Happy Birthday, Princess Charlotte Elizabeth Diana! 
Today four new photos of the princess were released to commemorate her fifth birthday, including this lovely headshot. 
They were taken in April by the Duchess on the Sandringham Estate, where the family helped pack up and deliver food packages for vulnerable people in the local area. More from Rebecca English’s Daily Mail story:
The entire family helped out with a local initiative started by the monarch’s staff, who have been preparing and delivering meals for pensioners and the vulnerable in the area during the lockdown.
Around 1,000 meals were dispensed in the first week alone, and the scheme has been running for five weeks so far.
Back to Rebecca’s story:
This time the Cambridges, all keen cooks, rustled up some home-made pasta which they separated into 12 large bags and tied up with raffia to add to the food parcels. Sources said all the children – even little Louis, two – were involved.
The following day, the family – Charlotte smartly dressed in a black and white checked dress with grey tights and black Mary Jane shoes – then helped to load bags of fresh produce into a van from the Sandringham Visitors’ Centre ready for delivery.
Sources say William, Kate, Charlotte and George spent two and a half hours driving around the area delivering food to those in need.
UPDATE MAY 2: A fifth photo was released today. 
A look back at Charlotte’s fourth birthday pictures, also taken by her mother.
And side by side with her brother’s fifth birthday photo. 
You can really see how she has grown in this montage. 
On Twitter, students from Allington Primary School showed the birthday cards they made for the Princess. 
Thank you, Christin, for the tip on this darling picture!
It has been quite a year for the princess and we have enjoyed seeing her at multiple events. In mid-May, photos of the Cambridge children previewing their mother’s Back to Nature Garden at the Chelsea Flower Show were released. 
The princess takes a turn on the rope swing in the garden. 
Just a few weeks after that, at Trooping the Colour, we saw the children again. Charlotte and Louis looked out at all the activity from the windows of Buckingham Palace before the flypast. 
Perhaps Charlotte gave Louis a lesson in doing the royal wave!
This was the first year all five Cambridges were on the balcony. 
Charlotte looking for the planes. 
And following them as they raced past the palace. 
She seemed to enjoy herself quite a bit during the long, loud celebration. 
July brought a polo match the family attended. In this picture, it looked like Charlotte was pulling her older brother along by a polo mallet.
Kate and the children enjoyed a picnic.
This was one of my favorite photos from the match. 
Another image from the match was released in June by the military as a ‘Happy Birthday’ to Prince George. I love the way Charlotte is looking at Domhnall, the Irish Wolfhound. 
In August the two oldest Cambridge children were out on the water just off the Isle of Wight to watch their parents compete in a sailing regatta. 
A better view of Charlotte. 
When the racing was over George and Charlotte joined their parents just before the awards ceremony. 
You can see the children’s grandmother, Carole Middleotn, on the left. 
Summer faded into fall and Princess Charlotte marked a significant occasion when she started attending ‘big school’ with Prince George.
She was a little shy when the family arrived at Thomas’s Battersea school in West London. (Who wouldn’t be?)
Here she is meeting the head of the Lower School, Helen Haslem. 
The young royals. 
Charlotte’s facial expressions on her big day.
Kensington Palace shared a video of the family arriving at school.
Princess Charlotte arrives for her first day of school at Thomas’s Battersea, joining her older brother Prince George. ✏️📚🏫 pic.twitter.com/8l63WEjzcw
— Kensington Palace (@KensingtonRoyal) September 5, 2019
And later that day they released an official photo of Charlotte and George on the palace steps in their uniforms.
George and Charlotte went to a football match with their parents in October. 
Charlotte is said to have spent much of the match perched on her mother’s knee as Kate explained some of the rules. 
She looked perky in a bright red sweater. 
It was a nice mid-autumn treat to see the family. 
You may remember from the Prince Louis birthday post that in December we saw a black and white photo of the Princess, her brothers, and father that was used for the Cambridge family Christmas card. It was another picture taken by the Duchess. 
We also saw pictures of the family going to and from The Queen’s annual Christmas luncheon.
This is on the way home.
And another view after the party. 
On Christmas Day Charlotte and George walked to church with their parents and other royals. 
Charlotte shaking hands after the service. 
This was the first time either child attended Christmas Day services at St. Mary Magdalene Church on the grounds of the Sandringham estate. 
