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What I’d Wear on a Cruise This Fall/Winter
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items If I were booking a cruise this fall or winter, this is exactly what I’d want in my suitcase. Think breezy dresses, coastal stripes, matching sets, woven accessories, easy sandals and plenty of swimsuits for those warm-weather port days. Basically, m...
Sections
8
Dresses
Tops
Bottoms
Matching Sets
Bags
Shoes
Dresses
The dresses I’d pack first for a fall or winter cruise.
The kind of dress I’d throw on the second I get on the ship. The blue stripes and crochet detail are giving effortless nautical without going full sailor.
Ocean Stripe Crochet Brookside Mini Dress
An easy daytime dress for wandering the ship, grabbing lunch or heading into port. Comfortable, but still cute enough that I’d feel put together.
Z Supply Catamaran Dress
For the days when I want something breezy and effortless. I’d wear this over a swimsuit or with sandals for exploring a port.
Petal & Pup Hollywell Openwork Embroidered Maxi Dress
This feels like the perfect sunset dinner dress. The eyelet detail makes it feel special without being too formal.
Petal & Pup Merletto Short Sleeve Cutout Eyelet Maxi Dress
This is probably the most “me” dress of the bunch. Classic navy, feminine and polished, with just enough vacation energy.
The Margot Dress
A classic white eyelet dress belongs in every warm-weather suitcase. I’d wear this for breakfast, lunch or a casual afternoon off the ship.
Eyelet Shift Dress
I love a good crochet dress for vacation. This would be perfect over a swimsuit during the day or dressed up with sandals for dinner.
Crochet Sleeveless Midi Dress
The one I’d save for a really nice dinner. I love the blue and white combination, and the floral makes it feel a little more special than an everyday vacation dress.
Cherie Jacquard Midi
Tops
Easy tops for layering, exploring ports and making cruise outfits feel polished without trying too hard.
A perfect little white tank for layering under everything. I’d wear this with trousers, shorts or a skirt when I want something simple and polished.
White Ric Rac Compression Tank
This is the elevated basic I’d want packed in multiples. The cotton-silk blend makes it feel a little more special than your everyday tank.
White Cotton Silk Vesta Tank
The prettiest option of the bunch. I’d save this for a nicer lunch or afternoon drinks when I want something feminine without putting on a full dress.
The Miro Top
A blue striped tee is basically made for a cruise. I’d wear this with denim for exploring a port or linen pants for an easy lunch onboard.
Blue Striped Presley Boyfriend Tee
I love the idea of this with wide-leg pants and sandals for a day when I want to look pulled together but still feel completely comfortable.
Endless Rose Embroidered Shirt
Bottoms
The bottoms I’d pack for port days, casual lunches and evenings when I want to look a little more polished.
A good pair of denim shorts is coming with me, especially for port days. These have that relaxed vintage feel I love without looking too casual.
Madewell The Perfect Vintage Mid Length Denim Shorts
The best of both worlds for exploring. I love that it looks like a skirt but gives me the practicality of shorts when I’m walking around a new city.
Madewell Denim Wrap Mini Skort
These are exactly what I want for warm evenings on the ship. Easy, breezy and polished enough to wear with a pretty top and sandals for dinner.
Madewell The Zoe Relaxed Straight Pants in 100% Linen
Matching Sets
Matching sets may be a trend, but I think they were made for vacation. One outfit, zero overthinking.
A classic striped button-down is one of those vacation pieces I’d wear constantly. This one gets even better paired with the matching shorts
Blue Stripe Seersucker Nadine Button Down
The matching shorts make this feel like an outfit without requiring any thought. Add sandals and a tote and I’m ready for a port day.
Blue Stripe Seersucker Raven Short
The crochet detail makes this feel instantly vacation-ready. I’d throw it over a swimsuit or wear it with the matching shorts for an easy sea-day outfit.
Blue Grotto Crochet Capri Crewneck
These are such a fun alternative to denim shorts. Paired with the matching crochet top, they make the easiest pool-to-lunch outfit.
Blue Grotto Crochet Positano Shorts
A vacation wardrobe needs a good halter, and I love how easy this one is. Pair it with the matching shorts or wear it with linen pants for a different look.
LSPACE Milly Halter Top
These feel like the shorts I’d live in on vacation. Comfortable enough for wandering around, but cute enough that I wouldn’t feel underdressed.
LSPACE Billie Shorts
I love the classic, sporty feel of this set. This would be my coffee, breakfast and wandering-around-the-ship uniform.
Polo Ralph Lauren Short Sleeve Shirt & Shorts Set
The eyelet detail makes this feel so pretty and summery. I’d wear it with the matching maxi skirt for dinner or mix it with linen pants.
Petal & Pup Camellia Cotton Eyelet Crop Top & Maxi Skirt Set
The dusty blue mosaic print is gorgeous, and I love that this feels feminine without being overly sweet. Definitely a dinner-on-the-ship piece for me.
The Anya Top
This is the kind of skirt that makes an outfit feel instantly finished. With the matching top, it’s basically vacation dressing on easy mode.
