How I Wear My: Vacation or Resort Look

How I Wear My: Vacation or Resort Look

Welcome to How I Wear My: Vacation or Resort Look, the 59th post in the How I Wear My series!

Can you believe summer is nearly here? With the official start of the season only days away, Jill and I thought it was a great time to focus this month’s “How I Wear My” on vacation or resort looks.

Jill of Everything Just So, my How I Wear My partner, starts us off with her vacation look and says:

“Any vacation plans I have almost always include a trip to a museum so I like to pack pieces that are casual but still look good enough for a day in a more formal setting. I’m wearing a striped top from Target, Old Navy white jeans, a Duchessa Jewels necklace, and carrying my Elizabeth Taylor tote.”

How I Wear My Vacation Look Jill

Dawn Lucy of Fashion Should Be Fun tells us:

“This is a tunic that I usually wear with leggings, but I decided to give it a spin as a vacation look!”

how i wear my vacation resort look dawn lucy

Susan of Une Femme d’un Certain Age has this to say about her vacation look:

“I’ll be packing this outfit for our upcoming vacation to London, Normandy and Paris. I love how this scarf cape adds both color and drama to simple black separates.”

How I Wear My Vacation Look Susan

Reva of It’s all Fine. Whatever tickles the fancy. says:

“The Husband and I stayed with friends in Cayucos this past Memorial Day weekend and spent one of the days wine tasting in Paso Robles.  We’ve been to the area several times in that last few years and it was nice to see all the greenery of the vineyards.  My outfit is quite simple; a breezy skirt, a sleeveless blouse, a denim jacket to throw on later in the day, and fashion sneakers for comfort while walking around all day.”

How I Wear My Vacation Look Reva

Shuchita of Passion Unbridled is a first-time participant in the How I Wear My series and tells us:

“I wore this outfit while exploring Abu Dhabi, United Arab Emirates. This outfit exemplifies how I dress for travel within cities across the world – I start with a lightweight modest shirtdress (this one is from LOFT), add a colorful scarf (bought online from Peach Couture) for visual interest and as a second layer for chilly evenings or for covering my head (for visiting religious places in the Middle East and India), sturdy flats (the loafers are from Coach) and a large neutral colored bag (Adrienne Vittadini). The bag also contains a pair of black leggings which I throw on if visiting religious places or if the weather turns cooler.”

How I Wear My Vacation Look Shuchita

Linda of A Labour of Life says this about her vacation look:

“My one staple on vacation seems to be a fedora of any kind and thanks to Carnival Cruise Ships, I have several in lots of different colours.  My fav is my white fedora, especially when paired with a striped J. Crew Dress/Cover-up and some fun Converse kicks.  It’s cruise ship worthy and great for transitioning into local sight-seeing.”

How I Wear My Vacation Look Linda

Beth of Tall Fashion Adventures tells us:

“As an expat in Europe, I am buying up every opportunity to travel and putting together travel outfits is half of the fun. I find that skirts are a very versatile option when on a trip because they can be dressed down for day and dressed up for night. On last month’s visit to the stunning wine region of Piedmont in Northern Italy, I wore a blue sheer silk blouse from the ethical tall fashion line Marge Clothing, my special Tiffany & Co. pearls and a black/white graphic skirt for a lovely dinner in the vineyards.”

how i wear my vacation resort look

Catherine of Not Dressed As Lamb says:

“I wore my pink and white striped vintage DVF jumpsuit in Santorini last year: A little more subtle than all pink, I hadn’t worn this jumpsuit in the UK all summer (blame the weather) and it suited the beautiful scenery to a “T”. I bought the gorgeous red leather sandals over there and the fringed white crossbody bag was a stylish but practical holiday accessory – with this outfit white fringing looked so much better than black would have done.”

how i wear my vacation resort look

Nancy of Nancy’s Fashion Style tells us:

“Here’s a picture from my vacation in England last week. This polka dot dress has been a favorite for years. It’s very wearable with a legging. During the day I wear it with sneakers and at night with red flats.”

how i wear my vacation resort look

Shelbee of Shelbee on the Edge tells us

“This white gauzy fluttersleeve dress is perfect for the beach as a cover up or for lunch on the boardwalk.  It is super lightweight and airy and makes enough statement with its dramatic flutter sleeves that you don’t even need jewelry if you don’t want to be bothered!  I added some sparkly black sandals and done!  This dress is from Old Navy and shoes are from Payless.”

How I Wear My Vacation Look Shelbee

Dale of Savvy Spice tells us about her vacation outfit:

“One of my favorite resort style looks is a maxi dress. I think it’s the perfect carefree style for a dinner out on a tropical vacation.”


