Happy ~almost~ new year!!  Hoping your 2018 has been transformative and fulfilling. It’s funny how we wish for a ‘smooth’ year, but those years aren’t the years that push us to grow. Opportunities come up that shift the course of our lives, people cross our paths that change things forever, and all the joys and hardships along the way direct every decision we make. Thank you so much for sending your questions on Instagram – it’s been nice to reminisce on 2018 and share some of my thoughts with you guys. I know how busy all of your lives are, so it means so much to me when you engage and comment on the things I create and post. I know so many of you have been following along for years (love y’all!) but for the newbies, I answered some of these first questions to let you know more about who I am outside of Instagram:

How old are you, where are you from, and where did you go to school:

I’m 27 and from a small town in northern Indiana called Granger. My parents, cousins, and grandma all still live there, so I go back all the time to visit. I went to the University of Kentucky on a cheerleading scholarship (one of the best decisions of my life!) where I majored in fashion merchandising. This was where I initially gained traction on Instagram thanks to all my UK followers and cheerleading fans around the country. After school, I eventually made my way to Chicago where I always wanted to live (it’s only about 1.5 hours from my hometown). After living there for about 2 years, I moved to New York City and I’ve been here for 4 months!

How did you get into blogging:

Right out of school, I worked as a bridal consultant and managed a bridal boutique in Kentucky. I LOVED this job so much, it was so fun working with brides and getting to manage the blog & social for the company. It was a cool way to start instantly working in the fashion industry, while getting a taste of how to run a business.  After that, I worked as a showroom stylist at an interior design firm. This was a dream job for me because I loved decorating + interiors. During this job was when I decided to start blogging. I loved sharing my journey on IG with my friends and family as a college cheerleader, bridal consultant, and interior stylist. I wanted a platform other than Instagram where I could share my outfits, thoughts, and ideas – so that’s when I decided to create a website. Being a gymnast and cheerleader for 20 years – I’d been surrounded by short girls, which was one of the main reasons I wanted to start the fashion side of my blog. I wanted to share outfit tips and inspiration for women under 5’3”, because clothes just DON’T fit us the way they’re supposed to. My family thought I was crazy in the beginning, but I knew this was something I’d love working on, building, and devoting my time to. I always had a vision for how I was going to build it into a career. This quote has always resonated with me “if you want to live a life you’ve never lived, you have to do things you’ve never done”.

How did you grow your blog & gain a following:

I worked my butt off, there really weren’t ever any shortcuts. I worked a full time job and then came home every night to moonlight my blog. I shared my heart, my ideas, and my creativity. I listened to my followers and figured out what they liked & what they didn’t like. I was extremely consistent – posting 4 times/week all year long. I aimed to be relatable through my post ideas and writing, while also tapping into the luxuries of life that make a career in the fashion so enticing. As my career as a blogger developed, I became more and more in love with creating photoshoot ideas that told a story and weren’t just about the clothing or the product. I loved the production side and creating styled images that combined color, emotion, movement, clothing, and beauty. I’m passionate about partnering with brands I believe in and finding ways to capture the attention of their target markets (my followers). At the end of 2017, things clicked when I met my now full-time photographer, Alicia (@aesthetiica). She’s so talented and we instantly became close friends – which gave me my first “co-worker”. She can instantly bring any idea we come up with to life through her photography. Honestly just having someone to be creative with has been the biggest blessing to me. Photography, relatability, consistency, storytelling, and engagement are all key to growing a following.

How do you plan ideas and get inspired for your content?

I wrote a blog post about this, read it here!


