five outfits

1 Girl, 5 Outfits: Shana Jordan

Today’s post is another installment of 1 Girl, 5 Outfits! Shana and I went to Georgetown together, and I was actually her TA for one semester of Entrepreneurship (my favorite class!). I’ve always been impressed with her and our paths have crossed post-graduation as well. During a recent email exchange, I asked if she would want to be featured in the series and she said yes! I love how she has found her personal style as a working girl in NYC.

Shana Jordan

“Style is something we already have, we just have to find it”- DVF

Hi! I’m Shana Jordan – a 27-year-old living and working in Manhattan. I currently work as a brand manager for Time Inc.’s lifestyle brands, but I got my first start out of school working at ShopStyle, a fashion start-up. Outside of the office, I am a self-proclaimed foodie (you can follow along here), who loves exploring new restaurants, experimenting with new culinary experiences and hosting dinner parties at my apartment.

Despite my fashion background, it took me a long time to find my style. After 13 years at an all-girls school (nine of which were spent in a uniform!) and four years at Georgetown, I arrived in New York with a wardrobe that consisted of J. Crew staples and vibrant dresses. Needless to say, when I first came to the Concrete Jungle, a city that counts navy as a pop of color, I struggled to adjust my preppy style to my new urban surroundings. My time at ShopStyle opened my eyes to a whole new side of fashion, showing me that there was room for both leather and seersucker in my closet. Now, I like to say that my style marries preppy with urban chic.

ShopStyle served as the springboard for developing my personal style, but after four years there, switching to my current job presented me with the opportunity to re-establish my own personal look, which brings me to the five outfits that I am sharing today. I hope you enjoy a glimpse into my everyday wardrobe:

NYCSimilar Shirt // Jeans // Boots //  Similar Earring // Necklace // Similar Clutch

My first two looks are what I would consider “desk to dinner.” Being in media, I have
the opportunity to both dress up and dress down depending on what the day holds. Although I am more comfortable being slightly more dressed up, like in the second look, I have come to have a new appreciation for jeans after realizing they don’t have to feel too casual. This look here is probably one of my favorites and truly reflects my newfound style balance. The ties on the sleeves and the printed snakeskin bag elevate the outfit, while the blue jeans and booties still keep me comfortable enough to run from meetings to cocktails. This look fits into any occasion and is a constant staple in my rotation.

I am a true believer in the importance of having a few go-to LBDs. To me, the LBD is something you can easily dress up or down because it always makes you feel comfortable.

What to wear working in NYC

Work to Date Night Shoes

Bag (Rented) // Dress // Flats // Heels // Similar Necklace // Earrings

In New York. the “shoe swap” is a consistent part of my day, which is why you see both the flats and heels in this picture. I learned quickly that strutting around New York Carrie-Bradshaw-style does a number on your shoes. I generally commute in flats and then switch into heels before going into meetings or heading into a restaurant for a date night with my boyfriend, Ian.

Prepster 1 Girl 5 Outfits

NYC Outfit

What to wear in NYC

Met Similar Jacket // Shirt (rented) // Jeans // Similar Shoes // Rag and Bone Tote // Similar Necklace

All black is something that I would never have worn before moving to New York, but the more years I spend here, the more black infiltrates my closet. New York has made me realize the simplicity of a good pair of black jeans and go-to pumps. The pattern on my shoes and the orange in the bag soften the harshness of a fully monochromatic look. Using pops of color is a playful way of bringing a touch of prep to my more city look. This look is perfect for a Friday night, meeting up with friends for dinner or drinks.

Work Outfit Inspiration

Dress (Rented) // Jean Jacket // Shoes // Gold Necklace // Pendant Necklace

I am lucky to have the best group of girlfriends a girl could ask for – someone is always down to try a new restaurant or meet up for coffee or a glass of wine to debrief on what’s going on in our lives. We all have our own fashion sense, so it’s with them that I typically either fully embrace my preppy style or try out a piece that is a little out of my comfort zone. Leopard is my go-to print and my favorite way to add a little personality to a classic look.

Workout Outfit

Workout Outfit Inspiration

Bag // Sneakers // Pants // Similar Top (original Talbots Factory)

Thank goodness for athleisure. Every weekend, weather depending, Ian and I try to start our day with a few laps around the Central Park basin. From there, we often run errands or grab breakfast at a new local spot. It’s so nice to be able to do this without having to go home and change.

* Rented pieces are part of my Rent The Runway unlimited subscription, which I can’t
say enough good things about. I was first attracted to Rent the Runway unlimited because it allowed me to experiment with incorporating rented pieces into my existing staples. Renting allows me to have a revolving closet that keeps it feeling like I always have something new.

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I love this series so much! She is so stunning and put-together! Please keep these coming!

Alex C.

Shana, I love that you mentioned that you talked about how you’re slowly embracing black, because that’s something that I’m discovering while living in France for a few months! All of your looks are adorable and practical, and it seems like you’ve got city living down pat. Carly, I love this series and hope you keep it up!
Alex C. //


I spy a deer ring 😉 I still wear mine too. So fun to see you up here, Shana!


Shana, I am so extremely delighted, and even overjoyed, to read your excellent discourse, detailed and finessed, pertaining to the evolution of your individual fashionstyle sense. Your descriptions and explanations contain total clarity and much thoughtfulness of this entire concept. The photos are beautiful, as are you, Shana. You radiate a particular luminosity, and your intelligence and sweet nature are evidenced by your penetrating gaze, dazzling smile, and positive body language. Congratulations, you’ve produced a really valuable aid to address merging chic and preppy fashion styles with simplicity and significance. I love you, Shana Jordan!