The family heading off to greet some of the well-wishers eager to see them.
Charlotte and Kate greeting people. 
A mother-daughter hug.
In February, the Duchess recorded her first podcast. In the broadcast, she spoke about a favorite photo.
I’ve got this one photo of Charlotte smelling a bluebell, and really for me it’s moments like that mean so much to me as a parent, and I try everyday to put moments like that in even if they’re small or even if I don’t have time
Here is the photo she was referencing, really a fabulous shot. 
In mid-March, Kensington Palace released a previously unseen photo of Charlotte and George having fun with their parents. The photo was part of a special Mother’s day message the Duke and Duchess shared on social media. 
The photo was by photographer Matt Porteous and appeared to have been shot at the same time the family’s 2018 Christmas card picture was taken.
Later in March, we saw a new video of all three Cambridge children.
To all the doctors, nurses, carers, GPs, pharmacists, volunteers and other NHS staff working tirelessly to help those affected by #COVID19: thank you.#ClapForOurCarers #ClapForNHS pic.twitter.com/XnaUPJyDoX
— Kensington Palace (@KensingtonRoyal) March 26, 2020
They were taking part in their first Clap For Our Carers event, part of a UK-wide effort thanking and supporting those working on the front lines during the coronavirus crisis. 
And we saw the whole family doing Clap For Our Carers just last week, a video of the entire family in front of AnmerHall, their country estate. 
Now for what Princess Charlotte wore in her new pictures, starting with a past-season Zara dress. 
The dress features a houndstooth print, empire waist with ruching, two front buttons, and the distinctive frill, or ruffle, at the shoulders. Thank you to Christine Ross for such a speedy ID of the dress! It looks like the princess was also wearing her standard-style ribbed tights, perhaps from Amaia Kids, possibly this Light Grey pair (£12, about $15 at today’s exchange rates). 
I will look for Charlotte’s shoes later this evening and update the post with any new information.
What a delight it has been to see Princess Charlotte these past five years!
Happy Birthday, Princess Charlotte!
I have a slight feeling Charlottes shoes are from Panache Kids. (panache Mary Jane with heal black patent) they sell from around £50.00. I may be wrong but they look similar!
I love looking at the clothes that royal children wear. It’s obvious their parents can afford well made good quality clothing that is classic and colorful. It also helps that the Duchess of Cambridge knows how to best photograph her children as she always captures their true personalities and knows how to set the scene as far as lighting, props and poses are concerned. I’m so glad I found this site! I think I’ll save the email and have another couple of looks at the beautiful clothing!
A very charming set of photos, especially the full face one, Catherine does take brilliant photos of her three lovely children.
I think the tights are more like the John Lewis cable knit ones, there is defintely a pattern there. https://www.johnlewis.com/john-lewis-partners-girls'-cable-knitted-tights-pack-of-2-navy-grey/p3321296
The dress is also a good choice. In the traditional style Catherine favours but a slightly updated take on it. I think the shoes being patent helps to take a bit of the ‘heaviness’ mentioned above off: it was obviously a bit of a rubbish day (the rainspots on Charlotte’s dress and tights) so cosy tights and solid shoes seems a sensible choice.
I find the shades of colour in Charlotte’s hair fascinating, there is almost a blonde streak on the right side – the door knocking picture.
I’m so glad to see Charlotte in something a little more grown up, she has an air of wisdom about here and I think it suits her. The dark gingham adds a touch of chic for a fabric which back in the olden days used to come in pastel shades. I love the exaggerated floppy collar which has enough sass to take it out of a baby collar and into something a stylish adult might wear at times. Even the raised waist looks less childish. Well done Zara.
I love the grace of her movements, just like both her parents, and the range of expressions Kate captures, from a direct gaze worthy of a professional model, to sweet and pensive as in the fifth shot which came today from Instagram. She is full of character, as are all three children. I thought the grey tights and black shoes a bit heavy looking with the pretty dress, but I can appreciate their practicality. She looks lovely!
The dress is called ‘houndstooth Puritan collar’ by Zara, there are a few places online with photos of the dress without the child model, including:
https://www.newmyroyals.com/2020/05/new-photos-of-princess-charlotte-were.html
NOTE: admin edit
Thank you for the tip on the other dress photo, Em! 🙂
Puritan collat certainly makes sense of the size of that collar. Thanks for update.