Iconic Winona Ryder Looks From 3 Classic Movie Roles

The best of Winona’s looks come from some of her most immortal and timeless of films, and they make the perfect inspiration for Halloween.

I’m not sure which came first: people comparing me to Winona Ryder or my deep and unwavering love for her.

I’ve been getting a pretty constant stream of Winona comparisons since early tweendom, when puberty left me with cheekbones and a pouty disposition instead of the boobs I’d been promised. It’s OK, though, because I truly and endlessly adore Winona.

She and I have a lot in common, besides our standard-issue pixie-esque bone structures. We both totally used to shoplift and date Johnny Depp. Except she was stealing Marc Jacobs thermals and I was stealing dollar-store scrunchies, and by date, I mean she was engaged to him and I wrote him fan mail when I was 12. Also, Marci thinks he might be my dad. Moving on.

Winona is an extremely talented and gorgeous screen icon I have always and will always love. One of the best things about Winona is how well many of her onscreen roles translate to real-life beauty inspiration.

Which of us born between Gen X and Y didn’t seriously consider a pixie cut after watching Winona elucidate so well our depressive pangs in Girl, Interrupted? And who among us wasn’t a lonely and awkward tween expanding our headband collection after watching Winona as the Catholic-wannabe, desperately longing daughter of Cher in Mermaids? And none of us can pretend we didn’t at least momentarily envy her effortless short-haired and laid-back look as she channeled postgrad malaise in Reality Bites.

Surely, none of us have been entirely immune to the Winona Effect. She is a true goddess among women. I miss her. Where are you, Winona?

But the best of Winona’s looks come from some of her most immortal and timeless of films, and they make the perfect inspiration for Halloween. And since I’ve yet to write an article here on xoVain without receiving at least one Winona comparison, I’m finally giving in and going for it. Let’s do this. Free Winona (looks) once and for all!

Look 1: Kim Boggs from Edward Scissorhands (1990)

God, I love this movie. If you have an awesome man friend, or an awesome any kind of friend, who will be the Edward to your Kim, I can guarantee you an awesome Halloween.

Kim is a beautiful, young cheerleader who starts the movie dating this total douche, but after her mom takes in the sad, albeit freaky as hell, Edward, she grows as a person as she falls in love with ol’ Ed even though she knows their love could never be. So sad and beautiful.

Kim’s look is angelic. With her long, blonde hair and glowy complexion, she looks every bit the prom queen. As a dark-haired and glowering ogre, I’m not sure I can pull this off, but let’s try.

I started with Diorskin Nude BB Crème for a soft, sheer coverage and a bit of glow. I used Benefit High Beam to highlight, sweeping it lightly across the tops of my cheekbones and right over my brows and then blending with a big fluffy brush.

When filling in my brows, I used a light brown color and treaded lightly, so as to keep them from contrasting with my soon-to-be blonde hair.

I wanted to keep my eyes somewhat natural, but still add lightness and shimmer. I applied Rimmel London’s Scandal Eyes Eyeshadow Stick in Witness White all over my lids, and then went over it with the pale peach shimmer shade from Tarte’s NeutralEYES Volume II Natural Eyes Palette. The white underneath helped the peach to pop a bit instead of blending into my skin.

Using a small angled brush, I worked a thin line of dark brown shadow from the same palette into my lash line and then went over my lashes with Rimmel London Volume Accelerator Mascara.

I swept some CoverGirl Classic Color Blush in “Soft Mink” across the apples of my cheeks, then gently brushed e.l.f. Studio High Definition Powder all over my face.

I ordered my wig off of Amazon for about $15. Rather than using a wig cap, I put my hair in a low pony, which I then pinned up against my head. I pinned back all my bangs and wispy bits with small pins.

After putting the wig on, I trimmed the bangs a bit so they wouldn’t poke my eyes, and adjusted it until it felt right. I cut off a bit from the layers in the back, and stuck them inside the front of the wig, right above my ears, to hide the visible bits of brown peaking through and to give myself some little face framing pieces.

For my lips, I used a small amount of ModelCo Party Proof Lipstick in Disco Fever, a soft pinkish-coral that’s one of the prettiest shades I’ve ever worn.

If you can’t find a replica of any of her outfits from the film, wear a simple, light colored dress or top.

Look 2: Veronica Sawyer in Heathers (1988)

This is one of the most quotable films of all time, and one of the best-looking, too. While I saw it when I was really young, it wasn’t until I watched it again in college that I truly understood what a remarkable and insane movie Heathers is. I mean, can you imagine if this movie had come out in 2013? It wouldn’t! The heroes of the movie are MURDERERS and nobody gets in trouble! Christian Slater’s character brings a gun to school and doesn’t get even get suspended.

Whoa, this movie was ahead of its time, and thank goodness, because it would not have happened in our time. But this film is PERFECT. It is, indeed, so very.

And the styles are really fun to recreate. The Heathers themselves, all clad in full '80s color-coded gear, make a super-awesome group costume, as do Veronica and J.D.

Winona in this movie is such a joy to behold. With her angsty diary writing, monocle and homicidal inclinations, she brings quirk to another level.

Veronica’s wardrobe in this film leaves you PLENTY of options for apparel. I went with a look somewhat similar to the ensemble she rocked at the gas station and subsequent frat party where she vommed. Lick it up, baby!

Let’s start with hair. If your hair isn’t naturally curly, curl it all over with a medium-size iron or hot rollers. Then comb your fingers through all the curls to turn them into big waves. Using a fine-toothed comb, tease the whole situation for some volume.

Curl your bangs under with a big round brush and don’t bother trying to flatten them down. You don’t have bangs yet? Ugh, such a pillowcase.

