Add Flair with a Square
I never knew I had so much to say about pocket squares until Real Simple asked me to talk about them. The bottom line? Buy some, you monster!
Below is a quick Q&A about the most-commonly asked pocket square questions (yes there is such a thing), some photos of me rockin' squares, and some that I think you should buy. Voila!
When do you like to wear pocket squares? Do they work for any occasion? Are certain fabrics dressier than others?
Pocket squares are more versatile than they get credit for. Of course I wear them in the pocket of a blazer – everything from an unstructured casual blazer to your traditional country club-appropriate navy number – but I also like to tuck them into the pockets of overcoats and even a shirt pocket if you’re feeling particularly 70s Hugh Hefner. And you should feel 70s Hugh Hefner every once in a while.
All pocket squares are not created equal, some are definitely dressier than others. In general, I think the smoother the fabric (like silk) the dressier it is. Wool is great for fall, and linen is perfect for summer.
How do you choose which pocket square to wear? Do you like to match them to a certain part of your outfit?
It probably sounds like I’m being paid by the Pocket Square Lobby in an attempt to drive up sales, but the truth is that you only need a few to choose from. A navy and red Hermes pocket square I have goes with about 80% of my wardrobe, a burgundy Gucci one goes with the other 20%; I think if I added a solid grey option I’d be set for life.
Don’t worry too much about “matching.” The mot du jour should be “coordinating.” The pocket square should go with the rest of your outfit without matching exactly – matching to me means sets of Donald Trump Collection tie/pocket square/cuff links packaged in plastic-fronted gift boxes. Wearing winter wool trousers? Add a heavier-weight square. Rocking head-to-toe navy? Maybe red will stand out in just the right way. The right combination is like porn: you’ll know it when you see it.
Why do you like incorporating pocket squares into your outfit? Do they up the style ante? Do they "finish" a look?
They add another bit of personality to your outfit. New York in the winter is a sea of navy, black, and grey outerwear – so I like to punch it up a little with a pocket square. If you do it right, it’s a style move that’ll set you apart from people to just throw clothes on the morning. They show you care.
Finally convinced you need a square or three? Below is a gallery of my favorites right now: