Vintage Sailor Clothes, Nautical Theme Clothing 1920s-1950s

1958 nautical outfits

My tulips are coming out of hibernation, and the early morning chirping of the birds is telling me spring is here. I am looking forward to warmer weather, sunglasses, and lighter colors. I remember meeting a friend one warm spring day at the mall. I was wearing a blue and white striped dress and she was in shorts and a blue striped shirt.

As we people watched, we noticed everyone else was also in nautical colors – blue, white, yellow, and red.  This mass migration to the sea side (even if only in our wardrobes) has been going on for all of the 20th century. Vintage clothing, especially, has embraced nautical or sailor themed clothing as icons for summer play time. Swimming, biking, or shopping was all done in nautical sailor themed style.

Here are some vintage pictures of how nautical colors and sailor inspired designs have played a part in fashion from the 1920s to 1950s, followed by a few outfit ideas to get you ready for spring, summer, or a themed cruise vacation.

1920s Sailor Clothing

1922 Seaside colors- red and blue striped  hat and blue cardigan over white dress.

One of the most popular women’s sport clothes / casual outfits of the 1920s was the Middy top and skirt. It was a style directly copied from men’s official sailor uniforms, but fitted for women. A loose white or blue pullover shirt with a blue red or neck tie scarf and distinctive sailor flap made up this new style for women (although little children had been wearing it for many years prior).

The middy top was paired with a blue, black or white/cream colored skirt. Casual low heel oxfords, heels or canvas sport shoes (Such as Keds Champion) completed a basic outfit.

Middy blouses are not easy to find today although I often find 1980s nautical blouses and dresses that look similar.  Another source are Cosplay costumes for “school girl” anime outfits.

1924 Middy blouses

As the roaring twenties danced on, white, blue, and red separates were mixed together for nautical inspired spring fashions. Sweaters and jackets layered over a white dress or skirt was the easiest mix. A blue or red scarf, hat and belt added even more variety. The color combination made the nautical look and it hasn’t left fashion since.

1928, again a white dress with blue jacket and what I assume is a red or blue polka dot scarf. The white cloche hat with blue band perfectly coordinates.

Sailor dresses were blue or white with a “sailor necktie” looses knotted. Many came with a matching belt or sash placed low around the hips.  See some summer dresses for sale here. 

Here are three 1920s sailing outfit ideas:

Women is the 1920s always wore stockings under dresses. White was best with light colored dresses but black was also worn.

Other accessories were paper parasols, handfans, shawls, and hats such as a cloche, straw boater, or wide brim sun hat. 

Japanese Design Paper Parasol and a sailor dress

1930s Sailor Play Clothes

The 1930s embraced nautical colors and patterns for sportwear even more than the 1920s. Navy blue and white were still the primary patterns, but red took on a bigger role.  Instead of just an accent color, it was the primary color of pants/ beach pajamas/shorts/overalls, skirts and tops too.

1937 wide leg pant, shorts and matching blouses

Instead of solid colors, clothes also came in stripes or nautical flag prints. Plain shirts and pants had Anchors and other nautical motifs embroidered on pockets and cuffs.

1938 nautical sport outfits

1930s sailor themed outfits

Carole Lombard, 1934, in a matching navy blue sailor shirt and striped pant.

Stripes, buttons, and anchors appeared on most 1930s nautical clothes. Stripes were seen running down the length of pant legs, while contrasting white or navy buttons appeared on the front pant flap. They appearance was again copied from men’s sailor uniforms.

1938 Cotton or Denim Sailor Pants

The middy blouse remained popular, but now women also had man-tailored blouses with pointed collars and small bows that combined the masculine and feminine together.

1937 Summer shoes in nautical colors

Even shoes were coordinated with nautical play clothes. Sporty tennis shoes, sandals, loafers, saddle Oxfords, and ghillies were all offered in blue and white, red and white, brown and white, and sometimes red and blue combinations.  I love these. Sign me up for a pair of each!

Nautical color summer dresses

The nautical color palette made its way to day dresses too. The middy top dress with “X” ties on the right is the most sailor inspired while the other dresses blend red, white and blue for a more subtle nautical style.

1932 Sleeveless jacket for this nautical outfit

1930s style clothing: Dresses, tops, skirts, shorts, pants, shoes.

More 1930s outfit ideas:

1940s Nautical Clothes

In the 1940s, high waisted navy pants with buttons continued to be very popular. The anchor motif appeared on every bit of clothing possible from pants to tops to playsuits.  With World War II in full force, the nautical red white and blue color scheme doubled as patriotic support. Instead of only appearing during spring and summer, patriotic colors were worn year round.

1945 Candy Stripes and a Blue Suit- nautical or patriotic?

I love that her outfit matches her Captain husband.

Of course, the nautical look was still worn as a mark of spring/summer, too. Stripes became even more common in the 1940s, both on dresses and play clothes. Shop 1940s and 1950s sailor themed clothing. 

1940s summer nautical dresses and blue and white

1947 stripe shirt with denim shorts

1950s Nautical Style

Dresses in the 1950s continued to have nautical elements, but by the mid ’50s the fascination with cute anchor motifs, stripes, and buttons was almost gone. Instead, fashion took on a more sophisticated inspiration of nautical colors and design details. Red, white, and blue were incorporated together into not-so-obvious patterns.

Pink often replaced red as the new hot color of the 1950s. The overall look was still there, but it wasn’t a literal interpretation. By the 1960s, there was almost no sign of anything nautical left in fashion. It wouldn’t come back again until the 1980s.

Shop 1940s and 1950s sailor themed clothing. 

1950s two sailor themed swing dresses

50s Sailor themed clothing in plus sizes

1953 Nautical Dress with matching gloves. So cute!

1950s red, white blue dress, not obviously nautical

The classic Middy top was refashioned into the sailor top which had a more feminine and sophisticated style. Matching mother and child looks were very popular.

Red, white and blue casual sportswear.

1953- Play clothes were the one clothing style that kept the nautical look alive in the early 50s. The embroidered anchors are adorable.

Vintage Sailor / Nautical Style Today

It is no surprise that vintage style lovin’ gals gravitate towards sailor or nautical themed clothing each spring. They are just too darn cute not to wear! Here are some outfit ideas to inspire your spring wardrobe:

Look for sailor themed dresses, shorts, pants, tops, sweaters and skirts, too.

Modcloth has a lot of cute sailor themed clothing from dresses to tops, skirts, shoes and hair accessories.