Effortless Style for End of Summer

What is effortless style?

Go to Google Images and type in “JFK at Hyannis Port.”

No really. I’ll wait. 

What did you see? You saw John and Bobby walking down the beach in blazers, John and Jackie sailing in polos, the pre-presidency Kennedy siblings in swimming gear, John rocking the Wayfarers, attending an outdoor wedding, and another where he’s wearing a long-sleeved cotton shirt and shorts – sockless in loafers – holding a golf club. It’s as if Webster’s called and needed a pictorial definition of the word effortless

As late summer tiptoes into autumn, some of us move from picnic season to tailgate time, or from cookouts to clambakes.  Even though these are all informal events, we don’t want to dress as we would if we were going to clean out our garage on a Saturday, right?

So what do we need? Options.

Long- and short-sleeved shirts. Thin cotton sweaters that button up. Cotton shirts that button down, layer, and play nice with a jacket and tie.  Solutions that kick it poolside and ride around with the top down. If you do it right, a mid-sized duffle and two pairs of shoes will take you from the beach bachelor party to the ceremony and right on to the reception with the right tweaks. 

Bucks Oxfords in Chestnut

Fast Shoes in Tan Waxhide

Fast Shoes in White

Highlander Shoes in Brown Pebble Grain

You’ll note that the subject of this blog post effortless style. Both words are important.  The person pushing a shopping cart at the supermarket with the word PINK across her rear end is showing effortlessness. Is that really what you’re shooting for?  It’s the word style (notice I do not use the word fashion here) that’s key. It’s really about being comfortable, feeling your best, and looking well put-together.

We can’t all look like young JFK at Hyannis Port, but we can all dress for the event, our body types, and the weather in a way that’s comfortable and contemporary.

Photographer Jason Prziborowski wearing Uptown Mavericks in Whiskey


Brian P. Cleary is an American humorist, poet, United States patent holder, inventor and author. The bow-tie wearing children’s author is best known for his books that explore grammar in humorous ways written for grade-school children. To learn more about Brian and to see his work, click here