Vintage Vacation Outfit Ideas | Retro Holiday

With only one more week of school, my family is ready to start our season of summer vacations! We took a spring break vacation to Disney World and a Disney cruise to the Caribbean in April, and yet here we are about to go on more mini vacations. I love summer for this very reason. We visit my mom in the Bay area (she has a pool!) and take our vintage trailer out for camping in the mountains with friends. If Oscar and I are lucky, we might even get a 24-hour escape to a resort for a night or day trip to nearby historical cities. It’s a busy season, but so much fun too!

Naturally, whenever I go on vacation, I MUST buy a new wardrobe to match the theme and destination. For my cruise, I sought out summer dresses, sandals, and swimwear in nautical themes. Because it was a Disney cruise, I made sure we all had Disney character clothing for at least one dress up night. Even when camping, I make sure to bring layers of clothing that can get dirty yet still complement our vintage campsite.

I have some outfit ideas to share with you today, inspired by popular vacation types: Camping, Cruise, Resort, and Disney — all with a vintage flair. Each outfit also comes from TopVintage, who is sponsoring this article. TopVintage is based in the Netherlands but ships worldwide. They have a HUGE assortment of vintage clothes, organized by decade and style, from European and USA brands. I love their selection, especially the European brands which are hard to find in the USA. I also love that they offer free shipping to the USA as well as UK, LU, NL, BE, DE, FR, AT, and DK.

Every item at TopVintage is measured and tried on for customized fit advice (the size charts are custom made for each and every item). This means it is far less likely you would need to exchange an item for another size. I really appreciate this assurance when shopping with them.

On to the outfits!

Vintage Camping Outfits

1951, camping in rolled up jeans and a knit tops with cute neck scarp and canvas shoes

My sister’s camping outfit- rolled jeans, bandana print shirt, thin belt, and Converse shoes

How to dress in pinup/vintage ’50s style while camping? This question came up recently in a pinup discussion forum which spurred some great ideas. Some women said they wore dresses, usually washable cotton or older dresses they didn’t mind getting dirty.  For a ’60s look, pairing leggings with a knit shift dress was another idea that is both dressy and casual.

I wouldn’t mind wearing a dress for a quick photo op but dresses + camping is not for me. I prefer a good pair of ’50s style dark denim jeans or overalls and a plaid button down skirt. It is dirtproof and durable.

If it is hot, I would swap out jeans for longer length shorts (pedal pushers or Bermuda shorts) and a sleeveless cotton blouse or striped ringer T-shirt. For shoes, classic black converse or canvas Keds Champion shoes are good for around the campsite. A bandana or hair scarf keeps my hair out of the way and covers up the haven’t-been-washed-in days grime.

If you want to see what vintage women wore while camping, take a look at these vintage hiking and camping photos.

Vintage Camping Essentials:

• Plaid shirts/western, wool Pendelton shirts, sleeveless tie tops, ringer T-shirts
• Capri pants, denim jeans, overalls, high waisted shorts/pedal pushers/Bermuda
• Converse shoes, Keds champion, lace up boots, rain boots
• Leggings + a 60s short dress or 50s swing dress (washable cotton)
• Hair bandana and neck scarf

Shop these denim jeans, overalls, and shorts at TopVintage.

Vintage Cruise Outfits

I have been on three Caribbean cruises in the past 10 years and each time, I dressed for the tropical heat with additional layers for the often too-cool air conditioning and windy nights on the deck. My outfits usually consisted of white dresses, nautical striped dresses/skirts, ’50s swimsuit(s), cardigan sweaters, sandals, a wide brim hat,e and sunglasses. The sailor dresses/nautical outfits/tropical prints are very popular on cruise ships. Blue and white stripes, red stripes, yellow and blue stripes, anchors, sailboats, lobsters, and crabs are just a few themes to keep in mind. Shop here.

Days in port were time to explore the islands in comfortable walking clothes (shorts, t-shirt, sneakers, hat) while evenings and at-sea days were a time to dress up for the nightly photo ops. Most cruise lines have a semi-formal and formal night where passengers are encouraged (some required) to dress in evening gowns or cocktail attire. It’s up to you how you want to dress for those nights.

