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The winter months are closing in, and it’s time to rethink your clothing choices. As much as we love cute skirts and little strapped tops, they just won’t cut it anymore.

However, just because the weather’s getting colder, doesn’t mean your pin-up dresses need to be retired to the back of your wardrobe. There are tons of ways to work them into winter outfits. In this article, we’ll give you all the details.

If you’re getting ready for a Christmas party or just looking for some everyday looks, we’ll help you put together an outfit that turns heads as well as keeping you warm. With our winter pin-up wardrobe essentials, you can’t go wrong.

Read on to find out how to wear a pin-up dress in the winter.

11 Ways to Get a Winter Pin-Up Dress Look

Not sure how to make your pin-up dress work with winter clothes? You don’t have to compromise your style by covering yourself up under endless bulky layers. Here’s how to stay stylish and make pin-up clothes work when it’s cold.

1. Accessories

No pin-up look is truly complete without accessories, and when it’s cold, there are so many more that you can wear! The colder it gets, the more you can add to your outfit.

An accessory can change your entire outfit. Hats and scarves are fairly basic choices for keeping warm while looking cool, but there are so many more to choose from.

Here’s a list of just some of the accessories you can rock with a pin-up dress.

  • Headscarves
  • Headbands
  • Turbans
  • Clinch belts
  • Satchels
  • Purses
  • Shrugs
  • Shawls
  • Hats (like berets, bowlers, pillboxes, and panamas)
  • Vintage earrings

Whether it’s a cute headband, a leatherette clutch, or some sparkly costume jewellery, it can make a statement that completes your outfit. Mix and match them and you can create lots of different looks with just one dress.

For some inspiration, see our post on retro accessories you can’t live without.

2. Hosiery

Hosiery is great for adding a subtle extra layer to protect your legs from the winter chill. Not only that, but it can totally amp up the style of your outfit, too!

That’s if you choose some snazzy options like seamed pantyhose or fashion tights that have funky patterns on them. These aren’t your only options, though.

There’s also over-the-knee socks, thigh-high socks, compression stockings, and stockings with suspenders. If you like, you can combine them with extra undergarments like camisoles, corsets, or lace slips so you have an entire layer of clothing under your pin-up dress.

The amount of warmth you get will depend on the denier of the hosiery you wear. The higher the denier, the thicker they’ll be. Check the number before you buy!

3. Leggings

As the winter months draw nearer and the weather gets colder, you might feel as though it’s too chilly to wear a short pin-up dress, even with tights. That’s not the case. All you need to do is layer up!

Leggings can be worn under any type of skirt or dress, allowing you to show off those pins while keeping warm. The best thing is, they come in hundreds of different colors, patterns, and styles, so you can get really creative with combinations.

If you’re still worried about being cold, don’t worry. There are even thermal leggings available to keep your legs nice and toasty. Who needs trousers?

4. A Petticoat

Petticoats are a pin-up girl’s best friend. They not only add shape on volume to your dress, but they also provide a hidden layer of warmth that functions like a secret blanket.

What more could you want in a winter outfit?

While tight pencil skirts and mini skirts are great for the summer months, wearing them during the winter could leave you shivering. Plus, they don’t allow for a lot of movement. Lots of women love the delightful feeling of swishing around in a twirly dress, and a petticoat gives you an excuse to do just that.

While many people think that wearing a petticoat makes you look big and frumpy, they are actually very flattering. This is because by expanding outwards, they make your waist look smaller. This is part of the reason why women began wearing them in the 1800’s.

There’s no arguing the fact that wearing a petticoat just makes you feel more elegant.

It has to match the length of your skirt, though. Otherwise, the bottom of your skirt will hang loosely off the bottom. It’s not a good look.

If a petticoat isn’t part of your normal wardrobe, you might be a little confused as to how to wear one. The elastic waistband should sit on your waist, not on the hips. If it doesn’t line up with your skirt, you can always adjust it and pin it to your bra or slip to keep it in place.

If you want some extra va-va-voom, you can even layer up a couple of petticoats on top of each other. Just don’t go overboard and use too many. We love petticoats as much as the next gal, but if you’re overly enthusiastic about them, you might end up looking like a meringue!

5. Long Sleeves

A pin-up dress doesn’t have to be sleeveless or bandeau. In fact, there are plenty of styles that give you a little more coverage. Ones with long sleeves are great for providing extra warmth in the winter.

Half, three-quarter of full-length sleeves give a dress a touch of vintage chic. Plus, they stop you from getting goosebumps when it’s breezy. For something a little more 70’s, go for a dress with flared or frilled sleeves.

If you don’t have any these at home, try our long-sleeved polka dot party dress or knee-length plaid pin-up dress on for size. These styles are a great place to start.

6. Knitwear

There’s nothing like the comfort of a warm sweater or cardigan when it’s chilly.