My best friend Linds (who I cheered with in college) is from Kentucky and grew up in the same town as Conner. Throughout college she’d occasionally bring him up to me, talk about how cute he was, how he was quarter back at Harvard 🙄- blah, blah. Obviously I was extremely busy dating all the wrong guys at that time, and dating someone two years younger than me sounded like a disaster. Conner and I were both in long term relationships throughout college that lasted until a little over 2 years ago – when we both started over in new cities at the same time. Con in New York & me in Chicago. When Conner found out I was single, he got my number through the grapevine (Linds), and a cute/kinda awkward text eventually popped up on my phone. I was in that miserable stage of dating where you hate everyone and you’re depressed from your last failed relationship, so the thought of going on another date was the last thing I wanted to do.  *But* when I landed in NYC for my first New York Fashion Week, something possessed me to send him a snapchat of the plane landing with some stupid caption that said something like ‘helloooo Manhattan’ AKA ‘hi I’m here, let’s maybe go on a date’. I was in thee most dramatic stage of ‘dating is exhausting and I’m going to die alone’ when this cute Kentucky boy stopped me in my 6 inch heels (but really they were v tall that night bc I knew he was 6’2”) one night while I was in town. I literally remember thinking to myself “HOLYSH*T he’s cute AND normal, what’s happening”. Really-really long story short, Conner and I started developing a long distance relationship and friendship over the course of a year. Fast forward 2 years later, and now we’re both finally together living in New York City!

Long distance relationships:

Can be *very* challenging and is not for everyone. We definitely had our rough patches and times when we didn’t think it was going to work out. Flights are expensive, traveling gets exhausting, and sometimes you just want to be with someone who you can do normal things with – like sit on the couch next to each other and giggle at memes 😏.  My 21 year old self would have never been able to handle a long distance relationship. I was way too needy and unsure of myself back then. I think it’s true for all relationships in general, that you truly need to be so comfortable with yourself and your circumstances that adding someone else to the equation would just be the cherry on top. It’s no surprise that my business was the best it had ever been while we were doing long-distance – because all the time I would’ve been devoting to dating life or hanging out with him – was spent developing myself & my career. It gave me time and space to pursue my blog, travel with friends, see my family, all while slowly figuring out if things could really work out with us. It’s by far the most mature way I’ve ever entered a relationship. We FaceTimed, scheduled trips to see each other when we had free weekends, and made sure to visit each others families together as often as we could (since that’s such a big part of both of our lives). So yes, long distance is hard, but when you truly get along with someone and you are both willing to make it work, it’s possible and honestly can be so healthy for your individual lives. I think the key to making long distance work is having an end goal in sight. Without an end goal or idea of how the distance will officially be over, that’s where things can get really difficult.

On relationships:

Me writing this doesn’t mean I’ve figured it all out or that I’m doing everything perfectly. I have several friends that are still single and a lot who are married with kids. I’ve always been so interested in the dynamics of people’s relationships and what it really takes for a bond between two people to last, so I spend a lot of time talking to the people in my life about what they think really makes a relationship work. The older I get, the more clear things have become for me (and the more I realize my parents were probably right 🙄).

*Personality types matter.

You don’t have to be opposites and you don’t have to be the same, but you have to have complementing personalities that are willing to work together to solve problems and see things from each other’s perspective. If you’re with someone who likes to be constantly going somewhere and doing something, but you’re an introverted home body – that’s probably going to be an issue. If you’re both super passionate about things and have stubborn attitudes, *most* of the time that will create problems (and loud fights). When you’re looking for love, someone who’s personality that complements yours should definitely be on your radar. I can’t tell you how many times I think “wow, he handled my stubborn attitude so well” – and that’s when it hits you that you were with the wrong person before.

*Family life and your upbringing matters.

I’m here to burst your bubble that sometimes love is not enough (my opinion!). After being in relationships in the past with people who’s backgrounds, beliefs, and families were completely different from mine – it just makes things hard 😞. And when it comes to men and women, things are already hard enough. So, my advice to you is to find someone who understands why you are the person you are today. Who loves your family, understands your past, and has very similar values. If things aren’t aligning in your current relationship and it always feels like you’re fighting to make things work, I really want you to take a step back and re-evaluate things.

