Welcome to Saturday fashion lovers! Today, I would like to introduce you  to one of my very best dressed friends. Just kidding, she’s one of my best friends too, BUT she is also very well dressed. Her name is Jessy, she is a preschool teacher in Massachusetts and one of the most loyal, loving and positive people I have been ever so blessed to know. I asked her to be a part of my style sessions and she didn’t think twice to help out.

Let me tell you a little about this girl; not only is she a pretty face, but she has a knack for fashion. She models (check Instagram for more on her interactions with American Eagle and my personal favorite – Kate Spade!) Stay tuned because she is dipping her feet into opening her own online boutique. I’ve seen some shots of her ideas and I can guarantee you that I will own pretty much all of it.


So, Jessy and I got to talking. I asked her why she loves fashion (as I am always interested in why people gravitate towards fashion!) and she said “I love fashion because it’s a way of expressing yourself without having to say anything at all. That, to me, is really powerful.” If she had to describe her style in one word it would be feminine, although she finds that confining her style to one word is extremely difficult. She gushes, “Fashion means a lot to me. It’s a form of art! It’s a way to express my personality and feelings, and it’s a great way of connect with people all over the world.”

As many know, fall is my favorite season of the year when it comes to fashion. I love the colors, scarves, chunky sweaters and lattes. Jessy agrees, stating that there is something about a good flannel, scarf and knee-high boots really makes her happy. Not to mention it’s the perfect outfit to frolic around an apple orchard with your best gal pals – for those of you who follow me on instagram, I’m sure you have seen our apple orchard pictures! Now you see where those comes from!


“I feel most comfortable in a good pair of skinny jeans. It’s a good starting base and you can easily dress them up or down! It makes creating an outfit so simple. My go to piece,  hands-down, would be a slouchy oversize sweater. I have a section in my closet just for them. I love to style them by getting them just a little too big so they hang off my shoulder, I just can’t resist sweater weather season. What influences you? The season, the atmosphere? Jessy related, saying that her surroundings inspire her style. She loves traveling, and while growing up with her mom, it was made a point to always say yes to exploring. You only get one life, take advantage of being with friends and going to new places.


Now, I’ve known Jessy for a few years now, and I can tell you she has a real obsession with peacoats. She said “I can thank London for that, as well as I have a hankering for a killer pair of heels – thanks to watching the women in Paris strut on the streets.” She likes to try new trends IF they still make her feel like herself. It’s always fun to switch it up.


Now lets talk about shopping! Personally, I love to shop – in fact, I purchased some new sweaters from Loft just today. Jessy can normally be found shopping at the beginning of each season. What would she be looking for? “Anything neutral in tone catches my eye when shopping” Clothes, purses and shoes? You name it!”  Often times, as women, we have our few main stores that we always hit up for new trends and styles each season. She loves Anthropologie. Anything that looks romantic and girly – she gravitates to!

When it comes to brands one of my all-time loves is Kate spade – she eagerly agrees! Not only is it one of her favorite brands but it’s also one of her dream modeling jobs that she landed this past year. “Their look is timeless with just a touch of fun! If I could swim in the sea of all their purses I would!”


Style Icon? “I don’t have just one fashion icon but Lauren Conrad comes to mind at the moment. I adore her sense of style and her looks are timeless and classic,  while still being current.”

I always end each of my style sessions with random questions – for my own fun – Diamonds or Pearls? “Diamonds are a girls best friend right?” (always a great answer!) As I’ve mentioned before, I am really tall – I asked Jessy if there was any struggle to dress herself because of her height. She indulged me by expaining that she is 5’8 – so clothes usually fit pretty well. The only area she really needs to pay attention to is her legs because they’re long, so when buying dresses, you need to find a modest length.

Okay – shoot, give me a fun fact! “A fun fact about me, not related to fashion, is that I love sharks! I can watch marathons after marathons of shark week past and present for hours. Ever since I saw Josh when I was seven I’ve been hooked!”

Stay tuned for next weeks style session, featuring Emmalyn Anderson – @emmalynbonnie

xoxo – Style by Leanne

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