I LOVE this outfit. I really haven’t had many excuses to get dressed up since 2020…. I know other people have been back in the office and back to doing fun things, I’ve just felt like I’m on this pandemic, pregnant, postpartum, mom-of-a-toddler hamster wheel for three years. I think I forgot what it is like to socialize and to have plans that require something other than a pair of jeans. (I have had lots of plans but most involve motherhood and chasing around a toddler!) It’s left me feeling a little lost, honestly. I swear I’ve spent the last year trying to come to terms with my new body shape and reevaluating my personal style.

Well, again, I love this outfit. It felt like me and I felt like me and isn’t that one of the best feelings?! I wore it in the city last week. It took me from a fun fashion event in the morning to a meeting in the afternoon.

J. Crew sent me this dress and I absolutely can’t get over how cute it is. It’s a little short for an office setting, but it looks so cute layered with a shirt. Could definitely wear with no shirt too, if the weather allowed. But turtlenecks, little blazers, a cardigan. You can style this in so many ways.

Fits slightly big, I think. I am wearing the smaller of my two sizes and it fits perfectly– including my chest. (If you’re smaller chested definitely size down at least one size I would say.)

The pleats are darling and it feels like such a classic– yet modern- dress.

Highly recommend 🤗

Also I get DMs about the Gucci bag. Honestly, I think I prefer it more than my Chanel? My Chanel has more sentimental value to me and, don’t get me wrong, I am obsessed with it. But I definitely think the Gucci Jackie bag is something I reach for more. I bring it out for almost every date night. It fits all the essentials– including my Kindle 😉.

Dress (c/o) // Similar Blouse // Handbag // Shoes (under $60!)


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Hi Carly, I like the silhouette of the dress, and would be interested in suggestions on where to wear it! It feels too short for the workplace but too business-like for a social event. Thanks!


Hi Sarah,
I read your comment and immediately thought of a solution. You could add a colorful or festive cardigan over it and some fun tights or stockings and chunkier shoes like loafers or mary janes to give it a more social event edge. I would be too cold to have bare legs in winter since it is quite short!


This whole outfit is so perfectly Carly-The-College-Prepster and I love it! You look so comfortable and confident! 💜💜


Carly, you wear this dress beautifully and look graceful.

In college and my early twenties I wore a number of dresses similar to this style, but being 34 I cannot pull it off anymore. I don’t know exactly why but I genuinely think my face simply looks a little too old and the dress-style makes me look like I’m even older than I am.

A huge part of your personal style that I appreciate and value is that your face, hair and personality really match the clothing. These pieces suit you because you still look gorgeous and full of youth.