The TMI Blog undoubtably features fashion as a way of expression, passion and ideas for all– from seasonal edits, to how-to-wear trends. But there is always a time when I look at my wardrobe for either a regular work day or a special occasion and the dreaded thought bubble blossoms: “I have nothing to wear”. Or, even more recently, how to dress the way I want and feel but in an age-apprporaite way? These are the questions Ready Pretty strives to answer– and has for so many women!

I’ve luckily known Jeannine Adams, Founder and Chief Stylist of Ready Pretty, for several years and is (easily) one my ultimate style icon. A mom, small business owner and a beautiful person, she can do it all! Sitting down with her, I wanted to pick her brain about all things fashion and Ready Pretty.

How is Ready Pretty going? Can you tell us how it all got started?

It’s going great! It has the natural highs and lows of a startup – but all in all, I’m incredibly encouraged and excited about the future.

I’ve had a love of fashion since I can remember – I’ve shared fashion advice, tips and how-to’s in various publications both locally and nationally as a fashion writer, helping women dress better. I’d been helping to style friends and family for year, and then one day realized that I’d created a small base of clients who relied on me to help them get dressed. I decided there was an idea there – and I sat down one weekend and put together a shell of a business plan and came up with the name Ready Pretty at the kitchen table with my husband. Ready Pretty had been born. After that weekend, I was hooked.

What is your favorite part of the business?

Hands down it’s the emails, phone calls and text messages that we receive from our happy users. I’ve always believed that fashion can be transformative – when you’re in a great outfit, you walk a bit taller, pull your shoulders back – it’s an instant confidence boost when something fits right and looks great. When we get those messages from our users, it’s an incredible feeling. We’re in the business helping women feel good about themselves through the clothing they put on everyday. It’s the absolute best part of creating and running this business.

What has been the most challenging?

Positioning ourselves for growth has been a fun challenge to have. We’ve brought on 3 new stylists since we launched, and are hoping to bring in two more before the end of the year. I’m a perfectionist, so ensuring we have the right processes in place to grow as our clientbase grows is important. I so badly want to help as many women as we can, but we want to do it in the smartest and most strategic way so we can scale. It’s a work in progress every day!

What tools do you most rely on for Marketing as a small business?

Hands down, referrals are the number one way that we convert new users. So we’ve used different automated tools to make referrals an easy option for our happiest customers. In addition, social media has been a great way to highlight who we are as a brand, our service and real users in their Ready Pretty picks. Also, good old fashioned networking has proven beneficial for us. Chicago has an incredible startup community and there are so many other young companies interested in collaborations and partnerships that are mutually beneficial. We’ve been able to work with cool brands in Chicago and beyond that have complementary products or services that have helped us to expand awareness of Ready Pretty. It’s also been great to learn from these founders who are in the same place that we are.


What does a typical day look like at RP HQ?

It’s super cliche, but it changes all the time! We’re doubling down on our marketing efforts so we’re in the midsts of several photo and video shoots and further developing our blog to generate fresh and unique content for our users. In addition to that, it’s a mix of corresponding with our users daily, pulling Ready Pretty picks, meetings with local brands and bloggers, pitching ourselves to local media, and laying the foundation for growth. It’s important for us to keep up to date on style and fashion daily, as well as researching new stores, brands and labels – I challenge our stylists weekly to share a new brand with the team to continue to expand our offerings and knowledge to users.

What trends are you most looking forward to wearing for Fall?

I’m not necessarily a “trends” person – I love to wear classics that have an elevated sophistication or twist. That said, I love the textures of Fall. Leather, cozy knits, velvet – it’all so fun to style and wear.


What styles are your customers most looking for?

We’ve seen that our users struggle with workwear as well as what to wear when they have to head out for a special occasion when jeans won’t work, but neither will formal wear. It’s that in between special event, date night or girls night out that our users have a hard time dressing for.

Who is/are your style icon/s?

I’m not sure I have a true style icon – I’m influenced everyday by amazing fashion bloggers, awesome street style, celebrities, etc. That said, Amal Clooney has an incredible ability to look amazing in everything – and her perspective on style is very much in line with mine –  timeless, classic looks with a twist  – she has an impeccable eye for fashion.

What’s next for RP?

Growth! We’re hitting our stride here in Chicago and while want want to continue to grow in our own backyard, it’s also important that we continue to expand nationally. In addition, we’re making improvements to the backend of the website. Soon, users will be able to log in to a dashboard where they can fill out their style profile just once, correspond directly with their stylist, see their Ready Pretty picks and for an additional fee, sign up for our white glove service, where their stylists will handle the ordering process for them, creating one less step to achieving the wardrobe they’ve always wanted.

We’ve got a ton of fun plans in the works, but we’re taking everything one step at a time to ensure the success of the brand.

Want to pick up tips, ask a question about that one piece you cant seem to style right or even get a whole new wardrobe? Head over to Ready Pretty to talk to a stylist today!

Stay stylish,