How To Get Perfect Retro Hair And Makeup Every Time, According To Cherry Dollface

Summer is upon us, which means it’s no longer time to hide under hats and scarves and we can take time making our hair look awesome without having to worry about it getting blown away as soon as we leave the house. It’s also time for cute sundresses and giant sunglasses, which means it’s the perfect time to dress like an old-school pinup model.

The pinup look is the opposite of that effortless, messy cool-girl look, but that doesn’t mean you can’t achieve it for yourself. We love the look, but it can be intimidating, so we chatted with the pinup model, YouTube star, and retro hair expert Cherry Dollface to get some tips on how to rock the pinup look like an old-school cover girl.

How did you get to be an expert at vintage hairstyles?

Cherry Dollface: When I started modeling, there weren’t very many people doing the vintage thing. And youtube didn’t exist yet. So I just used to watch movies and look at photos and sit in front of my mirror until I figured it out!

Do you have a go-to style for every day? If we ran into you on an early morning Starbucks run, would you have Victory Rolls and perfect lipstick?

CD: Haha absolutely not! I work from home so I generally only wear makeup when I film or go out. No use wasting good product! When I am at home I just wear my hair in a topknot and go makeup-free. If I have errands to run or have an average day out, I will probably do faux rolls or side sweep my bangs and do my basic winged liner with lipgloss. I am pretty low maintenance day to day.

Is there an ideal haircut to start with if a person wants to wear retro styles a lot?

CD: There is a vintage style called the middy, which is a very technical cut. But in general, shoulder-length hair cut into layers works well.

You’ve done a lot of looks on your YouTube channel. Do you have a favorite?

CD: I will always love victory rolls of every type.

What is a good style for people with short hair who want to do a pinup look?

CD: Finger waves!!

How do you make a hairstyle last for a really long time, like through several hours of dancing?

CD: Teasing, teasing, and more teasing!! And I always suggest updos for a long night of dancing. Sweat will quickly droop curls.

How did you get started doing YouTube tutorials?

CD: I started modeling in 2005 and had grown a small following. A friend suggested I start a youtube channel as a hobby so I thought it would be fun to show girls how I styled myself for shoots. I had NO idea it was going to become such a big thing.

It’s finally summer! What are your plans?

CD: Traveling!! Touring for half of the summer. Then also hitting some local events. Hopefully, get a weekend or two away with my husband. My tour has been pretty quick-paced. And I am doing a tour of the midwest right now–I am teaching pinup hair and makeup classes and organizing pinup photoshoots. I also have west coast and south/east coast tours coming up!

Check out more videos at Cherry Dollface’s YouTube channel and Facebook page for more class and tour information.

(Photo: Facebook/Lauren Horwood Photography via Cherry Dollface)