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Build A Wardrobe that Goes From Day to Night

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The true spirit of a Madda Fella runs deep, and like a good rum, he gets better with age. Your clothing should be as versatile as your spirit of adventure. We understand the need for seamless transitions from sun-soaked days to enchanting moonlit evenings. We're here to make sure your wardrobe keeps up with you and share some tips on how to build a wardrobe that will transition from daytime to nighttime with ease, and serve you wherever the day (or night) takes you. So, sit back, relax, and let our Madda Fella team be your style compass.

Start with a Solid Foundation. Embrace the day relaxed and ready. Linen is a staple for sultry tropical days and nights, and a breathable pair of linen bottoms are the perfect foundation for a casual yet put-together look. Plus, linen is meant to have a natural texture, so that lived-in look is perfectly designed for the adventurous soul.

When choosing shorts, opt for a pair with a longer inseam. 100% Irish linen, like the fabric used for our Truman Shorts, is soft, airy and breathable —  a necessity for those hot days. The vintage pre-wash and tailored cut mean you don’t have to sacrifice comfort for style.


Swap in your shorts for a pair of linen pants for the epitome of laid-back Caribbean style. Versatile and as comfortable as your favorite lounge wear, linen pants like our Linen Drawstring Pants can be dressed up or down and still lend an air of elegance to any ensemble. Pair them with a linen top and even a blazer for a night on the town. Whether you prefer to roll your linen pants or wear them down, we’re confident they’ll be your new go-to.

Be Cool & Confident. Level up without heating up by choosing shirts made from breathable, natural fabric. Shirts made from fabrics like linen and cotton are essential for balmy Caribbean days. Choose shirts with a finished hem to lend some polish to a casual, untucked look.

A long sleeve button-down can add sophistication to a tailored pair of shorts, but it doesn’t mean you have to suffer the heat. Our crisp, seersucker 100% Cotton Dobby Shirt will keep you looking sharp while protecting you from that Caribbean sun by day. And it transitions seamlessly to a cool evening breeze. Flip up the cuffs for a relaxed look that shows off the contrast fabric lining and a touch of vibrant color. 


Mix up your wardrobe with a classic short sleeve button down shirt. Try a camp shirt style with a bold pattern, or go for a simple and add texture for interest. The unique alforzas (pleats) and embroidered flamingos on our Guayabera Shirt adds subtle panache to an outfit. Breezy and effortlessly stylish, this classic and functional style has a storied history. It’s a quintessential piece that combines island charm with a touch of swagger. The lightweight linen fabric keeps you cool, and pairs beautifully with any linen bottoms for a laid-back yet polished look that effortlessly transitions from boat to bar.

Layer it up. Don’t forget a sweater for an evening enjoying that cool ocean breeze. A knit sweater in a light cotton is perfect for those nights with just a hint of chill in the air. Try the Madda Fella Balao Crew Neck Sweater in Ocean Blue for a perfect neutral. The comfortable relaxed cut makes it just right for layering over a collared shirt or even a Henley.

Now that you’ve created a minimal wardrobe with maximal versatility, don’t forget the perfect duffle to get you there in style. The masterfully crafted Key West Weekender Duffle in full grain leather will weather well and get better with age.


There you have it — the ultimate guide to effortless style. With this carefully curated collection, transitioning your look from day to night has never been so easy. Whether you're taking in some history, biking around town, or enjoying drinks and Conch Fritters by moonlight, you'll always be dressed for the extraordinary.

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