How I Wear My Vacation Look Dale

Christine of Early Indigo, who is also joining us for the first time, tells us:

“Well….I may not be going to a resort and I may be having a ‘STAY-cation’, but that doesn’t mean I can’t have a DIY spa day at home! I am wearing a Chambray Linen/Cotton Kimono-Style Robe which I designed and just started selling in my Etsy shop: Early Indigo.  I refer to it as a modern take on the classic kimono. The robes are trimmed with fabric sourced from Japan, have an inset belt and 3/4 length sleeves.  The cotton/linen content makes the robes breathable, absorbent and easy to care for….simple, yet elegant! I am offering 20% off with code: IndigoJune.”

How I Wear My Vacation Look Christine

Alice of Happiness at Mid-Life tells us this about her vacation look:

“My vacation looks always have a hat, sunglasses and comfy clothes.  This fun camisole from Loft is comfy and so perfect for vacation wear.”

how i wear my vacation resort look

Ana of Mrs. American Made tells us:

“What perfect idea for the post this month as school ends and summer begins so do vacations. We are lucky to be heading to Hawaii again in June. My outfit is so simple and breezy. It is a navy blue drawstring waist dress #MadeinUSA by Hard Tail purchased on Kauai one summer. I bring it back with me every year because I love to wear it on the beach or out to dinner with sandals – like I wore it here to my birthday dinner! Accessorized with just a pair of crystal earrings and hair pulled back.”

how i wear my vacation resort look

Greetje of No Fear of Fashion says:

“The breezy silk blue/white/yellow top is perfect for hot weather. Which is why I am wearing skinny capris with them. If I have to walk for miles, I change my heels for ballerinas.”

how i wear my vacation resort look

Nora of Jacket Society tells us this about her vacation look:

“I am wearing our Black and White Paisley trapeze handkerchief hem tunic/dress with our Ivory marbleized stone necklace, black Trouve’ sandals and Gucci bag. This piece can be work as a dress but you do need to wear leggings or short skirt or shorts underneath.  I am wearing short leggings with it in this photo.  Both pieces are available on our web site.”

How I Wear My Vacation Look Nora

Jacqueline of Petite Silver Vixen says:

“I inevitably pack a maxi dress or two when going on a summer holiday as they’re so easy to wear.  By day you can wear them with sandals or sneakers for leisurely sightseeing or shopping.  For night time you just turn up the glamour with a pair with heels, a pashmina and jewellery.  We visited the village of Saint Paul de Vence, in the South of France last year where the artist Marc Chagall lived and the tropical print and colours of the dress were perfect for the wonderful light and artistic ambience of the Riviera.”

Vacation Look Petite Vixen


Pam of Over 50 Feeling 40 tells us:

“This whole look is from the Chico’s Travelers Collection and what I might wear for dinner at a resort.  The sleeves have a lovely detail and the necklace is designed to look like red seaweed…it is pretty cool.”

how i wear my vacation resort look

Nicole of High Latitude Style says:

“I have a confession to make or may be it’s a warning. I attract rain or may be I am a rainmaker. Wherever I go on vacation, it starts pouring as soon as I set my foot on the ground. I was in Morocco in the Sahara where it hadn’t rained for 3 years. It’s so bad that some friends suggested I should make money from it. Thus, this photo shows my typical vacation style.”

how i wear my vacation resort look

Trina of Tea Time With Trina wears

“Wow, summer has arrived in full swing here in Utah where the daily temperatures are reaching high 80’s already. What a fun idea you two had for this months HIWM theme, I’m sending a resort look I put together while visiting  Florida this year.
This is my version of how I cover up at the beach. I’m not one to really fun around in my bikini any more but I do love a nice coverup that can take me to lunch or a little shopping while I’m at a resort and this one is did both just fine.”

How I Wear My Vacation Look Trina

One of the questions I am asked the most by readers is what to wear when visiting California’s Wine Country. And since nearly all of my travel the last few years has been local, I thought I would wear a look appropriate for a spring, summer or early fall where I live in Sonoma Valley.

This striped drop-waist dress (on sale now) is from Banana Republic. It’s lightweight but it also has a lining so I don’t need to worry about wearing a slip. What I love about it for travel purposes is that I can throw it on and go. All I need is a pair of comfortable shoes and a cute handbag, big enough for my camera and maybe a shawl, and I’m set!

Here I am wearing it with my Adora by Adrienne bag and my three-year-old Lucky Brand sandals (similar).

Vacation look Adrienne

I have also worn this frock a little more dressed up with cognac heels and congac satchel and my black tassel clutch (similar) and block-heeled black sandals.

The true color of the dress is navy blue but it’s dark enough that, when paired with black, it looks black.

