How to Start Dressing Retro

Recently, I’ve had quite a few people ask me, how can they start dressing vintage or pinup? What items should they start purchasing? Where should they go? and what to avoid. Instead of repeating myself like my childhood parrot, I thought I might turn this into a blog and hopefully help more people on their vintage journey.

How to start?

It’s best to figure out what your personal style and preferences are. Some people are really comfortable wearing tight and sexy outfits whilst others prefer more loose and comfortable clothing pieces. Each to their own; dressing vintage has no real rules. It’s a great way to learn to express yourself and who you are and also to embrace your personality. Pinup gives you the chance to combine era’s and styles so you can go for something more sexy like a fitted dress, but perhaps make it cute with a sweet cupcake print? Or perhaps you’d like to dress more flow-ey with a swing skirt but incorporate darker elements such as spiders or something witchy. The possibilities are endless. Try surfing Instagram to find pinups and fashionistas you admire and look at how they dress for inspiration. Pull out your favourite elements and try to make them your own. Remember to be yourself!

Pinup clothing has a few iconic symbols and prints which are a great base for a beginners wardrobe. They can all be easily mixed and matched and compliment many basic clothing items. As you start to add to your wardrobe, you can gravitate towards certain colours you like and add your own flare as you get comfortable.


  • Red
  • White
  • Black


  • Leopard
  • Cherries
  • Sailor Motif’s
  • Floral


  • Gingham
  • Polkadot
  • Stripes
  • Plaid/Tartan

Bottom Coverings; When starting to wear vintage, separates are a great place to start as it allows you to mix and match different tops to different bottoms and give you more outfits per item of clothing. As a challenge, try to put away your jeans for 10 days; this will make you really start to think and plan your clothing choices and help you stay within the vintage style. You can always add your jeans back into your styling if you pair them with perhaps a cute cardigan or blouse.

Skirts; To get started, find a good quality midi (or knee-length) skirt in a plain colour. Black is always a good choice as you can pair it with lots of different things.  The skirt can be flared/swing or pencil/wiggle. Skirts are a great start to any vintage wardrobe as long as they are of an appropriate length. If you’re not sure what length suits you, buy something a bit longer and bring up the hem little by little until you find where the skirt flatters you.

Capri; As well as skirts, a pair of good Capri pants/pedal pushers is also a great way to get started. Sometimes taking away someone’s jeans is really confronting so Capri’s are a great way to ease the transition. You can find Capri’s in a range of different colours and they will soon become you’re ‘go to’ as they are really comfortable to wear.

Cardigan; Cardigans have to be one of my favourite pinup items and I own way too many! Get yourself a couple of good quality coloured cardigans when you start your vintage wardrobe; there are so many styles, cuts and colours to choose from that I’m sure you’ll find something you like. They can be worn over dresses and tops, tucked into a belt or over the top of your outfit; you can also accessories them with collar/cardigan clips and fun brooches.

Blouse/Top; To get started into wearing vintage, you don’t need to get yourself an expensive blouse. Even just going to Kmart or Target and picking up a plain long or capped sleeve shirt can help you along your way and some stores also sell really cute vintage t-shirts. Tops can be worn tucked into skirts and pants, cinched in with a belt and you’re ready! They don’t need a lot of work and if you get a staple colour, you’ll find they are easily paired with things you may already own. If you’re after a blouse, a wide neckline, cute collar and buttons are all things that give you a vintage feel. Don’t go for anything too see-through and keep the top relatively simple.

Dresses; Ah yes, dresses, my old friends. Most of my wardrobe is dresses because I find them comfortable, easy to style and they always look classy and elegant. If you wish to start wearing dresses, I’d recommend finding your local retro/pinup store and trying on a few different styles. We all have different body shapes and we should dress to flatter our bodies; by having a shop assistant help us, we can be pleasantly surprised which styles we can pull off. This also gives you the chance to try things such as petticoats and mixing up colours. If a dress really sings to you, go for it!

Scarf; One of the hardest things to learn when dressing vintage is hair styling, but don’t worry, I have a solution for you; a hair scarf! It’s easy enough to pinup a simple red bandana and you can then just wear your hair in a ponytail and add the bandana as a headband. You can also give yourself a loose back bun, and wrap the scarf around your head covering your bun. If you can master a front roll you’ve got some extra brownie points. A scarf can also be tied around your neck for a super cute look or around your head for a more classy feel.

Red lipstick; If you are feeling brave enough, put on some red lipstick. You don’t need to wear heaps of makeup to achieve the vintage look, sometimes just some red lipstick will tie your look together. If you aren’t comfortable with red lipstick, try a lip tint to add some colour.

Ballet Flats; You don’t need heels to wear vintage, some cute and simple ballet flats can be perfect to complete your outfit.

I’ve created a few capsule looks below to get your started. Each separate can me worn with other pieces as the colours all work together. All items were sourced from Gwynnies Emporium and Collectif Clothing.


Remember to always be true to yourself.

As you evolve yourself, stick with things you really like. For example, I love floral prints and have a lot of it in my wardrobe; I find it pretty and it makes me feel good, but it might now work for someone else. If you decide repro-vintage isn’t for you, start looking around for true vintage. Mix true vintage with repro if that makes you feel good. If you don’t feel comfortable in leopard print, don’t wear it; you need to be comfortable and discover who you are.

Find your own personal style and embrace it.

You don’t need expensive clothes to be a pinup and a vintage wardrobe can be achieved on a budget. Shop around, look at sales and ‘swap pages’ on Facebook; talk to other people about their wardrobes and see what they think about certain things. If you like darker spookier things, great! If you love tiki and tropical, great! If you need your jeans but want a fun top, great! Wearing vintage is also about being comfortable with who you are. When you wear vintage, you do stand out on the street; it can give you a sense of confidence and inspire others to dress differently too. As long as it makes you happy, do it. If it doesn’t make you happy then don’t do it and try something else; perhaps find a local community of like-minded people and be inspired by them!

Do it your own way but most of all, have fun!

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