How to wear a pinstripe suit

Colours and patterns


Favoured by businessmen and bankers the world over, the pinstripe suit is the epitome of power dressing. Bolder than the standard navy or charcoal two-piece, a pinstripe speaks to an unsurpassed level of confidence and even a hint of swagger.

In contrast to this flashiness though, the suit’s origins are decidedly humble. Originating in the banks of 19th century England, the pattern was a way of demarcating who worked for what bank, each establishment having their own distinctive set of stripes. Since then, the style has crossed the Atlantic (and beyond), adopted by mavericks of every ilk as a way of standing out from the masses. 

Last popularised in the 80s on Wall Street (and later via The Sopranos), the pinstripe is now enjoying a resurgence in the modern gentleman’s wardrobe. Despite its rising popularity though, pulling off a pinstripe suit is no mean feat. Here, we’ll explain the dos and don’ts, demonstrating how this bold style can be the perfect way to elevate 9-5 dressing and more.

Why you should own a pinstripe suit 

You may well be asking yourself ‘why?’ You’ve already got the basics covered with a few navy and charcoal suit options in the wardrobe. Why do you need to add a pinstripe specifically? 

The answer lies in this suit’s curious hybridity. Fancier than a windowpane check or a houndstooth, a pinstripe suit ups the ante on your standard work attire. And it doesn’t stop there either. Versatile outside of a corporate setting, pinstripes today are increasingly worn as cocktail attire or even for more casual events. 

Beyond this, there’s also the simple ‘stand out’ factor. In a sea of uniformity, a pinstripe suit ultimately provides the wearer with a sense of uniqueness and sartorial nous. There needn’t be a better reason than that. 

Not all pinstripes are born equal

The first thing to understand about pinstripe suits is that there are a whole suite of different subsets to choose from. From bold stripes to wide chalk stripes to the stock standard pinstripe - one would be forgiven for getting confused by the array of options. 

At the end of the day, deciding on a stripe style ultimately comes down to personal preference and what feels right for you. As a guide, if you’re looking to invest in your first striped suit, a very faint, fine stripe is a good place to start. This style is an easy way to subtly differentiate from the rest of your suiting wardrobe and it isn’t obnoxious in the way that bolder stripes are. To ease yourself in, look at a white stripe on a charcoal or navy base and style it with block coloured accessories. 

If you’re looking for something a little bolder, a wider style stripe might be for you. Evocative of the 80s power suits of yore, this style works best in navy and looks sensational when paired with either a plain white or banker style shirts. Keep accessories plain as this fabric is a statement in its own right. Best suited to tall, slim chaps, wide stripes can make you appear broader so they are best avoided by the vertically challenged. 

For those wanting a half-way point between these styles, there is no going past the chalk stripe. Designed to appear as if drawn with tailor’s chalk, this style is wider than a pin-stripe but not as broad as some bolder styles. Popular in flannel fabrics, this stripe is terrific on a pale grey base during the cooler months and often appears a little more fuzzy, particularly when on softer weaves. 

How to wear a pinstripe suit 

Pulling off a pinstripe suit all comes down to how its styled. Being a pattern that is inextricably linked with Corporate Fat Cats, pinstripes require additional work so as not to seem stuffy. 

The first step is keeping your shirt simple. Opt for a plain white poplin or sateen finish with a French cuff for a polished but pared back aesthetic. Matching the colour of the pinstripes to your shirt adds cohesion to your overall look and will assist in muting an overly loud stripe. It’s a little thing but it makes a world of difference. 

In terms of accessories, keep them minimal. Think about breaking up the vertical lines of your suit with ties and pocket squares in subtle patterns like polka dots. Pairing stripes on stripes, while possible, can appear busy and adds visual bulk to your silhouette. 

Finally, with footwear, stick with plain oxford styles in black or brown. Brogues - while great with a plain suit - can look fussy and over power a pinstripe outfit. Cordwainer of Spain has an enviable selection that are designed to last. 

Wearing a pinstripe suit as separates

For most suits, splitting the jacket and trousers is a great way to give it an extra lease on life. With the pinstripe suit though, it’s preferable to keep them together. The lines, when worn as a full suit, extend the body, slimming the torso and adding height. Pairing the jacket with plain trousers can create a reverse effect, making your outfit appear disjointed and clunky. Instead, focus on the other versatile aspects of your suit, like where it can be worn



When to wear a pinstripe suit 

Not only for the 9-5 grind, a pinstripe suit can be dressed up for more formal occasions - particularly when in a black or charcoal. Think about styling your suit with a silk-grenadine necktie or even a bow tie to elevate the overall feel. Top it off with a pocket square in either a three-point or puffed fold to really go the extra mile. 

If you are wearing a pinstripe suit as a cocktail outfit, changing your business shoes for a tassel or penny loafer can also assist in giving the ensemble a more night time feel. Even explore double-breasted jackets as a way to differentiate from your usual office clobber. 

Alternatively, the pinstripe suit, despite common misconception, can be dressed down too. Relax your look with a plain crew neck tee and white sneakers for an effortless ensemble. This kind of outfit is perfect for events like the polo or even a laid back work drinks. Navy and lighter colours work best in this context - keep your darker hues for work and more formal occasions.