Free Standard Shipping Orders Over $40.00

About Us - e pili ana iā mākou

For those of you who haven't known us over the years you might ask yourself where did the name come from and just who or what is Smilin’ Jake. 

As to what we are is easy, we’re a little bit of “tropical paradise” on the Eastern Shore of the Chesapeake Bay. We have specialized in Hawaiian, tropical and casual apparel as well as other items you may want to help take you away to that tropical place without leavin’ home.

Now about the name “Smilin’ Jake’s” it was the name of my best friend Jacob Austin Kees Esquire or “Jake”. For you dog lovers, Jake was the happiest Keeshond as you could ever find, and he never went anywhere without his Hawaiian print scarf on and a great big smile for everyone he met, thus a name for the store was born “Smilin’ Jake’s”. 

With surfing & cars being a long-lost passion, I thought maybe I could get back in some small way and not have to move. Let’s face it neither Jimmy nor the Beach Boys are going to show up in Rock Hall, Md and I wasn’t about to hop on the next float plane to Hawaii. So it had been a long time since my last board or show car...... thus the store was born. This brought me back a bit closer to the beach, Buffett and love for Hawaiian shirts. Then Linda & I decided to do the next best thing to owning a street rod again and that was to organize a "Cruise Night" here in Rock Hall, Md. (we probably have more cruiser’s in Hawaiian shirts than anywhere else on the east coast.

In the store you’ll find everything Hawaiian and Tropical. Dresses, tops, aloha shirts, car shirts, swim wear, shoes, music, jewelry, watches, hot sauces and much, much more.

We hope you have some fun, meet some new friends and as we always say you might even find; “Something you want but nothing you need”. 


Jack & Linda

Our brands