What to wear? Men should use the same general advice I give to women…keep it classic! Save the trendy for…never. Men are able to pull off a perfectly polished look with a few key pieces. First and foremost, know your audience, venue, etc.
A day at the beach: Unless you are European or a chiseled specimen of man, skip the speedo. Board shorts come in different lengths and look great on most men. Be sure your suit / shorts fit properly…too tight and you get a muffin top…too loose and you risk a wardrobe malfunction. A classic white tee pairs well with board shorts and / or a muscle tank-vulgarly referred to as “wife beaters” (poolside or beach side are the only times these should be worn IMO).
Poolside at your resort: Same as above…however, if you are not comfortable wearing a white tee (messy Marvin), wear a tee free of any offensive language and / or gestures.
Daytime Resort Wear: Many upscale resorts have a dress code (Ritz-Carlton, the W, the Four Seasons, etc.) but even if they don’t, a few simple pieces will keep you presentable at lunch and / or cocktails. A great pair of luxurious dress shorts paired with a short sleeve button down shirt always looks classy. Invest in a white linen shirt that can go from day to night easily. If a Polo style shirt is more to your liking, invest in a nice shirt in a breathable fabric without designs…this too can go from day to night. If you are NOT staying at an upscale resort with a dress code, feel free to substitute a nice pair of chino shorts in either black or khaki…both are versatile with a breathable fabric. If you are going to wear a pair of madras shorts (I LOVE these-the man won’t wear them), pair them with a solid shirt (preferably a linen button down or thin tee) in a complimenting color.
Nighttime Resort Wear: Many of the daytime pieces can be worn at night. However, now you can add a pair of linen pants, light weight slacks or a nice pair of dark denim jeans.
Footwear recommendations: Ugh! Nobody wants to wear tennis shoes to the beach and they instantly downgrade your outfit. Invest in a great pair of flip flops and a great pair of leather sandals. Also, you can complete most outfits with a nice pair of top-siders (like Sperry).
Cobian flip flops claim to be the most comfortable flip flops. The man loves them! They look nice and can often go from day to night. More importantly, you can walk in them forever! ($30-$75)
If you have chosen a button down style shirt (like a Tommy Bahama shirt), I recommend wearing a light weight tee underneath…this not only keeps you cool, it also protects the fabric from perspiration and sunscreen. If you are wearing a white tee and / or linen top, be sure it is crisp (not dingy) and clean (without stains).
Headgear: A Panama hat is appropriate for the beach or poolside. You can also wear a straw fedora-style hat for daytime and zero hats in the evening.
Sunglasses: Invest in a pair of high quality sunglasses…the key is not the darkness of the lens but the UVA / UVB protection.