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Cruise Clothing: Nautical Stripes & Sailor Style (Updated)

cruise clothing for older women

by Tina Boomerina (Christina Gregoire)

You can never go wrong on a cruise if you are wearing cute nautical stripes or other sailor-inspired clothing. And, almost all women over 40, 50, or 60 look great in these tailored, preppy styles.

Sailor Style for Women

Most nautical clothing is preppy and easy to wear.

read about nautical clothing for women over 50 - cruise wear

Nautical Style Dresses & Sailor Outfit (hipster pinup styles)

However, I need to clarify one point, because not all nautical sailor outfits are designed for preps. Some women (mostly younger women) wear tight, retro-inspired nautical clothing in a Sailor Jerry, pinup girl sort of way... along the lines of, "Hello, Sailor!" ... if you know what I mean.

These rockabilly-ish outfits are usually a bit more punk and tattoo-inspired than what you might want for a cruise. However, if your spirit of adventure encourages you to incorporate some small aspect of this sexy look, I’m not going to stop you.

The red dress (at right) is similar to the type of "sailor" style I'm talking about. Hey, don't get me wrong. This dress is adorable (on someone younger or skinnier than I am). However, most of the time, dresses meant for the tatooed crowd will leave your bazooms spilling out all over, and you might have all the horndogs in your first "port of call" asking you, "How much?"

I just wanted you to know that some sailor styles are a bit different (and tighter) than the usual nautical clothing you're looking for, but if you are younger and can get away with this look, it would be adorable for a cruise.

read about stripes and which are best for you

Cruise Wear for Women Over 50

(This photo shows the kinds of stripes you can wear if you're a little bit older.)

Nautical Sailor Stripes

Can you wear striped tops and dresses even if you aren’t skinny? Well, I think it depends on where the stripes are and how tight the clothing is and how wide the stripes are and a lot of other things. However, if you play with the different styles, you will certainly find some cute outfits that are flattering to your Baby Boomer body.

Personally, I think stripes are cute. However, I have tried on lots of different striped tops and dresses, so I know what kinds of stripes usually look good on me. And, if I can find the right sailor stripes, you can too. I mean, I’m very boho. I’m the least preppy gal you will ever meet, except maybe for Cyndi Lauper. (Well, I never dressed like Ms. Lauper… that name just popped out… I’m actually a bit more like Janis Joplin or Stevie Nicks.) However, it’s difficult to imagine Janis Joplin on a cruise ship. Somehow, the soft hippie look just doesn't look very shipshape at sea. So, I’ve adapted my style for my time at sea.

stripes won't make you look fat - read why

Narrow Stripes (or Breton Tops) Won't Make Women Look Fat

But, back to stripes. Research has shown that horizontal stripes do not make you look fatter. One recent study says that stripes actually make you look taller. It turns out that the most flattering style has narrow black stripes on a white background, ala Breton style. See Resources for more info.

Stripes Are Flattering When Done Right

Striped fashions are all about balance.

For example, I have very broad shoulders, so I must be careful not to accentuate this area, as it is the widest part of my body, and if I'm not careful, I will look short and squat. Most women do not have this problem, but if you are very busty or top heavy, try my approach. I have found that stripes look best on me if I wear a stripey top under a jacket or cardigan. This draws people's attention to the middle of my body (where the stripes are) and gives me a slimmer look. Anyone can do this.

read how to wear stripes

Various Colors & Placement of Stripes

If you are bottom heavy, you will probably look good in outfits that accentuate your top half and your shoulders. So, you'll want to wear striped tops... It’s all about balance. But, that’s just a cliché. You have to take each outfit on a case-by-case basis.  You have to forget your preconceived ideas and learn to SEE yourself in the three-way mirror. Then, you will know the right style when you see it.

Striped Clothing Needs to Fit Properly

As with all clothing, your striped tops and dresses need to fit properly. If your top doesn't hang right, or if you’re always trying to pull something down or up or out or in, the striping will always look off.

