Style + Ask the Edit

Ask the Edit: The Short Story

Do you struggle to find a flattering pair of shorts?  Like many women, today’s question comes from a reader who is still searching for the right pair of summer shorts.

Hi Abra,

My in-laws are taking us on a Caribbean cruise in a few weeks, and I’m at a loss for what to pack.  I overdressed on our last cruise and it seemed to upset some of the extended family members.

You put up a pair of shorts a few weeks ago that you wear.  I can’t find the post.  Can you help me?


I’ve never been on a cruise, so I’m the wrong audience for that part of the question.  But I have the second part covered.

My favorite short is the J.Crew Factory 5″ Chino Short (four colors, sizes 00-16).  You can also find this short at J.Crew in three colors.  For readers who wear sizes bigger than 16, J.Crew offers a chino short in a 7″ length.

I like these shorts because the longer length is flattering and summery.  I’ve never warmed up to the knee-length Bermuda shorts, but I also don’t feel comfortable in the 3″ shorts of my younger years.  I find the shorter inseams can bunch up when you sit and then develop an unsightly, sometimes uncomfortable accordion-wrinkle in the crotch (which has to be one of the worst words ever).

If you’re between sizes, go up.   Shorts a clothing item that is often more flattering when it’s a hair loose.

If you’re on the hunt for something more casual, for hiking or other outdoor activities, I own three pair of these North Face Aphrodite 2.0 shorts.  The shorts come in both 4″ and 6″ inseam lengths.

The material is a durable nylon with a wide, drawstring waistband.  It also has pockets and a small utility pocket on the front.

I wear these shorts hiking.  I wear them to the gym or on when I work out at home.  I sometimes wear them in the car when I travel because they’re comfortable.

As for how to dress for the cruise, hopefully, some of your follow readers can help you suss out a solution.   But I will say, if you  were comfortable, and you felt dressed appropriately, then the opinions of a few extended family members shouldn’t inject doubt into your choices.

I’ve certainly had times when someone’s reaction to my outfit made me wonder whether it was the right choice.  But while it doesn’t hurt to re-examine whether a choice was correct, if you’re doing it because others were upset, remember that their reactions say more about them than it does about you.  This isn’t your office, or an event with a dress code, it’s a cruise vacation.  In that situation, you should wear what makes you feel good.  Unless you’re poolside wearing a tiara and a ballgown, then you might take it down a notch.

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  1. Jessica says:

    Old Navy also has 5″ and 7″ chino type shorts that are often on sale for less than $20. I just bought two pairs for $12 each. Great material that lasts.

    July 29, 2019/Reply
    • Stephanie says:

      I love the Old Navy 5″ shorts. I usually despise shorts but got tired of wearing sundresses on the playground and having the other moms tell me how fancy I looked. The Old Navy shorts fit well, look great, and are inexpensive.

      July 29, 2019/Reply
    • Colleen says:

      I also agree with the Old Navy recommendation. I’ve had these and the J.Crew shorts recommended and the Old Navy shorts look/fit very similar, hold up just as well, and are much less expensive.

      July 29, 2019/Reply
  2. Michelle says:

    The last cruise I went on (which granted was 4 years ago), the younger people actually dressed up more than others.

    I personally think you should wear what you’re most comfortable in though. If you don’t find shorts that you like, you can look at golf skirts. You get SPF protection, pockets, and a lot come with built in stretchy shorts underneath the skirt. You’ll get the more casual look too.

    July 29, 2019/Reply
    • Jill says:

      I have two pairs of skorts from Athleta that I love. Got them in desperation when I couldn’t find regular shorts before a trip. They’re really comfortable and have securely zipped pockets, which I love.

      July 29, 2019/Reply
  3. Ruchita says:

    Every now and then I will try on some shorts that are cute and flattering but then I can’t find any tops. Everything is so long and I can’t get the partial tucked shirt to work for me.

    I wear dresses all the time in the summer. If you like dresses, I think they can work well for a cruise because you can get a range from casual to dressy. For casual, I’m thinking of the jersey swing dresses from Old Navy or the fit & flare dresses from Land’s End.

    July 29, 2019/Reply
  4. Nichole says:

    My DH and I are cruise-travelers. The Caribbean is pretty casual – keep it to shorts and lightweight tops during the day. For dinner, I love a good maxi dress – I often just pack 3 of them and rotate throughout the cruise. Maxi dresses can be casual or elegant, depending on how you accessorize. Every cruise line is a little different regarding their dress code, but a maxi will always fit in! Pack some dressy sandals or wedges, chunky necklaces, and a cute clutch – you’ll be all set!

    July 29, 2019/Reply
    • Lizzie says:

      Totally agree! I just went on a Caribbean / Central America cruise in January and it was pretty casual. You’ll want dresses for dinner–often the dining room has a dress code and won’t allow shorts (for men either). Check with your cruise line, they generally outline what is acceptable. I really like maxi dresses or the Lilly Pulitzer dresses made from tshirt material (not the formal shifts) for Caribbean cruises. You can probably get away with a nice flat sandal for dinner or wedges. Flip flops would be fine during the day. And bring a sweater! I find cruise ships are generally over air conditioned.

      July 30, 2019/Reply
  5. Jamie Patton says:

    Try Kiwi Saint Tropez. I picked up some shorts there on vacation and absolutely loved the fit.

    July 29, 2019/Reply
  6. KaTeL says:

    Amazon Essentials brand has 5” inseam shorts. Many of them are Prime wardrobe eligible – I ordered a wardrobe box with a mix of sizes and colors. Also a fan of skorts – Eddie Bauer, Columbia, Athleta all have fun options.

    As for the extended in-laws comment – people will comment about your level of formality relative to theirs. If you love rocking cute sundresses at the family BBQ or on the family cruise – go for it!

    July 29, 2019/Reply
  7. Rachel says:

    I agree without Abra on short length. In terms of what to wear, it’s hot. Summer dresses are always appropriate in addition to shorts.

    July 29, 2019/Reply
  8. C says:

    1) *Hugs* vacationing with your family sounds… exhausting.
    2) I like Wit & Wisdom’s shorts.
    3) Wear what you want. This is a them-problem, not a you-problem. Unless you’re swanning around boasting about your designer-ware and loudly commenting that your teacher/social worker sibling/cousin could nevvvver afford them.

    July 30, 2019/Reply
  9. Sof says:

    I’ve not gone on a cruise, but I can share my go-to outfit for summer trips to Morocco & central America: loose pants (preferably drawstring or other flexible belting) in fun colors or patterns with a thin fabric & flowy outline. They’re basically classy PJ pants. You can wear them over a swimsuit or just with a plan tank top. I’ve had luck at H&M, Old Navy, & Target.

    July 30, 2019/Reply