Casual, Corporate, Cocktail, 3 Looks, 1 Label with Pilgrim Clothing

I wear many hats, not literally...ok, I lie, I do literally wear loads of different hats because I have a thing for millinery but also I wear many hats metaphorically. Some days I live in active wear, other days I have events, meetings and speaking engagements and then come the weekend I am road tripping down the coast with no shoes on. I've often found my style is hard to define and pinpoint because I have a little bit of everything inside me - tomboy, glam, professional, laid back, vintage, modern, arhhh it drives me mad. I often wish I was just one straight forward thing but for the most part I have come to embrace all of my varying sides. The one thing which is important to me above all else is comfort. This is the key for me whether I dress casually, professionally or for a night out - I never compromise on ease and comfort.

I've found a dress label which caters to all of my different sides - Pilgrim clothing. I've styled 3 completely different looks all from Pilgrim which fit into my life in different ways...


I LOVE this off shoulder print dress. It is fun, on-trend, fresh and Summery. This is my ideal look for a drinks and dinner. Paired with a strappy flat shoe, wicker bag and red lip, this is the weekend dress of my dreams.


Dress: Pilgrim Clothing

Bag: Pip & Co

Shoes: London Rebel

Choker: Etsy

Kerchief: Vintage


I wore this dress recently to a speaking event and it ticked all the boxes. It is comfortable, slightly oversized but perfectly balanced with a shorter hem line at the front, a v cut neckline and a waist tie to bring it all together. A simple heel and cross body bag elevate it up to corporate wear and it is good to go. Effortless, put together and professional.


Dress: Pilgrim Clothing

Bag: Status Anxiety

Shoes: Vintage Peep Toe Shoes


Nothing flatters quite like a t-back style which shows off the shoulders and drops over the waist. This dress is the right amount of skin versus fabric, with the soft drape and overlay over the bust balanced with the tighter silhouette around the hips. The navy blue is gorgeous paired with gold and black details. Again, comfort is key, and this dress hugs in all the right places and flows gently over the rest. I can't wait to wear this dress again, it is fun yet sophisticated and I can't rave enough about it!


Dress: Pilgrim Clothing

Cuff: Witchery


Shoes: London Rebel

To check out these styles and more head over to Pilgrim Clothing!

7 views0 comments

Recent Posts

See All
Kimberley Sara Fashion Stylist

The Style Side is an online destination for fashion, beauty and lifestyle inspiration for women who enjoy style with substance.


Founded by Kimberley Sara, a Canberra based fashion stylist and busy mum, The Style Side is built around a message of empowerment for women - Kimberley aims to inspire women to embrace who they are, pursue what makes them happy, express themselves creatively and be authentic. She believes living a stylish life is about practicing balance, having fun with fashion, staying true to oneself and ultimately celebrating individuality. Her life motto... "be kind and be real, always".


The Style Side is available for a range of E-Styling Services as well as brand collaborations!

Follow The Style Side

  • Instagram
  • Facebook
  • Pinterest
What is your colour season?
Personal Styling

Personal Styling

© 2023 by Ryan Simmons. Proudly created with