This is true with all articles of clothing. And, in general, you should err on the side of wearing something that’s a little too large rather than a little too tight… if only for the sake of being able to breathe… but, also, because the garment will look better on your body.

read about stripes... oh no! ... stripes

Stripes That Go in Different Directions Can Also be Good

Now, I’m not saying that you should wear a pup tent or some baggy mess that looks sloppy on you, but I would rather see you in a garment with a little extra room than something that hugs every curve.  Besides, we don’t want to see your undies… your husband might, but we don’t. (article continues)

Where Do the Stripes Hit You?

As with all the other stuff you buy online, you can’t know if any top or dress (or whatever) will be flattering unless you put it on your body.

look skinny in stripesIt doesn’t matter what a dress looks like on the model, on your neighbor, on your sister, or on your mother. The only thing that’s important is how the dress looks on your boobies, on your tummy, on your tush, on your shoulders, on your thighs, etc.

We all go through this same experience. I know I do. Sometimes, a striped top will draw attention to my chest, which is okay with me. And, other times, a similar-looking top will just make me look "broad" and top heavy, which I hate.

The difference has something to do with the type of fabric, the exact placement of the stripes, the thickness of the stripes, and the contrast between the colors.

But, if I can’t tell you why two similar tops look so different on me, I certainly can't tell you which stripes are best for you. However, I can give you some hints, so keep reading.

Different Types of Stripes

I want to show you some different striped dresses and give you my best guess about each of them. And, because I'm an artist, I'm very good at seeing what is in front of me. I don't think I need a scientist to explain what I see.

read tips for wearing striped dresses

Striped Dresses

Forget what you’ve been told about stripes and just see what you see.

1. Dress number one would look good on someone who is top-heavy (like me) because the wide, evenly spaced stripes add balance to the bottom half of the body.

2. Dress number two would look great on a bottom-heavy woman because the consistent, almost-loud stripes demand that you look at the top half and ignore the rest of the dress; bringing your focus to the lines that curve around the breasts.

3. Dress number three would be great on a small-chested woman because the Breton stripes on the skirt can’t compete with the dark bodice, so your eyes are drawn upwards.

4. Dress number four has uneven striping and your eye is continually moving up and down the dress, unable to focus on any single area of the body.

I think I could wear dress one and dress three. The others might make my large shoulders look too square.  I think pear-shaped women would look good in two, three, and maybe four. Hourglass shapes would probably look good in one or two. And, I think dress number four would look best on women with thick, but less curvy, straight-up-and-down bodies... but it depends on where the different stripes would hit you.

read about nautical clothes accessories

Nautical Striped Accessories

If you can't stand stripes but you really want to look shipshape for your cruise (or your luncheon or your vacation at the shore), you can always wear solid-colored clothing and add one or two nautical-inspired accessories like striped shoes, a striped bag, or a striped scarf.

As you can see, there are tons of different kinds of stripes and different ways to wear stripes. So, if you want to wear sailor striped outfits on a cruise, you can. If you are having a hard time finding stripes that work with your body, and you want a nautical look, there is another alternative to adding stripes with your accessories.

You can wear a top, a jacket, or a dress with edging (or piping), just like the jacket in the main photo. Piping is like a stripe, but it’s a smaller, easier to wear, nautical detail... and of course... a striped hat is always fun when you're on a cruise.

Update From a Boomerina: Jet Metier sent a photo with a note:

read about stripes

Jet Metier Wearing Sassy Nautical Stripes

Tina, I read your post on nautical dressing yesterday and was so influenced that I put together an outfit this morning that was true to your mariner's theme: stripes, green and white in a top that varied in directions and breath, sailor pants buttoned in parallel, old school Adidas tennis shoes banded in black and white, aquatic socks and bracelet and circle earrings veined in phosphorescent colors. (The closest I am coming to water today is a trip to the carwash later.)

