Date Night | Cruise Style

Happy Monday from the land of jet lag and laundry! There’s no question the last few weeks have been a whirlwind of travel, and while I’m beyond grateful for the opportunities, nothing beats the feeling of coming home!

I put Little Miss to bed last night, and lingered long after she’d fallen asleep just staring at her precious face. She was happy to have us back, but even more thrilled to add to her snow globe collection! (We bring one home from each of our travels, see her room and collection here.) I think our son was mostly just excited to be relieved of taxi duty. He finally got a little taste of what the last 16-years has looked like for us!

Today I’m excited to share some Date Night inspiration with you, perfect for Fall and holiday parties and events. One of the most-fun parts of cruising, is every night is date night! I took a handful of dresses and jazzy tops, but this lace fit-and-flare was by far my favorite.

Jacket | No-Iron Dress Shirt | Trousers | Shoes (similar for less) | SunglassesLace Fit-and-Flare Dress | Sandals

I actually shared several dress options on my Instagram Story when packing (find them in my highlights under Cruise Packing), and this was your overwhelming favorite, too. Nordstrom is jam-packed with so many gorgeous dresses for every dress code, so it was impossible to choose just one!

The shape is so classic and flattering, but the navy and black color block, along with the tiered skirt, makes it extra-chic and modern. The lace is thick and substantial, and it’s fully-lined (with the exception of the shoulder cut-outs).

I paired it with nude sandals, but black pumps would be a great option when it cools off even more. I also kept my accessories neutral to allow the lace and details of the dress shine.

Fit Tip: I’m wearing a regular 2 and it falls just above my knee. I’m 5’4″, btw.

Earrings | Cuff | Lipstick

Can you believe the views from our ship? These were taken on the British Isle trip, which has a lot of open seas between ports. Alaska was completely different in that we saw land and rugged coastline for much of the journey.

We’ve loved all the ships, but the Regal and Royal are our favorites of the Princess fleet. They’re among the newest and largest, with more wide-open deck space and the gorgeous Skywalk over the ocean.

Lace Fit-and-Flare Dress | Sandals | Earrings | Cuff | Lipstick

It’s always a fun time with Mr. SP, but our hilarious friend, Zan Passante of Cling Creative, shot these…hence the extra laughs.

Jacket | No-Iron Dress Shirt | Trousers | Shoes (similar for less) | SunglassesLace Fit-and-Flare Dress | Sandals

We pull out the stops for Formal Night on the ship, but the rest of the time it’s a more casual affair. Here are a few options from the other nights at sea.

Ruffle Sleeve Blouse (on sale!) | Distressed Jeans (similar) | Similar Leopard Pumps

I love this ruffled jumpsuit as a dress-alternative! It’s really comfortable, and the peplum silhouette is extremely flattering.

Fit Tip: I’m wearing a regular 0 and had it hemmed. If you’re in-between sizes though, go up one.

formal night on the cruise ship
Peplum Jumpsuit | Sandals | Leopard Clutch

This shirtdress has seen more action than any other…I take it on virtually every trip! It works for all seasons, and packs like a dream. Not to mention, hides all the eating!

Fit Tip: I’m wearing an XS. 

Shirtdress | Similar Leopard Pumps

You’ve seen this lace midi countless times…it’s my go-to for all things cocktail! But beware, it’s a compliment magnet! (See it in full in this post.)

Fit Tip: It runs small, so size up one. The straps are adjustable for a more custom fit across the bust.

Lace Midi Dress

And finally, this is from last year, but I just saw the gorgeous maxi dress is on sale! (See the full post here.)

Fit Tip: I’m wearing a 2p.

Floral Maxi Dress | Sandals

What’s your go-to date night look for cocktail and formal events? Do you like getting gussied-up, or prefer to keep it casual? I think it’s safe to say we’ll be in sweatpants on the couch for our next few date nights! Takeout tacos are sounding pretty good right now!

See more of our Date Night styles here, and find more about our Princess Cruises here.

[Shop My Formal Night]


[Shop Other Nights at Sea]

*Photos by the talented Zan Passante of Cling Creative. This post is created in collaboration with Nordstrom & ShopStyle, but all styles, opinions, and passion for sea life are my own. Thank you for supporting Hi Sugarplum sponsors!*


Leave a Comment


  1. Yay, I like that you wore your shirt dress to the cruise! It’s my favourite piece of yours. So gorgeous. 🙂

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 9.24.18 Reply
  2. Sandy wrote:

    Such g r e a t photos. Who said what in the laughing photograph?? Love these looks.

