20 Pin Up Outfits and Retro-Inspired Ideas to Try

Looking for pin up outfits with polka dots, red accessories or a gorgeous full skirt? There’s plenty to choose from here.

These looks range from fitted dresses and rolled-up jeans to modern casual combinations with little retro details.

You can keep things simple or go all out with curls and long red gloves. If you’ve been saving pin up outfits ideas, start with a favorite shape or color, then pick the accessories you’d actually want to wear.

Pin Up and Retro-Inspired Outfits Worth Saving

polka dots and white heels

We’re starting off strong with this gorgeous white polka-dot dress. I love the square neckline and fitted skirt.

The white pointed heels keep the whole outfit nice and simple.

Try red lipstick and pinned curls if you want to follow the same look.

red checks and dark shorts

How cute is this checked top? The fitted waist and pointed hem look so pretty with the dark shorts.

Tall brown boots and white socks take this in a more casual direction.

Read also: 20 Mauve Outfits and Pretty Pink Looks to Try

For a more classic pin-up variation, you could swap the boots for red flats.

burgundy skirt and black collar

This burgundy dress may just be one of my favorites here. I love the black collar and wide belt, plus that full skirt with a little black edging peeking underneath.

Keep the black bow heels if you want to try the same combination. The long diamond-shaped earrings are a pretty extra touch.

printed shirt and red sandals

If you are looking for something to wear with jeans, this one is for you. The printed collared shirt ties at the waist above a slim red belt.

Those wide rolled cuffs are worth copying too.

Read also: 20 Old Dress to New Dress Ideas to Inspire Your Next Refresh

I especially love the red sandals and matching little bag. Pick one color from your shirt for your own accessories.

gingham top and cropped pants

I am obsessed with this matching gingham set. It’s so cute, plus those little bows on the pointed shoes are adorable.

The pale headband and shoulder bag keep the colors simple. Try a pointed-hem top with matching cropped pants to follow this look.

knotted tee and pencil skirt

Don’t want to go all out and want something super simple? This white tee and black pencil skirt pairing is for you. Knot your tee at the waist like the one here, then add a gold-tone chain necklace.

all-over leopard print

The leopard-print fans are going to love this! The fitted dress has a high round neckline and three-quarter sleeves, with no belt or necklace covering the pattern.

Read also: 20 Triangle Body Shape Outfits With Jeans, Skirts and Pretty Tops

I’d keep the accessories minimal too. The big waves and orange-red lipstick already give you plenty of styling inspo.

cuffed jeans and a red headscarf

This is such a pretty way to wear a plain black top. The wide neckline sits off the shoulders above dark high-waisted jeans with oversized cuffs.

I love the red headscarf with the white flowers beside it. Add red and black bracelets if you want another little splash of color.

navy shirt and bandana bow

Don’t want to build your whole look around a dress? No problem!

Try an open navy shirt over a black top, then tie a red bandana above your forehead.

The rolled front section of hair and long curls are my favorite parts of this look.

bird details and fishnets

How cute are the little birds on this black cardigan? The blue and red details give the otherwise black outfit a bit of color.

A fitted skirt, fishnet tights and glossy strapped shoes complete the combination.

Try a blue hair accessory like the one here to pick up the color in the birds.

red and white stripes

I am obsessed with this striped matching set. The front-tie top and high-waisted shorts look so cute together.

I especially love how the horizontal waistband breaks up the vertical stripes.

Keep the cat-eye glasses if you want that same retro touch.

green layers and striped pants

This one leans more modern and preppy than classic pin-up. Still, I love the green cardigan with the pale blue shirt and matching neck scarf.

The wide striped pants, red socks and brown lace-up shoes make a playful combination. You could borrow just the tied scarf for a more traditional retro outfit.

floral dress and pink accents

If you are looking for lots of floral detail, then this one is for you. There’s pink, pale blue and cream throughout the dark dress, with a pink belt at the waist.

The flowers tucked beside those rolled curls are so pretty. Choose a hair flower that picks up one of the colors in your dress.

floral sleeves and a white scarf

Here’s another floral look, but it’s a little different from the one above. I love the off-the-shoulder neckline and puffed sleeves on this pale printed top.

Read also: 20 Church Appropriate Dresses With Florals, Bows and Pretty Layers

The jeans keep it casual. Add a white headscarf and gold-tone hoops if you want to follow the same combination.

pumpkins and orange plaid

Want a Halloween twist? This outfit goes in a playful alternative direction with a pumpkin top, orange plaid mini skirt and chunky lace-up boots.

The round jack-o’-lantern bag is my favorite part. For a more classic pin-up variation, you could try a longer full skirt while keeping the pumpkin accessories.

gingham skirt and little pins

This is actually one of my favorite skirt combinations here. The full black-and-white gingham skirt looks gorgeous with the plain black top and its wide neckline.

The little yellow flower pin is such a sweet detail. Try adding a small colorful pin to your neckline rather than a necklace.

black jacket and narrow stripes

If you’re looking for a more understated retro-inspired outfit, try this striped high-neck top with cropped black trousers. The black biker jacket and chunky shoes give it a different feel from the dresses above.

I’d keep the dark sunglasses too.

blue overalls and a printed scarf

Don’t want to add heels or a fitted skirt? No problem there!

These blue overalls and the pale sleeveless top give you a casual starting point.

The orange-and-white printed headscarf is the detail I’d borrow. You could tie yours into a bow at the top for a more pin-up-inspired variation.

red gloves and a white wrap

If you want to go all out, this dressy look has plenty to love. The long red gloves match the deep red dress, with a fluffy white wrap sitting around the shoulders.

I am in love with the sculpted waves. The white bead necklace and matching round earrings are lovely finishing touches.

red ties and blue jeans

Last but definitely not least, we have this cute red-and-white combination. The cropped red layer ties over a white top, with blue jeans keeping the outfit casual.

I love how the red shoes match the bow in the hair. Try repeating one bright color in those little details to pull your own look together.

Read also: 20 Outfit Ideas to Dress Like 100 Years Old for a Costume Day