five outfits

1 Girl, 5 Outfits: Carolyn Molloy

I’m launching a new series today that I’m really excited about. Cup of Jo, one of my favorite blogs, has been doing a series for a few years now where they feature women and what they wear during a given week. The series is a great way to get to know women’s style and interests in various cities and industries– and I wanted to do it for the TCP audience, too.

Today, I’m kicking off with my friend Carolyn. (She’s been on here before because we went to the Tony Award Gala together… and Carter took the photos! Funny how things come full circle.) I wanted to start with someone I knew so that I could a) come up with a good system for how to coordinate but also b) gauge interest. Ultimately, I want to feature readers all over the country. Carter and I are heading to DC in November and likely Boston before the end of the year and NYC/NJ/CT always. Feel free to send a nomination in via my contact form if you or a friend are interested in being featured!


Carolyn Molloy, 26

Lives in Hoboken, NJ works in Manhattan as a merchant for a large fashion house

Carolyn Molloy

Hi, I’m Carolyn! I’m 26 and grew up in northern New Jersey. I attended Fairfield University in CT and now live in Hoboken, NJ. It’s a small town with big personality across the river Hudson River from Manhattan. Ever heard of Cake Boss? Yep, that’s Hoboken.

I was lucky enough that my part-time retail job in college turned into a full-time career when I accepted a position as a merchant upon graduation. In the office, I was surrounded by beautiful and incredibly well-dressed people around every corner.

I had my ‘style’ light bulb moment when I realized that what inspired me most about the people I worked with was not that someone was opulently stylish, but that they were perfectly polished, refined and put together. These remain my biggest style objectives every single day. I am so grateful that I am surrounded by people who so greatly influence my personal style and genuinely love fashion as much as I do. I absolutely love my job, I love the people I work with, and I love being a merchant.

When I’m not geeking out on sales reports or upcoming styles at the office, I love to be outside. I grew up skiing, and that continues to be my biggest passion. I try to make a yearly trip out west to ski or hike and enjoy the soulful experience of being in the mountains. Also, being a Jersey girl through and through, I love spending time down the shore. I’m a firm believer that there is no problem a little sunshine, ice cream, and some fancy earrings can’t fix.


How to Style BirkenstocksWearing: Shirt // Shorts (J. Crew, old) // Birkenstocks // Sunglasses

Don’t you love when the hardest decision you make all day is whether to get the burger or the French toast? Sunday was that day. I headed to brunch with a friend at Boulton & Watt and then took a walk down to SoHo for a little shopping. I’ve been very into olive as a transitional color from summer to fall so I paired this button down with my favorite black shorts. They’re oldies but goodies!

To finish the outfit off, I carried this COACH bag which is the perfect size to fit a card case, sunnies, iPhone, gloss and an iPhone charger – all my necessities. And last but not least my beloved Birkies. I might be Birkenstock’s biggest fan. They are so comfortable that I could probably run a marathon in them. Might be the hippie in me but I don’t think they’re that ugly 😉

Looks We Love

Wearing: Black Dress // Shoes // Earrings (J. Crew, old)

I think one of the hardest nights to plan an outfit for is date night. There are many fine lines to navigate around, and the pressure to look your best makes it particularly stressful. Since we had been on a few dates, we decided to go to dinner at my favorite Italian restaurant in the West Village, Malatesta. Shockingly, from the start, I knew I wanted to wear this dress. It’s actually knit so it can easily be dressed up or down and has really romantic off the shoulder and bow sleeve details. I was worried it would be a little dressy for where we were going, but it ended up being perfectly appropriate in the dark, intimate space.

As great as I felt in the dress, the shoes are – without question – my favorite part of this outfit. I bought them as a present to myself for starting a new job, and I am so happy these were what I decided to splurge on. They are so comfortable, and I really feel like a very ‘fancy lady’ when I wear them. My biggest rule for date night… if it makes you feel good – wear it!

Pearl Studded Heels  Outfit IdeasWearing: Olive Top // Jeans (J. Crew, old) // Shoes (J. Crew, old) // Earrings

I scheduled a SoulCycle class in the city Wednesday morning, and I needed to head right to work after class. When I schedule a class, I typically try to pack things that do not wrinkle when they’re stuffed in my gym bag.

I threw together this green sweater with striped trim and my favorite J.Crew jeans. I work in a pretty casual office, so jeans are my go-to. The fit of this sweater is amazing, and the adorable bow in the back & not-too-low v-neck details are perfect. I quickly added some hoops & bangles, and out of SoulCycle I ran…straight to City Bakery for a pretzel croissant and iced latte. ☺

J. Crew Outfit Inspiration    Carolyn Molloy Hoboken

Wearing: Tank (J. Crew, available in some stores) // Jeans // Earrings (J. Crew, old)

I planned a dinner and night out in Hoboken with some friends, so we headed to our unanimously favorite restaurant, The Hoboken Turtle Club. It’s a great little spot founded in 1796 as America’s first social club. Alexander Hamilton and Aaron Burr were some of its first patrons! It has amazing specialty cocktails and a small, but delicious, bar menu. It’s a true crowd pleaser!

