As with most articles of clothing there is a time and place for everything. Unfortunately (I maintain an extensive collection) the fitted hat is neither appropriate or acceptable with every outfit. For that reason as with most accessories you have to branch out. Now don’t be scared you can rep your favorite team at the local BBQ or casual event but not with a three piece suit or at most NYC nightlife venues.¬† So below are a few other choices that not only will keep you on point but also easily accessible & venue appropriate.

Driving Cap

This ever-popular, classic men’s cap is usually styled in wool and acrylic with a nylon lining. Snap-up visor and elastic back for a perfect fit. Great for being out on the town or out in country, it will provide years of warmth and comfort and goes well with business attire or casual wear.

Driving Cap


A fedora is a felt hat most commonly worn by men. The term is usually generic, describing any men’s hat that does not already have another name; a few fedoras have names of their own, including the trilby or homburg. The hat is typically creased lengthwise down the crown and “pinched” in the front on both sides. The most notable after the fitted and great for tropical destinations as they do come in straw as well.



A trilby hat is a type of fedora. The trilby was once viewed as the rich man’s favored hat. It is also sometimes described as a “crumpled” fedora. The trilby has a shorter brim which is angled down at the front and slightly turned up at the back.¬† Traditionally it is made from rabbit hair felt, but is usually made from other materials, such as tweed, straw, wool and wool/nylon blends. Can be seen at the races or music icons such as Ne-Yo.



The Bowler hat is the first hat credited for being mass produced and priced to meet everyone’s budget, because of this the Derby Hats were worn by virtually every class of society. The derby hat comes in many different styles from the low-crown to the stingy brim. Usually a hat for coachmen but obviously the style translates to other walks of life.


Hopefully this helps you advance your style a little bit. If not at least you what the options are when they say no fitted allowed.

So gentleman, the unofficial start to the summer is upon us which also means since the weather changes so does your wardrobe. But what must remain is the mainstay of style. So whether you have packed up to head somewhere tropical and breezy like Miami, Cancun, Myrtle Beach,D.R. style incorporates  some board shorts or speedo.

In NYC if it doesn’t rain your going to BBQ hop like a rolling stone with no home here are some outfit ideas to keep the eyes on you and not the grill.

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Camo shorts have been big for a couple of years now so why fix what isn’t broken. Pair with your favorite tee since they are the ultimate utility piece to your summer wardrobe. Of course the fitted cap / Jordan combo is a staple of mine so head into the closet and pull out your favorite pair.

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Want to turn it up a bit, ditch the Jordans & fitted pull out your favorite pair of slim jeans and pair with a classic polo. For the shoe game a nice casual sneaker is the move. Some like boat shoes, I personally like a clean shoe which feature different materials like tweed or tumbled leather. Its a classic look updated for the times we are in.

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Want to impress? Get well dressed in the lighter neutral hued pants. Usually dressed up with a blazer & tie or with a polished sweater but for the weather we expect dress them down with a denim or chambray short sleeve shirt. A nice pair of oxfords from designers like Cole Haan complete the look and keep you comfortable. Its the perfect finishing touch.

Here’s a few options but obviously there’s many more.. I’m only one man.