Using knitwear means you can still wear your floral, flowing summer dresses when it’s cold, too. Throwing a sweater over a short-sleeved number makes it work in the winter. It also provides more depth to your outfit for a more interesting look.

Whether you prefer snug turtlenecks or plunging v-necks, you can work a sweater into your get up. If you don’t want to cover up too much of your beautiful dress, opt for a shrug sweater. It will keep your arms and shoulders warm while allowing you to show off the rest of your outfit.

Cardigans are great, too. Waist-length cardigans go particularly well with swing dresses or skirts. They compliment the shape nicely by nipping your waist in while the skirt flows outwards.

Another great thing about cardigans is that you can personalize them by adding funky lapel pins. The enamel pin trend has grown to huge proportions in the last year or so, and there’s an endless variety of designs out there. These pins go hand in hand with pin-up looks.

Now, you can say just about anything you want with a pin. Strong political statement? Got it.

Feminist mantra? No problem.

A kitten riding a unicorn over a rainbow? You can have that, too.

7. Gloves

One of the things that made pin-up idol Marilyn Monroe’s look so iconic was her signature gloves. Sometimes velvet, sometimes glittering with sequins, usually scrunched at the elbow, they always gave her that come-hither look that no one could resist.

If we could, we’d wear gloves like these all-year-round, but sweaty, clammy hands aren’t ideal. That’s why when winter comes around, we get excited to replicate the seductress look by adding gloves to our pin-up outfits.

You can do that, too. Wear long gloves that reach up to the elbow for a sophisticated, elegant look or shorter lace gloves for something more vintage. Even leather driving gloves can be paired with a pin-up dress.

Black or white gloves look great, but bright colours like red or green can be matched with other accessories to create a more striking look. Get creative with them!

8. Faux Fur

Winter means you can go full pin-up by jazzing up your outfits with some fabulous faux fur add-ons.

Faux fur fashion is always on trend. It adds a touch of glamour to your look that no other fabric can achieve, and since its manufacture doesn’t harm any animals, it’s even better than the real thing.

You can try leopard print styles for classic chic, or go for the ice queen look with stunning white faux fur.

If the idea of wearing a full fur coat is a little too outlandish for you, don’t worry. Faux-fur trimmed coats, hats, gloves, and scarves will do the trick, too. If those don’t tickle your fancy, try faux fur earmuffs, shawls or wraps. These little touches can make all the difference.

9. Boots

Boots are absolutely essential for a winter outfit. Luckily, they can be matched perfectly with a pin-up dress, too.

That’s because there are so many different types to choose from. You can mix it up with ankle boots or knee-high boots with platforms, high heels, kitten heels, or Cuban heels.

If the idea of boots gives you visions of sore and achy, feet, don’t worry. Walking in boots doesn’t have to be a pain. If you prefer, you could just go with completely flat ones. They’re more comfortable and they look great, too!

10. An Umbrella

Getting caught in the rain can completely dampen your look, making you go from fab to drab in a matter of minutes. If you keep an umbrella with you, you can stay dry and stay fly!

You don’t have to carry around a boring old umbrella that doesn’t go with your outfit, though. There are plenty of vintage-style umbrellas out there that match a pin-up dress perfectly. Think Mary Poppins.

Wooden handles, ruffled edges, polka dots and floral patterns are all signs of classic umbrellas. Choose one of these and you don’t have to compromise your style to keep dry.

11. Coats

The idea of covering up your beautiful pin-up dress with a coat might not sound ideal, but if you choose the right one, you can still look effortlessly gorgeous.

Try a rockabilly trench coat, a long wool coat, an over-sized duffle coat, or even a leather biker jacket. Of course, sheepskin and suede are good winter choices, too.

All of these types of coats can look great over vintage dresses. All you have to do is get the combination right.

If you’re wearing a puffier pin-up dress with lots of volume, go for a shorter coat. Something that comes to the waist would be best. If you’re going for something a little more subtle, you can layer a longer coat over the top.

Tweed and plaid coats work best with dresses with block colours. Mixing too many patterns in one outfit will look busy and could clash completely. In that same vein, if you’re wearing a polka dot or striped pin-up dress, you’re better off choosing a plain coat to go over the top.

You can always just keep it simple. For classic pin-up winter looks, black or red coats work best.

As well as style, colour, and material, you also need to think about shape. To accentuate an hourglass figure, choose a coat which has a wrap around waist. If you can’t find one, you can always add a waist belt over the top.

The Finishing Touch

Once you’ve put your outfit together with your pin-up dress, you’re not done. You still need to work out how to make the whole look pop with the right hair and makeup.

Picking out the styles you want is one thing, but creating them from scratch is another. Unless you’re lucky enough to have your own personal makeup artist or hairdresser, you’ll have to learn how to do them yourself.

We can help you out in that department, too.

With our tutorials, you can learn how to create the perfect pin-up look. See our posts on how to do pin-up hairstyles and vintage makeup for step-by-step guides.

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