*Look for someone who’s beliefs and life goals align with yours

Your beliefs form the person you are and pretty much every decision you make.  Humans don’t want to feel alone, which is why we put so much effort into finding a companion.  But when the person you think could be your life long companion’s world view doesn’t align with yours, this can make you feel even more alone. If you both don’t have very strong beliefs about your faith, this won’t be as big of an issue. But, coming from someone who tried to do everything to make a relationship work in the past, really think about this before entering into the relationship.

Breakups & transformations:

Ok – the last little bit about relationships because this is getting so long (if you’re still here, hi 😘). Breakups have been the most transformative life lessons I’ve gone through. They can be SO painful and hard to get through. I’ve had my heart broken to the point where every day I dreaded opening my eyes in the morning. But to be honest, heartbreak has been one of God’s best methods for building my character. I’m so much more resilient, confident, and way less emotional about little things because of the pain I’ve gone through in the past. So if you’re going through it now, take my word for it – you will be fine, you will find someone better, and you will be a better mother/wife/friend because of it.

My faith:

I could write for days about this, so I’m going to dedicated a post to this question within the next couple weeks – so be on the look out 🙂

Moving to New York:

Moving to New York had always been in the back of my mind ever since I started going twice a year for fashion week. Life in Chicago was perfect and I loved everything about it, but I didn’t have ‘my person’ and I was always wondering what it would be like to live in NY. Conner works in Times Square every day and has little flexibility when it comes to travel. So once I felt like we reached the breaking point of almost 2 years of long distance, I knew we had to make a decision. With me being the freelancer and having all of my brand contacts & PR connections in New York, the idea of moving didn’t seem so bad. I knew it would be so beneficial to my career and that we could not keep going on living such separate lives if we were serious about a life together. In September, Conner and I moved in together with one of my best friends – John. We are living in the coolest apartment in lower Manhattan that overlooks the Brooklyn & Manhattan bridge and the last 4 months of NYC life has been so awesome. The career opportunities are endless, the creative industry is so incredible, I have so many friends that live here already, and now I’m here with my two best guy friends. More to come about living in New York (meeting new people, apartment searching, how it compares to Chi).

(pants from Aritzia last year)

Best Career Moments of 2018:

  • Landing my year long long partnership with Tresemme
  • Signing with a management team that’s majorly helped me manage and grow my business
  • Traveling to Portugal & Paris for work
  • Attending the Victoria’s Secret Fashion Show & working with them this year
  • Hiring my first assistant/intern over the summer
  • Partnering with Nike over the summer
  • Speaking on the panel at Create Cultivate Chicago
  • Working with West Elm to design our New York apartment (tour coming this month!)

Best Life Moments of 2018:

  • Finishing decorating my entire Chicago apartment after 2 years!
  • Watching my cousin, best friend from childhood, and best friend from high school become moms!
  • Our 90s house party in Chicago – one of my favorite days of 2018
  • Renting a boat on Lake Michigan for the 4th of July with my family and best friends
  • Moving to New York City in September
  • Having my parents visit Conner and I in New York for the first time
  • Cabo vacation with my family this week!

2019 goals:

Don’t take things too personally. Eat healthier. Create a better work/life balance. Do more things just for fun. Cultivate friendships. Learn how to get around NYC without a gps. Serve others. Ask more questions. Wake up earlier. Cook at home. Read more books. Happy new year!!!! As always, thank you so much for following along

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Showing 19 comments
  • Roxanne

    Love this post, Olivia! I’ve loved watching your success over the year and wish you a happy 2019!

  • Sanya Ivanovic

    You are such an inspiration! I started a blog because I loved following your story in Chicago and wanted to start one of my own. Thank you for being a wonderful role model!

  • Shannon (@popofpippi)

    I love following you and reading your posts – it’s obvious you’re not only beautiful but very smart and capable, too!! I admire you so much!

  • JeriLynn

    I love reading your end of the year posts! Such a wonderful read! <3

  • Tori Friedman

    Thank you for being authentic. I also had a long distance relationship and having an end goal + trust is critical! We’re actually engaged now :). Excited to read about your faith!

