wider the stripe, the bolder the look. As we’ve mentioned, a good rule of thumb for pinstripe suits is that the more elements you add to it, the bolder it is, regardless of colour. This rule can be transposed to stripe width, as well as suit colour and fabric.

A moderate style is the chalk stripe—a thin white line down the paint. It’s an easy stripe to get started with, especially on staple colours, such as charcoal grey, black, navy, or blue. Once you’ve figured out what you like, you can begin exploring pinstripes of more varied colours andstyles to see what they do for you. Wider stripes are often associated with Wall Street and the “powersuits” of the 1980s. If you like a bold stripe on your suit, we advise that you keep your accessories and shirt free from design and in solid colours to balance out the overall construction.

Overall, a pinstripe suit is a staple of the modern man’s closet. We recommend you own at least one in the colour and style that you enjoy most. While there are rules when it comes to the pinstripe, anyone in fashion can tell you that the sartorially minded know how to break themand remake them to create a new look.