As we inch closer to the last week of August, I’m back with a late summer edition of our new series, What I Wore Where. If you missed the previous two, this series celebrates the bags we already own, love, and wear, whether on repeat or for special outings only.
So often, we overlook the bags currently in our collection, giving more love to the ones we’d like to add to our collection next, instead of the bags we already own. Since starting this series earlier this Spring, I’ve challenged myself to rotate my bags even more.
Pulling out bags I haven’t used in months has also led me to have more fun with my outfits and wear things I haven’t worn in a while in an effort to style each bag. From my oldest bag to one of my most worn bags, let’s get into it!
The Ladylike Day Bag
What I wore: Celine Small 16 Bag
Where I went: Lunch meeting at Cafe Zaffri
My Celine 16 bag is one of my collection’s chicest and most ladylike bags. It’s also special to me because I’ve always been a massive fan of Hedi Slimane, and The 16 was his first design for Celine. The bag is semi-structured, and its interior is perfectly designed for maximum organization.
I wear this bag to meetings, dressed up for dinner carried it by the top hand, or dressed down with sneakers and the addition of a logo strap. It’s way more versatile than I first thought.

The Oldie but Goodie
What I wore: Dior Vintage Saddle Pochette
Where I went: Drinks meeting at La Compagnie Flatiron
The bag that started it all for me, my Dior Saddle Pochette, was bought when I was just 13, after saving up for it all summer. It’s one of a few bags I’ll never sell. I don’t use her often, as she’s old and very special to me, but I love taking this bag out for a spin and reveling in the nostalgia. It reminds me that all these years later, I’m right where I belong.

The Pop of Color
What I wore: Loewe Puzzle Hobo
Where I went: Dinner at Lovely Day for a friend’s birthday
When Loewe released a hobo version of its iconic Puzzle bag, I knew this was the Puzzle I wanted after eyeing it for years. I fell further in love when I saw it in Mandarin orange in Portugal.
The color makes it one of my most eye-catching bags, and it’s always a conversation starter with those who know and love bags and those who don’t. In orange, it complements most of my wardrobe, and the size is perfect for daily wear, but not too big to carry to dinner or drinks.

The Favorite Child
What I wore: Prada Cleo Shoulder Bag
Where I went: Sunday aperitivo at Elvis
This series wouldn’t be honest and real if it didn’t include my trusty Prada Cleo, which I wear at least once or twice a week. This series is meant to celebrate the bags we love and truly use, and repetitive or not, the Prada Cleo is that bag for me!

Great collection! You seem to really love and use your bags like the Prada and the Loewe. I like how realistic this collection is and suited to your lifestyle Kaitlin. Personally I’m totally turned off by collections where people have multiple bags in the same style. It just looks like they would never the use they deserve.
Thank you! I truly do! I’ve also gotten to such a good place where I know my style and what I like/will love and use. I no longer hoard and am willing to sell when a bag no longer serves me.
Very Nice!
Late summer bag I’m carrying a Hermes Garden (30) in black or a Loewe bag in orange. Kaitlin you have a great collection of handbags and they suit your style,I have the same bag repeated also. Each person’s handbags are different to their needs. Keep enjoying your collection.
Loewe FTW!! Keep enjoying yours too 🙂
Nice! I love my 16 in small. Mine is a light grey. Your Celine looks more like a gunmetal color which is stunning. I also have the Cleo (black with pastel flowers) and that is such a sweet bag, too!
Cleo with flowers – how pretty!! I still want another Cleo – best bag.
I love this! The idea of shopping my own closet is such a great idea and I need to do it MORE! It’s easy to get caught up in the “what next” of it all and overlook the great bags I already have! Thanks for this reminder and that peek at your STUNNING Loewe hobo—I remember when you first got her! 🧡