Playboy Style: Summer Pool Party Outfit

With summer weather here (in some parts of the country) and with it coming quickly to other parts, it’s time for me to drop some style knowledge on how to dress for pool parties.

While most guys will don some Bermuda style shorts from their local Wal-Mart, I’m aware that my readers are not content with being status quo and are looking for that extra edge.

Below you’ll find a great go-to pool party playboy outfit complete with prices and links to sites (Note: I don’t get commission, it’s just for your easy use) where you can buy the outfit. This outfit is my staple for pool and yacht parties.

Playboy Style: Summer Pool Parties


For most of us, we’ll be shirtless at some point at the pool party. What’s the point of blood, sweat and tears in the gym if we don’t get to show off to the girls? Regardless though, you have to get to the party (driving or cab) and also at some point you might decide to block your skin from the sun, so always bring a shirt.

The light oxford material shirt is classic, lightweight and looks great. Roll the sleeves up slightly and you can keep it unbuttoned, or button it up while leaving the top two buttons open. Go with white, light pink or light blue for the colors. Not only do lighter colors make your skin look tanner, but it’ll keep the rays from being drawn to your shirt. Dark colors attract heat stronger.

Brand: H&M

Price: $29.95

Want to buy it? Go here.



Swim Trunks

Avoid Speedos period and board shorts, unless you’re actually riding waves. These swim trunks are masculine, and somewhat fitted without being too tight, or too baggy. They also have handy back pockets to stash your money clip and phone. The brown color for the shorts matches the oxford in white, light pink or light blue and almost looks like khaki shorts which gives the outfit a classic playboy style. The best part is, they’re made out of swim trunk material so the water sheds as well.

Brand: Diesel

Price: $70.00

Want to buy it? Go here.



If you prefer sandals, skip this one and keep reading. Some cats prefer shoes though and these are great lightweight linen fabric shoes that complete the outfit. You can opt for the classic white, or get bold and get them in a brighter color such as red, or blue.

Brand: TOMS Men’s ‘Classic’

Price: $54

Want to buy it? Go here.



For you gentlemen who’d rather rock sandals, these are classic, look great and are lightweight. Leave the clogs and multi-strap sandals at home. In fact burn em. These ALDO Rozance’s are pricey at $100, but they’re real leather and will last you for years, while maintaining the expensive look.

Brand: ALDO Rozance

Price: $100

Want to buy it? Go here.

NOTE: This is the largest photo I found online to use, but click the link above to see it better.



Protect your eyes from the rays, while you scope the pool for hotties with these classic pair of American Optical Aviators. Not only are they highly rated by users, but they’re much cheaper than Ray Bans and look just as good.

Brand: American Optical Pilot Aviators

Price: $50 (check Amazon for possibly even lower rates)

Want to buy it? Go here.




Don’t forget the final piece, but often the most overlooked aspect of a man’s wardrobe: the watch. This is a great waterproof watch and the rubber band really pulls this outfit together. Sporty, yet slick enough to make you stand out as the playboy you are.

Brand: Lacoste Sport Navigator Automatic Rubber Band Watch

Price: $ (Prices vary based on buying off Ebay, or other shopping sites. Google the exact watch name for the best price)

Want to buy it? (Google the exact watch model. Multiple sites selling it)


On a tight budget?

Take the concept from these pieces and shop around. You can find most of these pieces from even cheaper stores and brands and pair them together to a similar effect. Look at your wardrobe as an investment though. Invest in one good high quality pool party outfit and be ready to go ALL summer long. 


The only thing left is your sunscreen and a sexy bikini-clad model on your arm, but I’m sure with the tools on this site, you’ll do just fine.

Start summer right by making yourself the BEST man you can be. Go here.

Read More: Springwear For Men: The Casual Playboy Outfit

3 Replies to “Playboy Style: Summer Pool Party Outfit”

  1. Hello,

    Thanks for all the tips on the website Christian. Here’s a small contribution back to the community. I thought I’d leave a review of two of the products I purchased based on your recommendations.

    1) Diesel Chino Beach Swim Suit – Bottom Line: I would buy again at a lower price. Overall I think they are overpriced at $70 for what you get. The fit is a bit odd. I wear a 32 waist with suit pants so I bought the same for the swim trunks. I’d recommend going one size down (to a 31) if possible. The fabric is fairly shiny, I thought they would look more khaki like. Also, the diesel site states “Zip/Zipped opening” when in fact the shorts use a velcro (hook and pile) closure. I think this will reduce the life span of the shorts. Additionally the sizing straps on the sides are non-functional, meaning display only like sewn on suit sleeve buttons. The belt loops seem odd for a swim suit. Okay, now for the good points. Lots of pockets…side, back, and a little one in the front. There is a removable mesh liner as well. Various colors are available. As of Friday 24 July 2014, the shorts are on sale for $49.00 and I would buy them again at that price in black.

    2) Aldo Rozance Sandals – Bottom Line I would buy again. Overall these are solid sandals. The sole is non-slip rubber. The build seems high quality. I ordered two pairs in different colors. I fully expect these sandals to last several years. Two down sides to the sandals are that the leather has irritated the bottom of my foot (a hot spot) when wearing them for the first week. This has gradually gotten better. Also, the thong part that goes between your toes is rough and takes several days to break in. These sandals offer virtually no arch support so if thats a requirement you need to shop elsewhere. As of Friday July 24, 2014 they are on sale for between $34.99 and $48.99 depending on the color. These are definitely worth it at that price as they were originally $100, and even at that price would have been a reasonable purchase.

    CAVEAT: As with any item, don’t purchase these items if you cannot truly afford them. These are nice to have things and certainly not requirements for your summertime fun.


Your opinion is welcome...

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s