Preppy is to the Hamptons as the ocean is to the sand. You can’t just go to the north and south forks of Long Island without looking the part, especially if you find yourself walking along the beach at dusk. I recently went up to Montauk, and after experiencing it all first hand and getting lots of compliments on my outfit, I felt confident enough to give you a few tips on how to successfully pull it off while remaining comfortable, practical, and of course, elegant.





  1. Bring out the preppy guy in you

I have always believed we all have a preppy guy within ourselves, we just need to bring him out and dress him up. But when in doubt, we ought to always remember that less is more. After all, the preppy style is all about being neat, clean-cut, and simple. If you fear you might end up looking basic, you can always incorporate a discreet touch of elegance and sophistication into your outfit with the right fit, the right color scheme, and of course, your demeanor.






2. Choosing light colors and fabrics

Pastel and light colors will be your best allies when going for a preppy look, especially during the warm seasons near the water. You may be barefoot as you walk along the beach, but as long as you have an elegant shirt on, you will always look preppy. For this outfit, I chose to wear a party oxford tucker shirt (Vineyard Vines, $125.00), which is made out of cotton an lycra, the types of fabric that allow you to remain comfortable and fresh with a hidden touch of stretch. This comes in handy when you find yourself running and jumping all over, and playing in the sand.

3. Don’t over accessorize, keep it neat and simple

Because it is so colorful, despite the light tones, it’s not necessary to accessorize this shirt too much, except with maybe a watch. But even if you just wear it with nothing else, this preppy shirt still makes a bold statement, and its colors can definitely stand on their own. I highly recommend leaving the top two buttons open, it gives it a modern, fresh, and young beach look, and it keeps your body cool while you show off your beach tan.






4. Balance the texture while creating a discreet contrast

Taking into consideration the color variation, and the texture of my whale branded shirt, I chose to wear light solid straight fit chinos (Levi’s, $40.00). Trust me, you don’t want to wear one too many colors, otherwise you’ll end up looking like a clown. I always like to balance out the colors I wear with a belt and shoes that are not only similar in color, but also create a contrast throughout my outfit. I recommend wearing brown or cognac, as those colors always stand out amongst lighter shades, but they’re not too bold, and there’s something about them that always looks elegant and preppy.

I chose to wear a cognac belt (Nautical, $40.00) and palling loafers (Aldo, $135.00). By the way, it’s always a good idea to wear no-show socks with this kind of shoes, the less obvious they are, the more they’ll give off the illusion that I’m not wearing any socks at all, and just in case they do show up at some point, I always tend to wear the “nude color” ones, as they’re more discreet. It’s a fresh and modern take that will keep my shoes fresh, clean, and it will keep them from eventually turning sweaty, or even smelly.






5. Have fun and smile!

What I like the most about fashion is wearing clothes that make me feel confident enough to smile. In my opinion, your smile is the most authentic accessory you’ll ever have. Being preppy goes hand in hand with experiencing a luxurious, elegant, and happy lifestyle. Smiling will make you look even preppier. Don’t pretend, though. Just be natural and have fun, Keep fashion fresh, modern, and fun. In other words, stay elegant, and smile… Smile until the end.

What’s your opinion about this outfit? Let me know in the comments section below.

Elegantly yours,

Leo Rivera





One comment on “Simply Preppy At Dusk In The Hamptons
  1. Paul says:

    Love the shirt, bright and colorful. You look at ease on the beach, the choices were great and very summery.

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