How I Wear My Vacation Look

Thank you to all the stylish participants this month! We love how you all wear your vacation and resort looks.

How I Wear My Vacation or Resort Look

Now for next month’s theme:

For July, Jill and I chose “Tunic” as the How I Wear My theme. Show us how you style a tunic top or tunic dress. Whether it’s long or short sleeved, with a collar or without, and includes lace, embroidery, embellishment or is a solid color, we can’t wait to see what you’ll do with your tunic!

Send a photo to us at by July 11, 2016 (we’re pushing things back a bit because of the July 4th holiday) and be sure to tell us a bit about your outfit.

How I Wear My Badge

Be sure to visit Jill’s How I Wear My post for 20+ more vacation and resort looks from our fashionable participants!

Make it a rich day!




  1. June 8, 2016 / 7:06 am

    What a great roundup this month!!
    I love the yellow bag with your dress—that is definitely part of summer to me!

    • Adrienne Shubin
      June 8, 2016 / 7:42 am

      I love carrying that yellow bag – any chance I get now that the weather is warm and the sun is shining. It makes me so happy!
      Hope you and your moms will join us for Tunic next month, Jodie!

  2. June 8, 2016 / 9:32 am

    Another great HIWM series Adrienne! Love you cute dress and the yellow bag. Thank you so much for putting it all together.

    • Adrienne Shubin
      June 8, 2016 / 9:45 am

      Thank you for joining us, Nora! I love your scarf dress…so beautiful and looks very chic the way you’ve styled it. See you next month for Tunic? Kindly, A

  3. Jill
    June 8, 2016 / 9:45 am

    What a great range of looks here. I have accessories on my mind big time so I am loving your yellow bag and Pam’s statement necklace. I also love to see adorable Lars the cat sneaking into Susan’s photo. Cheers to another successful HIWM post!

    • Adrienne Shubin
      June 8, 2016 / 9:50 am

      I love the mix of looks this month, too, Jill!
      My yellow bag is just such a happy thing to carry. I really enjoy making it part of my outfit now that the weather is warm and sunny.
      Thank you for another great month. Looking forward to Tunics! xo

  4. June 8, 2016 / 10:35 am

    So many stylish women and great looks – from dressy to more casual. Appreciate you taking the time to do this. Thanks!

    • Adrienne Shubin
      June 8, 2016 / 10:42 am

      Thank you for joining us, Christine. I love your beautiful robe/kimonos, by the way!

    • Adrienne Shubin
      June 8, 2016 / 10:45 am

      There are lots of outfits that would work on my upcoming trips, too, Beth! You travel so much, you probably have this travel wardrobe thing down!
      Thanks so much for joining HIWM this month. Hope to see you next month for our Tunic theme! A

  5. June 8, 2016 / 11:00 am

    There are too many great looks to single out one or two. I had to laugh over Nicole’s rain making capacities. I mean … rain in the Sahara? Wow. She must be a rain maker.
    Great to be a part of this line-up.

    • Adrienne Shubin
      June 8, 2016 / 11:03 am

      I know. Crazy about Nicole’s rainmaking powers…she needs to come to California! 😉
      Thanks for participating in this month’s HIWM, Greetje! Love your blouse – especially because it has yellow in it! xo, A

  6. June 8, 2016 / 11:09 am

    What a lovely surprise! 🙂 and a lot of these Ladys I’m not familiar with, so nice to meet them! Thank you.

    • Adrienne Shubin
      June 8, 2016 / 11:49 am

      Hi Nancy,
      Thanks for joining us this month! HIWM is a great way to learn about other fashion bloggers. We hope you’ll join us again next month for Tunics! Adrienne

  7. June 8, 2016 / 3:29 pm

    Another great up of fabulous ladies wearing super cute vacation styles! And I am very excited about next month’s How I Wear My Tunic! In fact, I am wearing a tunic today that I have styled in the most fun way! I can’t wait to share it with you! Expect my entry early his month!


    • Adrienne Shubin
      June 9, 2016 / 9:28 am

      Yay for tunics! I love them too.
      Thanks so much for joining us this month, Shelbee. I tried to buy your cute white dress at Old Navy but they were sold out in my size, darn it!
      See you for the next HIWM!

  8. Kathy
    June 8, 2016 / 7:09 pm

    “Resort” wear was so unfamiliar to me as a native Californian, as we always dressed that way unless we were “dressed up”. It’s only now, that I’m feeling drawn to the concept and find myself packing differently for trips to resorts. All great looks, and I really love that bathrobe!

    • Adrienne Shubin
      June 9, 2016 / 9:27 am

      Me too! Isn’t that robe beautiful? It looks so comfortable too.
      I had never heard of Resort wear either until about 5 years ago.