I wore this purple eyelet tank that I picked up on sale at J.Crew and a pair of white jeans. I love tops like this for so many reasons, the color, the texture and the cute & flirty fit! Overall winner. I paired it with these gold, beaded ball earrings that I think will become a staple in the colder months. I can see them going great with tartan shirts or a big cozy sweater. After dinner, we headed to meet some more friends at a bar around the corner and start the rest of the night out! (Please note: I may or may not have been banned by the DJ from requesting anymore Justin Bieber songs…just wanted to give the people what they wanted, ya know!?)

Hoboken NJWearing: Polka Dot Top // Jeans //Shoes (Madewell, old) // Earrings (J. Crew, old)

I wore this outfit to work knowing I had plans for the evening. My friends and I had a quick dinner at Souvlaki GR and then headed to 310 Bowery for a fundraising event. If you like good pizza and rosé (& frosé) 310 Bowery is your spot. It’s also beautiful on the inside – think Edison bulbs, exposed brick, reclaimed wood, etc.

I bought this top on a whim, and it is quickly becoming a reliable go-to for work, dates and girls’ night out. It looks great tucked into shorts, with white jeans or a bold red lip! The mixed dot print gives it longevity across seasons and adds a touch of playfulness to any outfit. My friends jokingly call me, “The Girl in the White Tassel Earrings,” because I can’t go a few days without wearing them. So here you go, some white tassels! I can’t help myself; they just go with everything!


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Super excited for this series! I love the idea of seeing how people dress in different industries, and it would also be interesting to see how fashion changes across seasons in different places across the country.

Alex C.

I absolutely love this new style of post! There’s a great mix of pictures and written content, and your friend Carolyn has the most adorable outfits! Looking forward to more posts like these.
Alex C. //

Mary Batsie

You should check out Lexie Lombard’s “What High Schoolers are Really Wearing” series on YouTube! Similar to this idea but puts the spotlight on a younger audience.


oh my gosh– Malatesta is absolutely my favorite restaurant in the city! It deserves its own post!


I love this new series! The short bio and descriptions of each day are so fun to read, too. It’s a nice peek at someone else’s day to day!


Love this! I love seeing that you are so responsive to your readers. I was actually one of your commenters who made this suggestion from Cup of Jo. It’s going to be so great to see the variety of styles featured! Looking forward to more posts! Thanks!
I’ve seen all your tweets–thinking of your family in Tampa. Hope they are in a safe place! Xoxo


Carly, I love this series! Love learning more about other people’s style and a great way to learn about new places in other cities.

Just as a random suggestion, it would be neat to end the post with maybe 5 random facts about the person featured or similar. Talking points could be f.ex. favorite piece of advice, favorite wardrobe staple, etc. 🙂

Cynthia Leaf

Is the “merchant” she works for J. Crew or she just owns a lot of current and old J crew pieces 😉


Love, love, love this idea! I like that the person wearing the outfits writes the post! I guess I’m just super Type A, but I wish it was more organized like Sunday, Monday, Tuesday… 😉 Such cute style and can’t wait to see who is next!


I really like this feature! It’s refreshing to hear a new voice, and her style is so cute! Would love to see you continue this.


Love this idea! As a moderately well-dressed (self-proclaimed, haha) 27 year old Architect living in West Hartford, CT, I would happily volunteer to have you and Carter come explore my world!


Love Hoboken! I’ve lived here for 5 years and hope to eventually raise my family here. I love this idea, keep it up!


This is a great feature! They are all outfits that I would wear and nothing is so insanely expensive that it doesn’t have a wide appeal. She looks wonderful!


Love this idea! I would love to see a few more with women in positions with business casual/smart casual dress codes.


What a great idea! Can’t wait for the posts to come. Does Carolyn work for J.Crew? I love (and used to work for) the company, and found it interesting that almost all her clothing selections were J.Crew!


I love this series. I really hope you get women who work in many many many different fields. Girl power + day to day musings + fashion? YES YES YES!


Ah, this is such a neat idea! I also think the commentor suggestion of 5 random facts would add some fun depth to the piece.


i read cup of jo, too and love this series on both her blog & yours! what i love about hers is how real & approachable the women she features are. i love that their wardrobes are a mix of vintage & current items, high end and lower price point. i also love that they answer questions about their lives, careers, families & overall experiences as women in today’s society. i think this was a great one to start with to gauge reader interest and look forward to unique women & wardrobes you feature in the future! (i’m in Boston if you’re ever looking to do one here!)


I love this idea! I’m so impressed by Carolyn’s amazing earring collection – it’s giving me all of the heart eyes! I can’t wait to see how styles change (or are constant) as you feature readers in different parts of the country 🙂

Biby Chacon

I 100% agree with your Birkenstock’s comment. I grew up in CA where everyone wears them and back them I actually didn’t like them – never really liked any of their style UNTIL I tried them on two years ago! They have so many more styles now and they are so so so comfortable…especially after running a marathon 🙂