I then used Benefit’s The POREfessional topped with Revlon PhotoReady Powder for a smooth matte finish, like the popular girl I am.

Then I heavy-handedly brushed L’Oreal True Match Blush in "Spiced Plum" from the middle of my cheekbones up to my hairline.

Winona’s makeup in this film isn’t so over-the-top, but this is Halloween, ya know? The film’s costumes are not only great-looking but intentional. Each character dons her own color scheme. Veronica wears blue, but as the film goes on, she fades more into blacks and grays as the plot darkens.

But I like blue, so let’s do it. The extreme always seems to make an impression. I covered my lids in Maybelline Color Tattoo 24HR Cream Gel Shadow in Edgy Emerald, which is very pretty but reads more blue than green on my skin. Blue, like drain cleaner! Pretty.

Then I worked the same shadow in Electric Blue into the crease and outer corners of my lids, and blended inwards. Try not to let it get beyond the lid. Popular girls are nothing if not precise. Chaos is what killed the dinosaurs, darling.

I worked some black kohl liner into my lash line as well.

Then I applied Sephora Collection Cream Lip Stain in Always Red.

I applied some gloss over the stain, because nowadays I use my grand IQ to decide what color lip gloss to wear in the morning and how to hit three keggers before curfew.

Then I blew up the high school.

Look 3: Lydia Deetz in Beetlejuice (1988)

OK, I have a confession: I’ve never seen Beetlejuice.

I mean, I’ve seen parts of it on TV or in passing, but it’s always been a film that’s such a part of our American collective conscious that I just never figured I really had to watch it. Like Star Wars or Indiana Jones. (Don’t hate me. I’m extremely busy, and always have been. Since birth.)

But then I cut my bangs on the internet, and people were like “Lydia Deeeeetz! Tuuuuutorial!” And, must oblige.

So I watched Beetlejuice. Twice. And I REALLY LIKED IT. A LOT. PROMISE! But I’m not gonna say his name a third time…

Let’s get down to Lydia. Her look has become iconic. There are SO many Lydia Deetz makeup and costume tutorials out there, it’s intimidating. Luckily, I am not afraid of anything. Except for spiders and the future.

I had planned to do a Lydia tutorial in her standard look, but then our lovely friends at Refinery 29 came out with such a good one, I decided to go in a different direction.

Because Lydia’s wedding look is obviously WAY more fun! I’m so glad to have seen it so that when I hear the phrase “Red Wedding,” my mind can produce imagery other than the life-ruining hour of television Game of Thrones already gave me.

The first step to Lydia’s look is her ghostly, goth girl pale skin.

Dear readers, here is how much I love you. Not only did I watch this movie for you, I risked my life for you. Well, maybe not. But here’s a word from the (un)wise.

To achieve this pale and sallow complexion, I purchased some white face paint from my nearest drugstore. “Perfect!” I thought. While I’ve used and loved MAC’s white face foundation Alle used in her Morticia Addams look, it wasn’t really in my budget, and I hate spending money on things I won’t use often. (Exhibit A: Please see my wardrobe full of fur coats at my house in Mississippi. I need to move.)

So, I got home and started applying this face paint. It was gross and sticky, but I persevered. For you. Then, suddenly, my face started feeling really warm. Then hotter and hotter. Then itchy ALL OVER. It was like a ghost was possessing my face, but instead of forcing me to dance to a delightful Harry Belafonte tune, it was scorching my face with red hot itchy bumps. I rushed to the sink and splashed cold water on my face for approximately 30 minutes.

So let that be a lesson to all of you out there attempting makeup looks on a budget. Use your brain and do a patch test first.

So then I waited a few days and cried the whole time because I’m not smart or interesting and my skin is sort of all I have going for me, OK? Leave it alone. It’s showtime.

To get the actual look I ended up with, I used very pale foundation. Then I covered my whole face very, very heavily with Maybelline FIT Me Pressed Powder in the lightest shade of that as well. I used the small puff that came with the powder, and then a big fluffy kabuki brush to blend it all together. But don’t blend it into your skin! You want to be ghostly white, duh.

Then I used a large shadow brush to sweep a dark matte brown shadow all over and around my eyes. I worked the shadow all the way down into the bags under my eyes and up to my brows.

Then I used a combination of blush and a matte red shadow to cover my lids and all the way out to my hairline, as well as a bit under my eyes for good measure. Matching your eyeshadow to your dress is MOST stylish when your dress is red, duh. You could also use lipstick for this, if you wanted.

That’s it for makeup on this look. If you wanted to, you could add mascara or eyeliner, but I didn’t find it necessary. Actually, I forgot. I was still reeling from my incident a few days prior, OK? Life is hard.

Now, hair. I combed my bangs into my face and then pieced them into small sections with my fingers. I worked gel into each piece and twisted them at the ends.

Then I took most of my hair, and teased it hard. After backcombing it into a huge pile atop my head, I pinned it randomly to keep it in place before spraying it out of its mind. I left some hair down on the sides and in the back.

The costume for this look is definitely the trickiest part. I found a vintage red prom dress at the thrift store for $10, and then I bought a yard of red lace on sale at the fabric store. I simply tucked in the lace along the top of the dress and pinned it to the sleeves. Then I bobby-pinned several long pieces of lace onto the back of my head for a makeshift veil.

It turned out pretty well. I miss my black hair.

This look works great on its own, or if you go with a partner dressed as Beetlejuice. SHOOT. I SAID IT AGAIN.

I really like the promo shot of Lydia holding a baby doll, so here.

These looks were really fun to create, and it gave me more reasons to think and talk about my main woman, Winona, which I always appreciate.

Would you use any of these looks for Halloween? What’s your favorite Winona look? Do you still think I look like her? Wino Forever <3