Vintage Dress Fashion Shopping Guide

Vintage style clothing is back in fashion. Everywhere I look I see elements of 20s, 30s, 40s and 50s style dresses, shirts, and accessories in new modern clothing as well vintage reproduction clothing. If you are new to vintage fashion you may not know what to look for when you shop. Here is my quick guide to buying new vintage style clothing or pin up dresses online:

Rockabilly Style

Rockabilly is a fashion and lifestyle culture popular in the southern and western areas of the United States. It’s technical definition is as a music genre popular in the 1950s, combining the influences of R&B with country hillbilly music from the ’40s and ’50s.Today, rockabilly music, lifestyle and fashion lives on in states like California, Tennessee, Washington and Nevada. The subculture of rockabilly isn’t as popular on the East coast – at least for now. Viva! is a weekend of fashion and events around the ’50s rock ‘n roll inspired culture, offering music performances, car shows and quintessential ’50s activities like bowling and bingo.

How to Wear it: Rockabilly is about dressing sexy while still maintaining a unique edge. It combines the ’50s New Look styles with the Bettie Page pin-up looks of the ’40s and ’50s. The stereotypical rockabilly girl is commonly seen with coiffed hair, tattoos and wing tip eyeliner while wearing a 1950s dress, cat eye sunglasses and stilettos. But that isn’t the only way you can dress rockabilly. Even just adding the makeup, or wearing a look like Jasmin from Vintage Vandal above, captures the rock-chic glam of this ’50s look. Red and black is a common color combo for the quintessential rockabilly look. Jasmin went for an all black-red look, including her vintage accessories. The bandanna is a ’40s Rosie the Riveter touch that in my personal honesty, makes the outfit an A+ versus just an A.

Hot Housewife Style

During the baby boomer era of the ’50s, the average age of marrying was 20.3 years old. Today, it’s 26.1 years old. By the mid ’50s, approximately a quarter of married women were working. If a woman was left to cook, clean and care for the kids, she wasn’t wearing Uggs and sweatpants in the ’50s. She was still dressed to impress, protecting her house dress with a pretty apron and when the chores became too much, resting on the stovetop with a glass of wine and a smoke.

How to Wear It: You don’t have to be a real housewife to wear this look, which for modern day is more appropriately worn for events beyond the comforts of your home. These are dresses that feel best for school, social events and just looking really good when you want to get out of those sweatpants. Any 1950s sundress or shirtwaist dress paired with crinoline lays the foundation for the look. The accessories and shoes are up to you. For a bonafide ’50s look, accessorize with a matching earrings, necklace and bracelet jewelry set. Or, skip going all ’50s and pair your dress with a contrasting pair of solid or patterned tights, dazzle up that hair and heck, wear a bunch of cocktail rings on one hand. Whatever feels good for the inner hot housewife in you.

Pin Up Style

You can’t be anything but eye candy in vintage inspired pin up dresses with A-line, pencil or circle skirts that dance with your every step. A wide cinch belt helps define your waist and add a contrasting color to your pinup fashion. The strapless, spaghetti or halter neck pin up dresses are the most popular 50s pinup clothing for summer. Pin up dresses with sleeves are harder to find however with a little crop or cardigan sweater sleeveless dresses are wearable all year long.

Modern pin up girls provide plenty of inspiration for how to wear 1940s and 1950s pin up dresses in a fresh way: Mix and match swing dresses with colorful fluffy petticoats and a hair flower. A wiggle pin up dress ads a sexier variety that can also be office appropriate with a matching jacket. Don’t forget seamed stockings and a comfortable but oh-so-sexy pair of wedge heels or casual ballet flats. Think beyond the pin up dress with high waisted pants and shorts or swing skirts and tops. Use the 40s and 50s menus at the top for more pin up clothing.

Polka Dot Style

Who doesn’t love polka dots? Shop for a fun retro vintage polka dot dress that embraces vintage fashion from the 1930s, 1940s and 1950s. Vintage polka dot dresses first appeared in the 1920s but it was the teenagers in the 1940s that loved them so much they kept wearing them into the 50s. Halter dresses, wiggle dresses, swing dresses, circle skirts, and tops are all styled in splashes of ditsy dots. Black and white polka dot dresses, white polka dot dresses, navy polka dot dresses, red and white or red and black polka dot dresses in big and small dots! So many cute choices in regular, petite and plus sizes.

Plus Size Dresses

Plus size swing dresses, plus size rockabilly dresses and plus size pin up dresses take inspiration from the classic silhouettes of the 1950s. The sexy plus size wiggle dress or pencil dress hugs curves in all the right places (sometimes with the help of shapewear.) The full skirted 50s plus size swing dress is the preferred style for day to day wear, especially among pinup and rockabilly fashion followers. Thankfully the vintage inspired plus size clothing industry has expanded to include dozens of vintage & retro clothing brand such as Hell Bunny, Stop Staring, Dolly and Dotty, Lady V London, and Unique Vintage as well as at mainstream stores such as Torrid and Hot Topic.

We searched for some of the best retro 1950s plus size dresses and plus size swing dresses online to make your shopping easier.

Floral Dress Style

Ever since WWII ended in the 1940s, Hawaiian print shirts, sarong dresses, and tropical flowers have been popular fashion wear. Men and Women of the late 1940s, 1950s and early 1960s hosted poolside “Tiki” parties complete with tropical drinks with little pink umbrellas. Restaurants and dance halls picked up on the fad and held tiki-themed dances with lounge style musicians. To dress for the occasion women wore tropical print dresses also called tiki dresses. Many were inspired by Hawaiian life in the 1940s after the bombing of Pearl Harbor put Hawaiian shirts and dresses in the spotlight. Scroll down read the history of the tiki dress or shop these retro tiki dresses, tropical dresses, floral dresses, Hawaiian shirts, and accessories. Don’t forget to add a pair of retro sandals, a hair flower, jewelry, and parasol, to your tiki dress.