Here are some of my/my sister’s outfits:

Notice how Oscar dressed to match me for most of our photo ops. Cruise attire for men could include tropical shirts/Hawaiian shirts/guayabera shirts, a straw fedora hat, wide leg pants/shorts, and a dinner jacket. We did an all-white look for our first formal night and opted for slightly more semi-formal outfits once we had kids.

Not all cruises travel somewhere tropical. A European river cruise, Mediterranean cruise, or Alaskan cruise will require different clothes. The nautical look can still be used, or you can choose something to match the destination. Outdoors/camping clothes for Alaska. All white for the Mediterranean. River cruise…. hmm, I am not sure about that one. It is on my list of vacations to take, so I am sure I’ll have to figure it out sooner than later.

Cruise Essentials

• Nautical dresses with cardigan sweaters
• Formal dresses, cocktail dresses
• Sailor swimsuit and cover up
• Shorts/sleeveless tops

Shop nautical / sailor outfits at TopVintage.net

Vintage Resort Outfits

Similar to going on a southern cruise, heading out to a beachside resort (Hawaii anyone?) will have you seeking out tropical prints and tiki dresses. I love the tiki room at Disneyland/World, so I wore my tiki print Disney dress and made matching camp shirts for my boys. My daughter’s dress and husband’s tie also matched :). I also brought along flamingo prints, palm prints, sarong dresses, teal and coral everything (my favorite summer colors), white wedges/sandals, and some flower hair clips.

Pool time in vintage swimwear

I like summer dresses that are light and airy for evening dinners and slip over knit dresses for the daytime. I usually bring one pair of capri pants and a nice blouse for nights when I’m too tired to dress up. Jumpsuits or palazzo pants are also really nice options that go from day to night. Rompers/playsuits are great for exploring the local daytime scene or walking the beach without wearing a swimsuit.

When I am going south to a resort in Mexico or the desert, I like the idea of pairing a peasant skirt and blouse together with Mexican huarache sandals. It is another versatile look that is very easy to put together.

Resort Essentials

• Sundress, tropical prints, sarong tiki dress
• Sun hat, sunglasses
• Sandals or wedges
• Romper/playsuit or jumpsuit/palazzo pants
• Evening outfits
• Peasant tops, skirts

Shop tropical outfits at TopVintage

Vintage Disney Vacation Outfits (Bounding)

The best thing about Disney for fans of vintage is the explosion of Dapper Day/ Disney bounding / Retro Disney themed outfits. The idea is, you pick a Disney character and figure out how to look like them wearing 1950s clothing. It doesn’t have to be ’50s, but that is what most people wear. It also doesn’t have to be a character- a Disney theme could be a favorite ride, drink, destination, or general vintage decade. I have helped my sister find outfits for a Lapu Lapu pineapple drink, the Polynesian resort, Ellie (Safari guide) from UP, and an Around the World at Epcot outfit.

Disney has caught onto this trend and now sells a special line of Disney themed dresses, girls’ dresses, and men’s ties and accessories at theme parks and online. Finding Disney themed clothing is pretty easy, as more stores have included them among regular stock. At the very least, polka dot dresses and accessories naturally lend themselves to a Minnie Mouse theme.

For a Disney vacation, it would be impossible NOT to bring a Disney outfit or two, or buy one while at the parks. Many families dress in matching shirts or outfits as well.

Let the vintage clothes at TopVintage inspire your Disney character outfit. I think it easier to let a dress or outfit inspire you, rather than starting with a character in mind and then trying to make the outfit. Either way, have fun with it and dress for comfort above all else.

Disney Vacation Essentials

• Character outfits /Themed outfit
• Mouse shoes or Keds and Converse are also great for a lot of walking
• Mouse Ears or Disney theme sunglasses
• Disney T-shirt- order matching group T-shirts on Etsy
• Pins- Collect and wear Disney pins on a lanyard or purse strap

See more TopVintage summer outfit ideas here.

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