Best 15 Pin Up Dress Outfit Ideas: Style Guide for Ladies

best pin up dress outfit ideas for women

For those of you who don’t exactly know what the pin up dress means, they are simply dresses that has a gathered waist cutting and the waist area of the dress sometimes have pins attached to them. In other words, they are simply dresses that has a very tightly fitted cutting at the waist area. A lot of time, they come in the form of fit and flare dress which is a nice way to make yourself look lean and tall. To show you some examples of how to style it, I have collected some good pin up dress outfit ideas for you. Let’s check them out now.

Burgundy Deep V Neck Half Sleeve Pin Up Flared Midi Dress


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To kick start this list of outfit ideas, you can wear a deep red or burgundy v neck half sleeve pin up midi fit and flare dress. For the shoes, you can wear a pair of black strappy round toe heels to look vintage and unique. You can add a black leather purse to complete this elegant and vintage look.

Black and Red Pin Up Fit and Flare Midi Dress with White Lace Choker

black and red pin up fit and flare midi dress with white lace choker
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This is another vintage dress that can make you look very attractive in a cocktail party. The dress is a black pin up fit and flare midi dress that comes with a red belt which also comes with some nifty pins. Wear it with a white lace collar-like choker to look elegant and feminine. Pair them with black leather heels to wrap up the look.

Black and White Striped Two-Toned Pin Up Flared Midi Dress

black and white striped two toned pin up flared midi dress
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Here is a more youthful and stylish outfit that you may want to try. In detail, the dress is a two-toned flared midi pin up dress, with the upper part filled with black and white pattern and the lower part being a black midi flared skirt. Pair them with a pair of black ballet suede heels to look elegant and clean.

Black and Red Pin Up Halter Neck Midi Dress

black and red pin up halter neck midi dress
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To form this sharp and vintage look, the use of the color combination of red and black is the key. To achieve this look, you can wear a black and red halter neck pin up midi bodycon dress. Pair it with a pair of red rounded toe heels. Add a black and white polka dot purse to complete the vintage look.

Black and White Checkered Fit and Flare Square Neckline Midi Dress

black and white checkered fit and flare square neckline midi dress
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To form this attractive vintage cocktail party outfit, you can wear a black and white plaid fit and flare midi pink up dress that comes with a square neckline design. Pair the dress with black ankle strap open toe heels to look lean and tall. You can wear black gloves to look even more ladylike and vintage.

White Off The Shoulder Flared Midi Dress with Red Polka Dot Pattern

white off the shoulder flared midi dress with red polka dot pattern
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Here is an outfit that can make you look low-key sexy without requiring you to show way too much skin. To achieve this outfit, you can simply wear a two-toned dress that consists of a white off the shoulder short sleeve fitted t shirt upper part and a red and white polka dot flared midi pin up skirt lower part. Wear gold open toe heels to wrap up the outfit.

Black Midi Bodycon Pin Up Dress with Sheer Overlay

black midi bodycon pin up dress with sheer overlay
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This is a breezy and elegant cocktail party outfit that can make you stand out from the crowd in a natural way. To form this look, wear a black bodycon midi pin up dress and layer a black semi-sheer overlaying scarf over it. Pair them with black open toe heels to complete the outfit with style.

Red and Black V Neck Cap Sleeve Pleated Flared Midi Dress

red and black v neck cap sleeve pleated flared midi dress
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This is a very attractive black and red vintage outfit. To form this eye catching yet natural look, you can wear this red and black v neck pleated flared pin up dress that is filled with color blocks and polka dot pattern. For the rest of the outfit, you can wear a pair of red ankle strap open toe heels to wrap up the look.

Blue and White Halter Neck Fit and Flare Sweetheart Neckline Dress

blue and white halter neck fit and flare sweetheart neckline dress
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While a black and white checkered dress is a classic dress that can make you look great, a blue and white checkered dress like this fit and flare midi pin up dress isn’t too shabby either. For the rest of the outfit, you can wear a pair of blue ankle strap open toe heels to complete the outfit.

Black Criss Cross Neck Pleated Knee Length Pin Up Shirt

black criss cross neck pleated knee length pin up shirt
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To form this all-black elegant cocktail party outfit, you can wear this black criss cross neck fit and flare knee length pleated dress as the focal point of your outfit. Pair it with a pair of black ankle strap open toe heels. A black leather purse would look awesome with this outfit.

Black Low Cut Knee Length Bodycon Dress with Leather Heels

black low cut knee length bodycon dress with leather heels
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This outfit is a great demonstration of the concept “less is more”. To form this minimal and attractive look, you can simply wear a black short sleeve low cut bodycon mini pin up dress to show some curves. Pair it with a pair of black leather high heels to keep the outfit simple and clean.

Red and White Polka Dot Fit and Flare Pin Up Dress

red and white polka dot fit and flare pin up dress
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To form this vintage and eye catching look, you can wear a red and white polka dot fit and flare midi tank dress. Pair it with a pair of red open toe heels to match with the dress perfectly.

Black and Grey Polka Dot Flare Midi Dress

black and grey polka dot flare midi dress
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Here is another vintage outfit that makes use of the classic polka dot element. To form this look, you can wear a black and grey cap sleeve polka dot midi flare pin up dress. Pair the dress with a red ribbon suede high heels to wrap up the outfit with an eye catching touch.

I hope you like the pin up dress outfit ideas that I have just shared with you in the above list. Try them on to see if they fit your body type well enough.