0
Skip to Content
Chelsea J. O'Leary
The Wiley Canning Company Cookbook
Full Looks
Closet
Accessories
Wellness and Beauty
Home
Cabin
Pregnancy and Postpartum
Children
Outdoor
Photography
Travel
Amazon Storefront
About
Wiley Canning Company
The Wiley Canning Company Cookbook
Photography
Select Partners
Print Shop
Substack
Essays and Poetry
Blog
Contact
Chelsea J. O'Leary
The Wiley Canning Company Cookbook
Full Looks
Closet
Accessories
Wellness and Beauty
Home
Cabin
Pregnancy and Postpartum
Children
Outdoor
Photography
Travel
Amazon Storefront
About
Wiley Canning Company
The Wiley Canning Company Cookbook
Photography
Select Partners
Print Shop
Substack
Essays and Poetry
Blog
Contact
Folder: Shop
Back
The Wiley Canning Company Cookbook
Full Looks
Closet
Accessories
Wellness and Beauty
Home
Cabin
Pregnancy and Postpartum
Children
Outdoor
Photography
Travel
Amazon Storefront
About
Wiley Canning Company
Folder: Work
Back
The Wiley Canning Company Cookbook
Photography
Select Partners
Print Shop
Substack
Essays and Poetry
Blog
Contact
No results found
Explore by Category
  • Cabin 5
  • Children 8
  • Closet 11
  • Essays and Poetry 6
  • Home 6
  • Marriage 3
  • Photography 3
  • Pregnancy and Postpartum 9
  • Travel 18
  • Wellness and Beauty 2
On the Go With Happ
Pregnancy and Postpartum Chelsea J. O'Leary 4/17/25 Pregnancy and Postpartum Chelsea J. O'Leary 4/17/25

On the Go With Happ

The experience of motherhood is filled with moments that require not only patience and presence, but also practical solutions that create fluidity in our daily routine.

Read More
On the Go With Doona
Pregnancy and Postpartum Chelsea J. O'Leary 2/6/25 Pregnancy and Postpartum Chelsea J. O'Leary 2/6/25

On the Go With Doona

The physicality of motherhood is inescapable. Each day, I am faced with the importance of being strong, energized, and present as a mother of two sons.

Read More
My Favorite Postpartum Items
Pregnancy and Postpartum, Closet Chelsea J. O'Leary 12/18/24 Pregnancy and Postpartum, Closet Chelsea J. O'Leary 12/18/24

My Favorite Postpartum Items

As we’ve welcomed our second son, it has felt essential to eat healthily, hydrate consistently, and clothe myself in a comfortable, breastfeeding-friendly wardrobe.

Read More
My Favorite Pregnancy Items
Pregnancy and Postpartum, Closet Chelsea J. O'Leary 10/29/24 Pregnancy and Postpartum, Closet Chelsea J. O'Leary 10/29/24

My Favorite Pregnancy Items

Experiencing pregnancy a second time was a tremendous gift. I felt more confident, kind to myself, and certain of my desires and needs.

Read More
Quince Pregnancy Style
Pregnancy and Postpartum, Closet Chelsea J. O'Leary 10/14/24 Pregnancy and Postpartum, Closet Chelsea J. O'Leary 10/14/24

Quince Pregnancy Style

I use Instagram and social media; this is a simple fact. I often ask, “Why do I use Instagram?”

Read More
Bumpsuit Pregnancy Style
Pregnancy and Postpartum, Closet Chelsea J. O'Leary 9/20/24 Pregnancy and Postpartum, Closet Chelsea J. O'Leary 9/20/24

Bumpsuit Pregnancy Style

I am nearing eight months of pregnancy, and I am embracing my bumps, curves, and our baby’s kicks.

Read More
Ilouity Pregnancy Style
Pregnancy and Postpartum, Closet Chelsea J. O'Leary 6/21/24 Pregnancy and Postpartum, Closet Chelsea J. O'Leary 6/21/24

Ilouity Pregnancy Style

Throughout my second pregnancy, I’m having a blast styling my strong, evolving body.

Read More
Sullivan James O'Leary
Pregnancy and Postpartum, Children Chelsea J. O'Leary 12/15/20 Pregnancy and Postpartum, Children Chelsea J. O'Leary 12/15/20

Sullivan James O'Leary

Welcome home, Sullivan James O’Leary. We stand in complete awe.

Read More
A Poem for Pregnancy
Pregnancy and Postpartum Chelsea J. O'Leary 12/1/20 Pregnancy and Postpartum Chelsea J. O'Leary 12/1/20

A Poem for Pregnancy

Poetry attempts to give the obscure and mysterious shape through words.

Read More
I’m putting together my Nashville Rolodex: a collection of the people I trust and the places I go. Over the years, I’ve found myself relying on a small network of businesses, practitioners, and shops that help make daily life feel joyful,
From above… 🏙️💫
Recently, I’ve been thinking about the difference between preserving an identity and allowing it to expand. This second essay in my three-part series explores that tension through motherhood. Though, I suspect it applies equally to aging, marri
Butter yellow (and sunshine!) summer… 🧈🥞🌤️

Photography: @justinrearden 
Location: @blueberry_hill_cabin 
Polo: @buckmason 
Jeans: @buckmason
Sullivan in Central Park… 🌿❤️

Instagram recommends I overlay “Orbiter” by Noah Kahan over these images, which is too much to bear. It’s a must-listen as a parent, if you haven’t yet. 🌔
Rainy days in @buckmason… 🌿 Although I most often work from home, I get dressed in a (comfortable) outfit that inspires me to be energized and present. I loved, and always love, stopping into @buckmason in 12 South to choose a couple of stapl

About:

Follow:

Biography

A Note from Chelsea

Contact

Instagram

Blog

Substack

Wiley News Feed

Shop:

Chelsea’s ShopMy

Chelsea’s Amazon Storefront

Chelsea’s Cookbook

Chelsea’s Full Looks

© Chelsea J. O’Leary 2026 | Terms & Conditions