      • June 10, 2016 / 11:23 am

        Thank you so much Kathy and Adrienne for your kind words!

        (I could never find a robe I liked, so I decided to take a chance and design these to see if other women would like them – they are manufactured in Chicago.)

  9. June 8, 2016 / 8:04 pm

    So many great looks this month. I love your fun dress, so perfect for this time of the year.

    Thank you for hosting and hope you are having a fab week!


    Hope to see you Thursday for TBT Fashion link up.

    • Adrienne Shubin
      June 9, 2016 / 9:26 am

      Thank you for joining HIWM this month, Alice. Love your casual vacation look – so cute!

  10. June 9, 2016 / 1:50 pm

    Nice post. So many ideas..

  11. June 10, 2016 / 10:51 am

    Just stumbled on your great blog! Just what I need, some advice.
    We are visiting California next April and I need to know what to pack! I’m 55, short and a size 16. We are planning to fly to Las Vegas and then drive up the western side of the mountains to gold country and then come down the coast for a week staying at a few places ending in Santa Barbara and flying home from Los Angeles. Advice and help on a suitable travelling wardrobe, what to pack and wear would be much appreciated. Many thanks Jane

    • Adrienne Shubin
      June 11, 2016 / 10:42 am

      Hi Jane,

      I would love to help you! Sounds like you have some time before heading out on your trip. Let me think about this for a little bit and get back to you. Luckily you are traveling when the weather is still pretty cool in both Vegas and California. I would encourage you to check out Une Femme ( – Susan travels often and has some great advice on her blog for packing lightly and smartly. Will be in touch soon!

      • Jane Nash
        June 16, 2016 / 3:01 pm

        Thank you! I shall look forward to hearing from you. Very excited about our trip!

    • Adrienne Shubin
      July 7, 2016 / 1:31 pm

      Hi Jane,
      So sorry for the delay in getting back to you. It is not easy for me to recommend what to pack when I don’t know your style but I can say that lots of layers will be best for that time of year. You will want to bring a jacket or coat for that time of year, especially in the mountains of Gold Country. It can get cold at night and April is not a very warm month.
      If you like to wear jeans, I would bring a pair or two with a little stretch in them (I buy Gap). Make sure they are comfortable and versatile. Also a pair of black pants – like soft and stretchy ponte pants or black jeans would be a good basic. Add some neutral tops – 3/4 or long sleeved like the ones made by Covered Perfectly are fantastic for layering – then some sweaters, either pullover or cardigan, to wear over your tops. I also always bring a big scarf along with me whenever I travel – make sure it’s a color that goes with everything (like black). Comfortable shoes are a must. Don’t wait until the last minute to buy new ones. Buy them early and break them in, make sure they are comfy for lots of walking. Supplement your travel wardrobe with accessories like silk scarves, statement necklaces, belts, and earrings. Bring one everyday bag that is big enough to keep your belongings in and is a neutral shade (I like bone/beige colors or cognac). And one clutch for going out.
      I hope that helps! Enjoy your trip! Adrienne

  12. June 11, 2016 / 4:59 am

    Sorry I’m tardy to the party, but it was worth the wait … what a FUN THEME!!! Love seeing everyone in their vacay clothes and poolside or at the beach! How boring my pics are in my yard, but oh well! 😉 Thanks for hosting such a fun party! I’m in for tunics! 😀

    Dawn Lucy

  13. June 11, 2016 / 10:44 am

    so many amazing looks, I love this feature. Every month I look forward to seeing what everyone is wearing

    • Adrienne Shubin
      June 13, 2016 / 5:06 pm

      Me too! See you next time for Tunic? Thank you for participating, Linda! xo, A

  14. June 13, 2016 / 9:09 am

    Perfect timing as I pull out my suitcase to pack for our Summer vacation this year! And there is tons of great inspiration in this post – it reminds me to pack a hat. Thank you for hosting and I love your breezy dress, Adrienne, along with those Lucky sandals – just perfect for the warm weather. (Just bought a natural leather color pair myself – did not even know they made shoes!)
    Enjoy the summer,

  15. June 21, 2016 / 4:02 pm

    Apologies for not replying until now, Adrienne. How delightful it was to see I was included in the collective photo! A lovely surprise. And a real treat seeing so many different holiday looks.

    Your striped dress looks so fresh and lovely with the yellow bag.

  16. June 22, 2016 / 2:05 am

    Adrienne thank you SO much for featuring my stripey jumpsuit!! I have to admit summer is my favourite month so resort wear is just the best in my eyes. So many lovely ladies, so many lovely looks – your dress is super-cute and I’m always a sucker for a bright bag, that yellow is gorgeous!!

    Catherine x

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