A Gaycation - 6 Essential Wardrobe Tips

Hello Sailor Mykonos Greece


- Gay Vacations -

 Now that we've endured our pathetic warm winter and measly two inches of snow, one starts to think about what the summer will bring and what gay destination will lure you for a holiday.

Since we currently reside in the mid-Atlantic region, we find ourselves drawn to the gayest place on earth - Provincetown. We've visited Miami, Ogunquit, Key West, - even Mykonos, but nothing surpasses this little treasure at the tip of the Cape. It's not just a gay street or area in a city or town, but the whole town is bursting with homos and diversity. Heterosexuals are welcomed but realize that they are in the minority and any bad behavior will be dealt with vicious drag queens. No one wants to go there, they will cut a bitch.

When you do choose a destination, you start to consider - what should I wear? In the past when it came to making a Sophie's Choice about my clothes, the solution was just to bring everything I owned to cover all bases.

Maybe we will be invited to a formal ball, or what if we go to a fancy restaurant that requires a tie and jacket? What if we become friendly with some new sailing queens and are invited to a yacht party?

Mary, most likely the reality is - that's not going to happen. Formality is dead, even for the rich. Everybody wants to be cool and comfortable. Unless you show up in your underwear, most nice restaurants are going to let you in, regardless of what you have on. They have about three months in Provincetown to make a year's earnings, they can't afford to turn you away.

When we travel anywhere now, the most I want to schlep around is a carry-on bag. This does whittle down how much you can actually take with you. With this in mind, here is a suggested list of essentials to consider for your week-long stay in the homo haven of your choice.

1. Outer Wear - The further north you go, the cooler it will get at night. Early mornings and night can be pretty chilly, even in August.

A. Rain Coat/Windbreaker - Several summers ago, we spent a week in Provincetown, and it rained practically every day. This would have been a nice thing to have. I would suggest something in a light weight nylon with a hood. Red or Blue always mixes well with summer colors.

B. The classic Jean Jacket always looks good and can be dressed up or down. Look for a lightweight denim, washed but not distressed.

If space is too tight, one of the above would be fine, depending on your destination.

C. Hoodie - A lightweight hoodie is always good to have as a morning layer or for a little warmth on the beach if the wind gets too cool. The French Terry Hoodie we carry is a perfect weight. Our blue one with the white Hello Sailor logo is a great look for summer and layers well.  

2. Tops - ( there are never enough) This is an area where it is easy to take too much.

A. Washed Linen Long Sleeve Shirt - white or blue chambray. This can be worn as a layer or on a cool night out to dinner. I like to wash my linen shirts and put them in the dryer until they are almost dry, take them out and hang them to finish drying. If they are too wrinkled, spray them with a little cool water, and the fabric will relax. I like the soft rumply - but not too messy look. Linen won't wrinkle as much if you don't iron it.

B. Four Tee Shirts - Navy, light gray heather, white and red. Graphic tees can add a little extra zip to your look. Several of our designs will get you noticed and possibly chatted up if you are single or on the down low. Seamen will certainly get their attention :)

C. Nautical Stripe Knit Shirt - For whatever reasons, practically everybody looks good in nautical stripes. You can't go wrong with navy and white. Either a three-quarter sleeve or short sleeve looks sharp on its own, or as a layer.

D. Tank Top - If you are young or still in shape, a tank top is a way to get the boys to the school yard. It's good for a beach cover up - sexy with a speedo, or for riding around on a bicycle. Our new graphic white tank top with the ugly hot sailor, in navy, will look good with anything.

E. Cotton Short Sleeve Button Front Shirt - This is a nice change of pace, and a little dressier if you go to a place that requires shoes. You could have fun with a floral pattern or check. This could also be layered over the tank top.

3. Bottoms ( you know who you are) These can be worn multiple times so you don't need a lot.

A. Jeans or Cotton Pants - 2 pair- I like to have something in dark denim for a dressier look. White or natural for a crisp casual look. Long pants can add a little warmth on cool evenings.

B. Shorts - 3 pair - Denim, white, khaki, or a color of your choice (red, pink, etc.) I like a jean short. They look good on most body types and go with anything. Shorts should hit just above the knee or can be a little shorter. If you have great gams, why not excite the boys with short shorts. For the rest of us, the cut should be trim and not look like you are wearing a skort. It's a good idea to have one pair of dressier shorts.

4. Bathing Suit - God knows why, but most everybody looks good in a speedo, from the beariest to the twinkiest twink. For the rest of us who really shouldn't go there, a short style swim trunk is the best way to go. Bathing suits should be at least mid thy or higher and trim cut. If your bathing suit floats around your waist when you are standing waist high in water, it's most likely your bathing costume is a man repellent, and far from sexy. This is especially where you don't want to dress like a straight man :)

5. Footwear and Belts - This is always the true Sophie's Choice, but in reality, the simplest. All you need is one pair of dressier sneakers, one pair of sports sandals, and one pair of leather sandals. You can bring or wear running shoes if you are one of those who insists on wasting time keeping in shape.

I have a navy braided elastic belt that I wear with everything all summer. It looks good with leather shoes, sandals or sneakers.

6. Basics - Since you probably don't plan on doing laundry while you are on your gaycation, take clean underwear for each day. I usually pack one extra in case of emergency. So far I haven't had to cash in the contingency pair, but it's best not to tempt fate.

A nice pair of knit shorts and an over sized tee shirt are always good to have around for lounging or napping.

I usually bring two or three pairs of sneaker socks, just in case you have to put your sneakers to good use and not ruin them with your sweaty feet. We tend to wear sports sandals most of the time. 

If you have room, it's always nice to have a light weight robe.

The most important thing to remember is that you're on holiday and to hell with trying to impress other queens. You should look good and fashionable, but you don't need to be Penny Peacock. She probably rented a house for the summer and brought every stitch of drag she owns.

I wish you fair winds and smooth sailing!

 Don Bostick

Creative Director - Hello Sailor TMH


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