How To Wear Pinstripe Suits Just Like The Best (Straightforward Tips)

Ed Ruiz

11 December 2017

Pinstripe suits send a very strong level of authority and power.

So much that they might as well be considered the embodiment of power dressing.

Understandably, for this very same reason, many men will feel intimidaded from ever attempting to step into the wonderful world of the pinstripe.

Sounds like you could be part of that group of men?

If you came here from a search engine asking “how to wear a pinstripe suit?” then it’s likely that you are.

But fear not my friend, in this post we will unravel the secrets of the pinstripe pattern and get you rocking the pinstripe suit with confidence in no time.

How to Wear a Pinstripe Suit

Pinstripe Suits Mean Power

If I were to ask anyone what comes to mind when you see a man in a pinstripe suit, I bet a large percentage of responses would be “power”.

We have recently talked extensively about how clothes have an amazing power to send messages and influence our behavior and even how certain clothes can give us a much deserved boost of confidence.

So it should come as no surprise that a pinstripe suit is not the exception to the rule.

And the message it sends is a very authoritative one.

A message of power, success and even a bit of arrogance (the level of arrogance can vary a lot depending on the personality of who is wearing the suit).

If you really want to excel at wearing pinstripe suits, you have to know what you are dealing with and use pinstripe’s fundamental traits to your advantage.

Realize that that the pinstripe suit demands you to accept the fact that you will indeed be wearing a powerful and elegant look.

Don’t make the stupid mistake of trying to dress it down.

If there is one thing I know is that you just can’t go against nature and the very nature of the pinstripe suit is to be dressed up.

Embrace this fact and don’t even try to come up with a clever way to turn it into a casual garment or you will end up looking like the fool who attempted to dress down the pinstripe suit.

You don’t want to be that guy.

Key takeaway here: The pinstripe suit wants you to dress him up. Obey him!

Plain Shirts Are The Perfect Companion To Pinstripe Suits

The power of the pinstripe suit calls for elegance and cleanliness from other pieces of the outfit, specially from the shirt.

A plain white shirt, with its remarkable class and elegance, is the obvious (and best) choice.

It gives the pinstripe pattern enough freedom to deliver its punch effectively without ever looking like there is too much going on.

In fact, I would as far as to claim, any loud patterns on a dress shirt paired with a pinstripe suit will simply ruin the look.

If you will wear any patterns on your shirt, go for very, I mean veeeeeery subtle patterns, almost non-perceivable from a certain distance.

Technically speaking, a spiffy bengal stripe will work, but you’ll be in dangerous territory right there, so you may want to avoid taking unnecessary risks.

Don’t overthink it. A plain dress shirt -ideally white- is easily the best choice to wear with your pinstripe suit.

Dan (@thebigsartorialist) is an expert at balancing the elegance and power of the pinstripe with fun, personal touches.

Neckwear And Accessories Must Follow Suit And Be Dominant

Now this is rather a personal preference that I’m talking about.

Sure, wearing a discreet tie can be a great choice, but there is something I truly love about an authoritative tie that pairs very nicely with a pinstripe suit.

I am not talking about loud, flashy or flamboyant.

I mean powerful.

Completely different concepts, if you think about it.

To give you a clear idea, think of a graceful red tie or an iconic regimental stripe.

A tie that makes an energetic statement and pushes forward the potent look you should be going for with the pinstripe.

Same applies for other accessories like your watch, suspenders/belts and even cufflinks.

Read also: Suspenders vs Belts: Which One Should You Wear With A Suit?

Favor metal watches over leather ones. Metal cufflinks over… well, any other alternative.

Are you following me? Powerful elegance is what you should be aiming for.

There is one exception to this advice, though. That would be the pocket square.

A loud design on a pocket square paired with a pinstripe suit can end up being disastrous (trust me, I tried and failed once).

When it comes to pocket squares with pinstripe suits, you’re better off going with something similar in color and tone to the shirt (hint: plain white with a presidential fold will always do the trick).

One last waning: keep it powerful, but never crazy, simplicity is always key.

Pinstripe Suits Call For Elegant Footwear

The last piece of the puzzle.


Read also: How To Match Your Shoes To Your Suits (Ultimate Guide)

No other type of dress shoe will complement your pinstripe suit like an elegant pair of lace-up shoes.

Loafers? No, thank you.

Monk straps? Hmmm… could be an honorable contender, but ultimately falls short.

Remember I am trying to give you a simple and effective recipe you can always use to look your absolute best in your pinstripe suit, so I won’t recommend anything but the most appropriate option.

The lace-up shoe wins. Hands down.

But you ask: which of the available lace-up shoes would be the absolute best choice?

Derbys? Oxfords? Wholecuts?

In my opinion, all these options would make good choices and you only have one of these variations in your wardrobe, any will do.

If you are one of the lucky ones that have options at your disposal, then here’s a quick list that could help you decide.

From best to worst:

  • Oxfords: Simply the best companion in footwear to the pinstripe suit. Boasts just the right amount of elegance that is required.
  • Wholecuts: Technically a variation of the Oxford shoe, which makes it another very good option, except it has an air of modernity that may underplay the timeless elegance of the pinstripe suit.
  • Derbys: Last in this list, but still a good option. It just lacks elegance when compared to the other two and more appropriate options.

In short, and if you don’t want to feel too bothered, any pair of clean and simple lace-up shoes are perfectly acceptable choices.

On a related topic. Make sure your socks will match your suit pants.

Lace-up dress shoes are the best choice to wear with your pinstripe suits. (img src)

Stop Feeling Unworthy And Embrace The Power

It is understandable that you may feel intimidated by wearing a pinstripe suit.

A pinstripe suit will demand powerful elegance from us as the wearers.

And really, who are we to say no and go against its basic needs?

Follow the simple guidelines I shared with you here and you will be rocking the pinstripe suits like the best.

In summary:

  • Clean, crisp, simple dress shirt (white is a great choice).
  • Elegant and powerful accessories.
  • Uncomplicated pocket square (similar color/tone to shirt).
  • Clean and polished lace-up shoes.

There you have it, gentlemen.

Did I miss something or do you have any specific question about how to wear your pinstripe suits?

Ask away and I will try to give you my best answer.



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