    Posted 9.24.18 Reply
    • Cassie wrote:

      Knowing Mr. SP, it was something completely inappropriate! 😉 xo

      Posted 9.25.18 Reply
  3. Sevahn wrote:

    Welcome home, Cassie! The blue lace flit and flare dress is darling on you. I like to get dolled up for date nights too. It’s the best opportunity to present ourselves in the prettiest, most feminine and graceful way. Smiling is the finishing make-up touch that lights up our entire ensemble and brings out our inner beauty.

    Posted 9.24.18 Reply
    • Cassie wrote:

      Thank you so much!! Your comments are always so thoughtful and make my day!! Thank you for spreading your joy! xo

      Posted 9.25.18 Reply
  4. Cassie! You clean up nice! 🙂 Love all of the dresses on you, but the navy lace and the blue floral maxi are absolutely STUNNING!!!!

    Posted 9.24.18 Reply
  5. Taylor wrote:

    I feel like your posts would be more helpful if you didn’t show SO many photos of the same outfit in just one post. We get it after 2-3 photos. I used to be an avid reader but I just can’t anymore.

    Posted 9.24.18 Reply
    • Cassie wrote:

      My goal is to show every angle of the outfit, including special details and all the accessories. The majority of readers request it and find it helpful in determining if they want to add the piece to their own closet! I really appreciate your feedback and taking the time to comment, Taylor!

      Posted 9.25.18 Reply
      • Bev wrote:

        Your photos are amazing! It’s easy to scroll through them too. 😉

        Posted 9.29.18 Reply
  6. Kira wrote:

    Hi Cassie, would you be able to link to the actual pants your husband is wearing? The ones you linked to are solid, not patterned like the ones he is wearing but I really like the patterned ones. Also, is the blazer you linked to the blazer he is wearing? Thanks!

    Posted 9.26.18 Reply
    • Cassie wrote:

      His pants are from last year, but I linked the same ones for this year. And here’s the exact blazer he’s wearing in these pics:

      xo. C

      Posted 9.26.18 Reply
      • Kira wrote:

        Thank you!

        Posted 10.6.18 Reply
  7. Jill Landess wrote:

    I love your blog.:) Do you know if the blue lace fit and flare dress is still available? The link doesn’t work any longer. Thank you!

    Posted 10.17.18 Reply
    • Cassie wrote:

      Thanks so much, Jill! I think there was a tech issue with links earlier, but it’s resolved now. Looks like there are a few of the dresses available! xo

      Posted 10.17.18 Reply
  8. Diane wrote:

    I bought the shirtdress and I LOVE it! I can see why you take it on most trips. One question, do you dry clean it or can it be hand washed? I love your style and you have inspired me to up my game…I’ve use to enjoy dressing stylish but got so caught up in life, raising kids and maintaining my career, in a male dominated technical industry, clothes were not a priority but since I’ve been reading your blog, I am building a wardrobe that is functional, stylish and makes me feel great! Thank you for sharing your great style with people like me who need some inspiration.

    Posted 10.18.18 Reply
    • Cassie wrote:

      You have no idea how happy this makes me!! I’m thrilled you find inspiration here, and will continue to work hard creating new and fresh content for you! As for the dress (yep, it’s a good one!), I wash it on delicate and hang dry!

      Posted 10.18.18 Reply
  9. DeAnn wrote:

    Where did you get your clutch? I love it!

    Posted 10.10.19 Reply
  10. Beth wrote:

    im days away from going on my first cruise and after looking at these photos i feel like in unprepared and that im going to stick out like a sore thumb. i dont own many nice or cute clothes

    Posted 2.20.20 Reply
    • Cassie wrote:

      Hi Beth! I promise you’ll look fantastic…and even more important, you’ll have a blast!! Really anything goes, and if you prefer to stay casual, there will be plenty of restaurants and areas for that!! And some cruise lines are a little dressier than others, but no one says you have to take part in it!! Enjoy your trip! xo. C

      Posted 2.21.20 Reply