I need help. Honestly, I’ve needed help for a long time, I was just too scared to admit it. But here I am, admitting to the world that I’m addicted to cargo shorts and flip flops. This was not a problem ten or fifteen years ago when such an ensemble was acceptible attire for any time and place for someone of my age and sensibilities. But not only are these different times, but I am different as well, aged and, hopefully to some degree, more distinguished. Thus it is time for me to shed the utility of extraneous pockets and thonged footwear and transition to something more befitting of someone of my seasoned age.

Typically when it’s time to add some new life to my closet, I turn to end of season sales or tried and true traditional wear. This time, I turned to the close friend who pointed out my cargo-pocket addiction to provide some suggestions for summer footwear. The specific charge: send me a few notes on something I can wear casually but can also transition to a nicer setting should the need arise. Take a look at what he sent and then keep reading to discover what I settled on.

Chacos
“The outdoorsman’s companion.”

My wife loves her Chacos but I never really considered a pair for myself. Maybe that’s because I gave up on strap-in sandals after a long love affair with Reef convertible sandals in my late teens / early twenties. These probably aren’t on the shortlist for me, but they’re a great option for casual wear or short hikes on weekend trips.

Sebago
“Every man should own some boat shoes and I choose to go against the grain.”

I don’t know if I agree that every man should own boat shoes, but I’m starting to warm up to the idea. In fact, I’m warming up to it so much that I decided to take the plunge and grap a pair of these Sebagos. It’ll be interesting to see if this will be a style that sticks for me, but I’m at least excited about the endless possibilities that come along with being set adrift on the open waters.

Brooks Chariot
“A nice kick-around shoe for those more active days”

A couple of years ago I picked up a pair of New Balance Minimus shoes on clearance and they are my go-to pair for errands or weekend events that I know will involve lots of walking or standing around. The Brooks Chariot are a great option for similar situations and they’ll provide a little more comfort than the Minimus.

Sanuk Casa Barco
“Casual shoe that could be worn to dress up an evening out.”

I haven’t owned a pair of canvas shoes since my Keds in elementary school, so this would certainly be a leap for me. I prefer the nicer look of the Sebagos, so those win out for me, but this also looks like a nice and easy casual option for those breezy weekend errands.

Sanuk Beer Cozy Flop
“They come in many styles, but I think the Beer Cozy is one comfortable flop.”

These are a little out of context because my original charge asked for something other than flip-flops. I’m including them anyway because I actually decided to grab a pair. Even though I’m trying to rely less on flip-flops, my 2 year old (maybe 3?) are on their last leg and I’ve decided that maybe it’s time for a break in my 10+ year relationship with Reef flops. These Sanuk Beer Cozy Flops sound, well, very cozy and they’re not so astronomically priced that I would feel bad ditching them mid-summer to return to my old standby.

There you have it, a plethora of options to get you through a summer full of beach trips, boat outings, and outdoor music festivals.