  • Taylor

    Several years ago I came across a post on the explore page of instagram of a beautiful family recreating their childhood a Christmas card, as a former cheerleader I began following you ( at the time when your blog was still Lovely Little Style!) For the past five years I have loved reading your posts about health, beauty, and travel. However, my all time favorite posts are the ones like this where you allow us to see inside of your world. It is so refreshing to read genuine and vulnerable posts in a world that is so considered about maintaining perfect appearances. In this post you referenced heartbreak and I will never forget the post you wrote several years ago that shook me to the core. I had also recently had my heart broken and somehow, you managed to put into words exactly how I was feeling in a time when I could not form the words. The quote “Angels”, that you had attached is something that has stuck with me for all of these years. I have been rooting for you this whole time and I am so happy that you have found Conner and are able to reflect on those times as lessons learned. Thank you for being such a wonderful inspiration!

  • Madlyn

    Favorite Blog Post yet!! You are just amazing!!!<3

  • Katrina Jackson

    I have followed you from what feels like the beginning! You have really inspired me and i’m always telling my 13 year old about you. She now follows you. You have had an incredible 2018. I can’t wait to see where 2019 take you!

  • Annaliese

    Absolutely loved this post! Have loved following you for years now. Happy Happy HAPPY 2019!

    xoxo A

  • Jessica

    This is an amazing post Olivia. You are an inspiration, thank you for always keeping life real. Cheers and Happy New Year to you! XOXO

  • Taylor

    Several years ago I was scrolling through my Instagram explore page and came across a beautiful family recreating their childhood Christmas card. As a former cheerleader, I began following you(these were still the Lovely Little Style days)!!

    I have loved following along all of your posts about fashion, health, and beauty. But these posts are by far my favorite. It is so refreshing to see a genuine and vulnerable side of a blogger in a world that is so concerned with maintaining perfect appearances. Several years ago as I was nursing a broken heart, one of your posts shook me to the core. I was blown away that someone several states away could so eloquently put into words exactly how I was feeling. The quote “Angels” that you had posted has stuck with me for all of these years.

    I am thrilled you have found Conner and that you are able to reflect on these times as lessons learned. It gives me hope that I will one day be able to find someone who will be able to complement me so well. Thanks for being such an inspiration!

  • Ashlee

    I loved reading this! I admire your talent and especially appreciated your advice on relationships, thank you for sharing 🙂

  • RxBarbie

    Loved reading this! I want to write my own about me from this. Thank you for sharing.

  • Anastasia

    Thank you for sharing. I love reading your blog. I love that you write in so much detail and share so much advice!

  • Jean Ahn

    Omg thank you for sharing relationship advice! I needed this! I love seeing your amazing content! Happy New Year! xoxo

  • May

    What an amazing post! I love that you talked about your experience in being a blogger and adding personal stories about your relationship. It makes you super relatable!

    May ||

  • Brianna

    I loved this post! It’s so nice to learn more about the blogger behind the blog you read all the time 🙂
    Brianna |

  • Teesha

    Hi, Olivia!
    I absolutely LOVE following you and reading your blog posts. You are the first blogger I ever discovered on IG; creeping just now, I realized it was exactly one year ago from tomorrow (I remember the exact post that brought me to your page lol)!! Your content is always SO interesting and creative, and your style is more similar to mine than any other blogger I’ve found so far. And on top of that, you have the most positive outlook on life and seem so genuine, fun, and sweet! Every time I see a new post from you I feel inspired by you in some way. I just wanted you to know that you are doing an amazing job, so keep up the good work 🙂 Happy 2019!!!

  • Laura

    Hey!! I loved reading this article!! I was just wondering if you would share how you get involved with NYFW and get access to shows. I know certain shoows are for industry members only, but some are public. I’ve always wanted to go, but have found researching the topic difficult…I never seem to look at the right time (too early or too late and everything is sold out). Just hoping you’ll share your knowledge on the topic! Much love! Keep doing what you’re doing!! – Laura

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