Cressida v. Chelsy: The Smackdown

28 Oct


Two girls have seriously entered Prince Harry’s heart in the last decade, or at least two girls that the public knows of have seriously entered Prince Harry’s heart in the last decade.   And while any time we speak of Harry loving anyone besides myself, it sends me into a bit of a tizzy (BREATHE, YOU CAN GET THROUGH THIS, etc.), I have squared my shoulders, grabbed a handkerchief and am ready to share my oh-so important thoughts on the pressing matter at hand:

Cressida v. Chelsy

Who is the right girl for Harry?

It’s a battle for the ages, one that includes two beautiful, accomplished girls, and one that ends in the heart of the finest man I do not know.  Without further ado or any more over-the-top adjectives I bring you–

Cressida v. Chelsy: The Smackdown

Coverage starts now.

Round 1: Hair

The royal family is nothing if not a bunch of women with fantastic hair.  Is this an overcompensation for the male pattern baldness gene that plagues their Y chromosome?  Only Freud himself would know.

(The answer is yes.)

Royal Hair Goodness:

Exhibit A:


Exhibit B:

Relaxed Diana - Testino 97 2



So what about Harry’s loves?  Whose hair is up to the task?


Chelsy has the royal hair thing on lock.  You can just see her tresses under an absurd feathered hat as she laughs with Wills and Kate and George, all natural and glossy-like.



Cressida’s hair has more of a bohemian vibe, like, “Hey I just woke up and this is what my hair looks like, suckers.” Also, note the Lauren Conrad braids.


Round 1 Winner: Cressida, though Chelsy’s luscious locks shouldn’t be underestimated.

Round 2: Potential BFF qualities with Kate


Whomever Harry ends up with will have to be Best Friends Forever with Kate, as William and Harry are BFFs, and this is just a rule.

It appears Kate would be easy to share a giggle with, “Haha I love Dirty Dancing, too!”  but the question is not of ease, the question is of kindred soul-dom.


We know that Chelsy attended the royal wedding and has years of double dating and Rock Banding with the Wills and Kate (one can only assume!)  I have to give her a leg up here.  ALSO look at that picture.  That’s some seriously long friendshipping happening.  Does Cressida have a picture with pre-perfect locks Kate?  Exactly.


Cressida seems perfectly lovely, if a bit more daring than Kate, but she simply doesn’t have the history.  I see Kate as the older and wiser sister here, sweetly leading Cressida with the force of her already-iconic example.

Round 2 Winner: Chelsy

Random but important side note:  I know people love to talk about Harry and Pippa and their shared smiles at the wedding and how cute that little happily ever after would be, but hello to the power of blonde, Pippa is not his type.


Glad I got that off my chest.

Round 3: Royal name


Obviously the make or break point in any relationship, whose names match up best?


Princess Chelsy is very modern, like, look, we’re hip to the times, we have a royal Facebook page AND we just allowed women to inherit the throne!  Boom.


Princess Cressida just has a ring to it, doesn’t it?  Regal, really.

Round 3 Winner: Princess Cressida, obviously

Round 4: Love Story

I personally can’t see Harry doing anything awkward at all, in the least, ever ever ever when it comes to dating.  He’s hot.  He’s suave. He doesn’t give a damn what you think about him.  It’s hard to imagine him less than swoon-worthy behavior in the dating world, so we’re going to assume that the details of both love stories are fairly adorable since we do not know them.  Here’s what we do know:


harry chelsy kiss game

Harry and Chelsea met in 2004 and on and offed it until 2010 when they officially split up.  Chelsea is smart (a lawyer!), Zimbabwean (the daughter of a safari farmer!), and is said to have no interest in the royal lifestyle, thus the issues with the lovebirds.  The tabloids love to point out that the two of them continued to hang out long after their split, and that Harry brought Chelsy as his date to the royal wedding in 2011 (aww). (Enough with the parentheses, Jill.)



Cressida and Harry were introduced in 2012 by his cousin Eugenia/aka Owner of THAT royal wedding hat. Cressida is a dancer, student, and the daughter of a  former British “It girl” and businessman.  Really we don’t know much more about her other than she’s bringing scrunchies back.  Thanks, Cressida.

Round 4 Winner: Chelsy 

Round 5: Wardrobe


Chelsy would be the type of princess who wore tailored outfits and black Middleton wedges and fit in oh-so well to royal society.



Cressida would be the type of princess who wore overalls and neon sunglasses, and bucked all royal trends, thus earning her nickname, “The anti-Kate.”  First Princess with duckface selfies is all I’m saying.

Glastonbury Festival 2013 - Day 3

Round 5 Winner: Cressida.  I think we all need a little more overall wearing princesses in our lives.

Overall winner: Chelsy Davey

I know!  The points don’t add up, but you can’t add up points in love.  Chelsy was Harry’s first love, they’ve been on and offing it for years, and I think his torch for her is as bright as Kate and William’s wedding.

Who I think Harry will end up with?  Cressida

Or another fabulous blonde.

Or me.

Probably me.

But definitely not Pippa.

And probably me.

Images: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13

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10 Responses to “Cressida v. Chelsy: The Smackdown”

  1. michaelulinedwards October 28, 2013 at 11:36 am #

    I hear that Harry going to pull another woman off the shelf, someone with a standard name like Ruth.

  2. Linnea October 28, 2013 at 5:57 pm #

    Love it. Especially – “First Princess with duckface selfies is all I’m saying.”

    But wait – don’t ignore that many tabloids report that William had a crush on Cressida’s older half-sister, Isabella! I think there could potentially be some obstacles there to a deep and meaningful friendship between Cressy (no joke, I saw her referred to as Cressy somewhere) and Kate.

    Cressida would be fun just to have a totally different princess style to play up to. Then somedays I could be all together and be like, yeah, I’m just going for a princess look, then the next day when I roll out of bed and throw my hair up in a scrunchie I can still be like, yeah, just going for a princess look.

    • jillianlorraine October 30, 2013 at 11:08 am #

      Linnea, we need to discuss the royals a whole lot more often than we do. Love this and you.

  3. Jeni October 30, 2013 at 10:48 am #

    Sometimes I pretend Jesse is secretly the REAL Prince Harry – he’s also a redhead with tons of freckles. I’m a blonde. It could happen.

    • jillianlorraine October 30, 2013 at 11:05 am #

      This is fully healthy and normal and I support this. I only hope I’m so lucky.

  4. Dee January 17, 2014 at 8:46 pm #

    Ha, what a fun informative read! I’m not a Harry fan so I had no info whatsoever on his girls. So apparently he’s into blondes whose names start with a C. Work on that and you’re gold.

  5. Caroline L. May 7, 2014 at 12:44 pm #

    Found you via Back East Blonde, and I’ll be following you forever and ever and ever now because of this. I too am a Royal Family obsessee (although my heart lies mostly with Kate and not with Harry, but he is tied with George as my second favorite). I try and argue Chelsy v. Cressida all the time with my friends, but no one cares at all. I’m Team Chelsy through and through, and am keeping my fingers crossed now that Harry/Cressida went splitso that a magical, happy, we-were-always-meant-to-be-together reunion is in the works for H and Chelsy!

    • jillianlorraine May 12, 2014 at 4:34 pm #

      Oh my goodness I feel everything about this comment. When the Cressida/Harry split was announced I tried telling everyone it was because of Harry’s lingering feelings for Chelsy, but people weren’t all that interested. I’m holding out, though. CHELSY AND HARRY FOR LIFE.

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