The 5 Pocket Squares Every Well Dressed Guy Should Own

The Author, Tim S., is a government relations professional in Washington, DC. He has two boys in preschool and a wife who lovingly tolerates his enthusiasm for the Dallas Cowboys and his style excursions. Except when he speculates that his four-year-old might be nearing the age where he can mix in a pocket square.

I love pocket squares. I love knowing that the ancient Egyptians and Marie Antoinette play key roles in pocket square history. If George Costanza’s fantasy indulgence was to be ensconced in velvet, mine is to lounge around in a tracksuit made of stitched together pocket squares. But you don’t have to go overboard: if you wear anything with a breast pocket more than three times a month, you can multiply those outfits’ versatility and class for less (and often much, much less) than $75. Here are five staples to strongly consider adding to your rotation.

 

Square #1: The Crisp White Linen

The Picks:

• Kent Wang White Linen – $20
• The Tie Bar White Linen – $10
• Sid Mashburn White Linen Hem Stitched – $25

I reach for this one more often than any of my more elaborate options. Timeless enough for Connery and Craig, and the one you see most often on modern gurus like Nick Wooster and Sid Mashburn. Fold it nonchalantly into your blazer pocket, or neatly press the edges and wear it with black tie. Spend a little more if you can afford to; like dark denim jeans, there’s a big quality bump when you go from the bargain bin to the intermediate price range.

 

Square #2: The Tipped Square

The Picks:

• The Tie Bar, White Linen with Navy Border – $11.99
• Kent Wang, White Linen with Medium Blue Border – $25
• J Crew, Cream Wool with Red Border – $29.95 ($39.50)

Your foundational squares should be versatile, and this one will pair with 90 percent of your jacket, shirt, and tie combinations. I prefer something with a blue or red border; for the same reason those shades tend to be the base colors in your most versatile ties. You’re going for a subtle effect here, so this one should be folded and tucked so that no more than about half an inch is showing.

 

Square #3. Repeating Pattern/Print

The Picks:

• The Tie Bar, Red Wool Paisley – $10
• Gagliardi, Cream and Navy Wool Floral – $16
• Suit Supply, Blue with Red, Gold, and Green Medallions in Wool – $49

If you are wearing a tie, one of the easiest tie-to-square matching rules is to pair a minor color in your pocket square with the major color of your tie. Squares with a symmetrical, multi-colored pattern yield the best matches. Pure silk squares are unduly shiny at lower price points, so look for something that includes at least some wool, cotton, or linen. Use some variation of a bunched fold here that shows a little more fabric.

 

Square #4: The Bold Standout

The Picks:

• Gagliardi, Wool Paisley in Sky and Yellow or Red and Yellow – $16
• The Tie Bar, Cotton Gingham in Sky or Royal Blue – $10
• Kent Wang, Lindisfarne Gospels in Silk – $45

If your first three squares are understated elegance, this is a more fashion-forward choice that people will notice. Best worn tieless or with a conservative tie and shirt pattern. Opt for brighter shades (oranges, yellows, and blues are versatile) and bolder ginghams, plaids, and paisleys. Work up to this kind of square a little; if this is the first one people ever see you wear it will look like you are trying too hard.

 

Square Number 5: The Gifted Splurge

The Picks:

• Drake’s, Silk Unicorn in Blue/Green or Navy/Orange – $60
• Drake’s, Cotton/Silk Multiple Medallion in Blue – $63
• Armstrong & Wilson in Brown, Navy, and Orange – $65
• J. Crew Italian Linen Pocket Square (above, sold out)

A gift-receiving occasion is a terrible thing to waste. Whether a late Father’s Day gift certificate or a Christmas stocking stuffer, you’re going to get something in the $50-75 range, so why not drop a hint and get what you want? This is the range in which pricier silk prints are worth the money, and where higher end materials and printing processes really do look better.