The Tyla Skirt
For the active part of the vacation wardrobe. I’d wear this for a morning workout, walking around port or a very casual sea day.
lululemon Align™ Tank Top
The shorts I’d pack for those days when comfort is the priority. I love that the matching tank makes them feel like an actual outfit rather than gym clothes.
Hotty Hot High-Rise Lined Short
Bags
The bags I’d bring for port days, pool days and every dinner in between.
This is the port-day bag I’d want when I need my hands free. Small, cute and actually practical for walking around somewhere new.
Clare V. Petite Fanny Rattan Woven Leather Belt Bag
I love a raffia clutch for vacation evenings. The cognac leather keeps it feeling classic instead of overly beachy.
Cognac and Raffia Lock Clutch
Such a pretty little dinner bag. This is the one I’d reach for when the dress is doing most of the talking.
Clare V. Petit Pot De Miel Bag
This is giving me pool deck, sunscreen, sunglasses and a book. Basically everything I want within arm’s reach on a sea day.
Madewell The Eyelet Raffia Shopper Tote
The classic vacation tote. I’d use this for the beach, pool or a full day exploring a port.
Sophie canvas-trimmed woven straw tote
I love this as the more polished option. It could easily go from sightseeing during the day to dinner without looking like a beach bag.
Reformation Medium Vittoria Tote Bag
Shoes
The vacation shoes I’d actually pack, from dinner sandals to all-day walking pairs.
The kind of neutral sandal that makes every vacation dress look a little more polished. This would absolutely come to dinner with me.
Helen Sandal in Natural
A classic espadrille wedge feels made for vacation. I’d wear these with a sundress for dinner or drinks on the ship.
Soludos Marseille Wedge Espadrilles
For when I want a flip-flop that still looks intentional. The braided detail makes these feel a little more elevated than the average beach sandal.
TKEES Lily Braid Bourbon Flip Flops
An easy slide is non-negotiable for a cruise. These would be my grab-and-go pair for breakfast, the pool and everything in between.
The Buckle Slide
I love these for a slightly dressier daytime look. The woven texture makes them feel vacation-ready while the Mary Jane shape keeps them classic.
Maren Woven Mary Jane Flat
These are the practical pair I’d want for a full day exploring a port. Comfortable, easy and still cute enough for vacation photos.
CROCS Miami Toe Loop Sandal
For the days when I know I’m going to be walking approximately 47,000 steps around a port. A classic sneaker always earns its suitcase space.
Keds® Champion Sneaker
My pick for the most fashion-forward walking shoe. These would be especially good with shorts, matching sets and casual dresses.
New Balance 327 Sneaker Women
Accessories
The little extras that make a vacation outfit feel finished, from statement earrings to the perfect sunglasses.
A vacation hat is non-negotiable for me. This is the kind I’d throw on for the pool, a port day or breakfast on the deck.
Sand Waverly Hat
A good pair of oversized sunglasses can make even a basic swimsuit and cover-up look intentional. I love the tortoise for vacation.
AIRE Whirlpool Aviator Sunglasses
These feel a little more fashion-forward than the classic aviator. I’d pack these for days when I want the sunglasses to be part of the outfit.
Eyeking East West Oval Sunglasses
The easiest way to make a simple dress or linen shorts feel more pulled together. I love a good belt for breaking up an otherwise simple vacation outfit.
Madewell Lucie Belt
These are the earrings I’d pack when I want a simple outfit to feel instantly more dressed up. Perfect for dinner without being too formal.
Gold Constantine Earrings
The white detail makes these feel especially good with vacation whites, linen and blue. I’d save them for a pretty daytime outfit.
Rose Quartz Juno Earrings
A little bit of colour without going full statement earring. These would be so pretty with a simple sundress.
White Sundial Earrings
You can never go wrong with a good hoop on vacation. These are the pair I’d wear when I want something classic that works with basically everything.
Concetta Hoop Earrings
These feel made for a cruise dinner. They add that slightly polished, feminine touch without making the outfit feel overly formal.
Pearl Cluster Earrings
A classic baseball cap is a vacation essential, especially for casual port days or mornings when I want to hide from the sun and still look put together.
Polo Ralph Lauren Chino Sport Cap
I love a little unexpected colour in a vacation wardrobe, and butter yellow is such a good one. This would be such a cute finishing piece with denim or white linen.
Butter Yellow Organic Cotton Stretch Twill
Swimwear
The swimwear I’d pack for pool days, beach stops and pretending I live on a cruise ship.
The perfect playful vacation bikini. The teal gingham feels especially cute for a cruise somewhere warm.
The Juno Bikini Set
I love a good classic bikini, and this one feels like something I’d reach for again and again on vacation.
Hill House Home The Teagan Bikini Set
A striped one-piece is such a timeless vacation choice. This would look just as good with shorts thrown over it for walking around the ship.
jetty stripe scoop neck one piece
For when I want the ease of a one-piece but still want it to feel special. The blue is so pretty for a sunny vacation.
The Emerson One Piece
This is the more polished one-piece I’d pack for lounging somewhere fabulous. It feels a little more elevated than your average swimsuit.
STAUD Adelaide One Piece
A statement swimsuit for when I want the swimsuit to be the outfit. I’d absolutely pair this with oversized sunglasses and a big hat.
STAUD Dolce One Piece