My husband came into the my study and hugged me, " I like how you look with all these vertical details. Now this is a look that is picture-worthy."

Tina, you are responsible for spontaneous affection from my husband. And to me that is the best effect of a fashion tutorial.

(Jet, thank you so much for sending a photo. See Jet's hipster article here.)

More Articles for Baby Boomer Women:

Best Swimsuits for Women Over 40, 50 & 60

Women's Travel Cruise Wear Online for Chicks Over 40 or 50

Daytime Cruise Wear for Women With Style

Sexy Plus Size Cruise Wear: Cocktail and Formal Dresses

Photo Credits: Prshots.com and Boomerina Jet.

  • Main Photo: Fifty Plus 2013.
  • Nautical Style Dresses & Sailor Outfit: Eucalyptus 2013.
  • Cruise Wear for Women Over 50: M&CoUK 2015, Wallis 2015.
  • Narrow Stripes Won't Make Women Look Fat: Land's  End 2015, LaRedouteUK 2014, MarksAndSpencerUK 2015.
  • Various Colors & Placement of Stripes: MandCoUK 2015, Land's  End 2015, Long  Tall Sally 2015.
  • Stripes That Go Different Directions Can Also be Good: Betty Barclay 2015, Phase  Eight 2015, Simply Be 2015.
  • Stripes Under Jacket: F & F 2013.
  • Striped Dresses: Apricot, Marks  and Spencer, Crew Clothing (2) 2013.
  • Nautical Striped Accessories: Wallis 2015, DebenhamsUK 2015, Radley 2015, Accessorize 2015.
  • Jet Metier Wearing Sassy Nautical Stripes: Jet Metier.


Coleman, Claire and Kay, Karen. Yes, Stripes Do Make You Look Fat dailymail.co.uk

What do you think of this article? Do you ever wear stripes? Leave a comment at the bottom of the page.

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

Follow Me on Pinterest Follow My Boomer Lifestyle Blog on facebook

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  1. Ruth Harris

    Listen to Tina! She knows what she's talking about. Here's my take:

    Stripes are good! So are navy T's with white pants (linen, if possible). Chunky jewelry if that's your style. No jewelry if that your style (I'm a dedicated minimalist). White espadrilles. Brown leather sandals work, too, maybe purchased in Capri or hand-made by a hippie leather crafter in an off-beat neighborhood. Killer sunglasses. A straw tote. Sun block. Minimal MU. No man-trap designer-label perfume. Maybe a bit of sandalwood (if you can find a good one).

    This approach & the zillions of variations on it will take you everywhere. Everyone will wonder who you are. Plus you get to pack light!

  2. Mike Morris

    Hey Tina,

    Jude wanted me to reach out and say rock on! She is 50 and proud of it! She is designing dresses and clothing that is all about looking good, feeling good and sharing good energy. Colorful and fun ,easy care .. check it out and I would be happy to hook you up if you want to check out first hand..

    Mike 973-879-0028

    PS .Judes my best friend!

  3. Jet

    Tina, I read your post on nautical dressing yesterday and was so influenced that I put together an outfit this morning that was true to your mariner's theme: stripes, green and white in a top that varied in directions and breath, sailor pants buttoned in parallel, old school Adidas tennis shoes banded in black and white, aquatic socks and bracelet and circle earrings veined in phosphorescent colors.

    My husband came into the my study and hugged me.

    " I like how you look with all these vertical details. Now this is a look that is picture-worthy."

    I have enclosed picture just taken in an email to you. (You can post either, if you like.) Thank-you, Tina. You are responsible for spontaneous affection from my husband. And to me that is the best effect of a fashion tutorial.

    • Tina-Boomerina


      I just got back into town and I have a ton of comments to go through, but I'll look for your pic when I can. Thanks so much for sending it. And, I'm sure you looked hot. Spontaneous affection from a husband? Wow. I'm going to copy your outfit and I'll post it here or somewhere and let you know where. We should all copy your outfit!

      That's the best story yet!