How to Start Dressing Vintage?

(This page may contains affiliate links which are identified by an *. This means that if you make a purchase via one of these links I will make a small commission. Thanks very much for your support in this way, I truly appreciate it. Read my full disclosure.)

How to start dressing vintage is a question I hear so often as if vintage is a mystery that I have somehow unlocked the answers to. I get it, it can seem intimidating when you are surrounding yourself with images of professional pin up models and hairstylist thanks to Instagram and Pinterest. But it’s important to remember, those people ARE PROFESSIONALS. They have dedicated a lot of time and money to getting to the point they are at. If you’re New Year’s Resolution is to take up jogging you’re not going to be running a marathon in February are you?

To try and help I have written this little guide. It is of course based on my experience, your’s may be totally different. But let’s share out top tips and celebrate this amazing sub-culture of ours.

How to Start Dressing Vintage:

1. Work With What You’ve Got

What kind of slow fashion aficionado would I be if I didn’t discourage you from buying things eh? So before you go out and buy anything new, take a look at the clothes, shoes and bags you already own. Do you only own jeans and t-shirts? Do you not have a smart blouse you once bought for a job interview or a cute dress you wore to a friend’s birthday party? The chances are you can start dressing vintage with some modern pieces with a vintage feel and style them to create a ‘vintage’ outfit.

That blouse with a pair of capri pants and some converse trainers could become a cute 1950s rockabilly outfit. With a silk scarf and a midi pencil skirt it can become a smart 1940s look.

Or how about that cute dress? Can you pair it with a little cardigan and some ankle socks for a 1950s teenager vibe?

You see what I mean. You probably already have some options lurking in your wardrobe. Hunt them out, try them on and see what you’ve got.

2. Find Your Vintage

Now you’ve been playing around with clothes you already own, you might have a bit more of an idea as to what styles suit you and the kind of vintage you’re going for. I would say be open minded about this. You might love rockabilly circle skirts and find that once you put them on they do nothing for you. As upsetting as this can be don’t try and force it.

For example, I adore that tall lean 1930s silhouette. I love those bias cut slip dresses and everything about that late Art Deco style. However, I am short and have 40″ hips. In a slip dress I look anything but long and lean, I look short, pear shaped and I feel miserable. And that’s not the point of vintage. What’s so great about the vintage community is that it embraces all body types. When you start dressing vintage you’ll be able to find something that suits you AND makes you feel fabulous.

3. Practice Your Hair and Make-Up

Now we’ve got a feel of what sort of vintage we are going for, let’s move on to the beauty side of things. Hair and make-up can be the most intimidating part of vintage life. Me, I can’t do a cat eye to save my life. I have LOTS of really thick, very stubborn, straight hair which resist curl like nobody’s business. It has taken me a good 3 years to master anything resembling a 1940s brushout and that’s after a week of professional training and making friends with a professional hairstylist.

I started out by mastering a half-up half-down 1940s style do, but with my natural straight hair. Then I mastered a few simple up dos. Once I had learnt to manage and manipulate my natural hair, I moved on to pin curls. I have only graduated onto foam rollers in the past year.

Don’t believe me? All of these styles were done without heat or an overnight set, using only hair pins and clips and took less than 15 mins.

Like I said earlier, don’t expect professional results over night. Practice makes perfect and there is so much you can do with a comb and some hair clips. If you don’t feel like experimenting there are lots of good tutorials out there already for you to follow. Check out my 1940s Hair Pinterest Board for inspiration.

4. Get Ready to Feel Overdressed

Get ready because this is a big one. Once I started really putting an effort into the way I dressed, I felt overdressed everywhere I went. It can make you really self-conscious when you’ve meticulously put together an outfit and styled your hair and but everyone around you is in jeans and trainers. And of course, you look great and people pay you lot’s of compliments but it can add to the embarrassment. You get this feeling of standing out and being conspicuous. But just relax. Remember that the reason you are doing this is because it makes you feel beautiful. Be true to who you are and adopt a ‘haters gunna hate’ attitude and the feeling will pass.

It is also highly likely that strangers will comment on your style, or simple stare at you on the bus. Be polite, but take no crap. I have had people run after me on the tube to ask me where my coat is from, talk about me right in front of me, nudge their friends and point at me. I have also had endless compliments from strangers. A polite smile and thank you is all that’s needed. If they want to stare, let them, you look great. If they are making you uncomfortable stare right back, when they catch your eye the will realise how rude they are being.

5. Start Collecting

By now you are probably rocking your own vintage style, doing your own thing and owning it. Now is the time to start collecting your wardrobe. Why do I say collecting? Because that’s what I think of my vintage clothes as; a collection. Some people collect stamps, some china figurines, I collect clothes. And every good collection represents an investment of both time and money.

Part of the thrill of vintage clothing is wanting something for a really long time, searching everywhere for it and finally coming across it when you least expect it. Sure you can head to a big vintage fair and pick up some amazing vintage pieces, but I love the thrill of the chase.

Charity shops are my hobby. I can’t resist them and I have endless patience for searching through the racks to find a gem of a vintage bargain. The chances of you coming across a genuine 1940s suit are pretty slim these days, but you will find some amazing pieces that can pass as vintage. My case in point is this gem of a dress. Yes it’s from the 1970s but the sleeves, the cut out neck detail; it works. And it’s machine washable. Plus another simple hairstyle giving off vintage vibes. When you start dressing vintage, charity shops are your cheap and cheerful friend. 

1930s Style

6. Make Friends

The vintage world is a great place to be. There are so many beautiful, wonderful supportive people out there who are more than happy to help you out. Engage with them, chat on social media or at vintage fairs and events and get to know some people who share your passion. I’m not saying vintage people are the only people worth knowing, but it’s nice to have someone who can share your excitement when you find vintage shoes that fit.

Most importantly, if you’re thinking of starting to dress vintage, go for it. Take the plunge!

You never know unless you try.

If you have anymore questions or want some other tips and trick leave a comment and I will try to help you out.

Good Luck!

Claude xx