interview

Feeling Confident In Your Personal Style With Jenny Eversole

November 21, 2022

Thank you to Basecamp for sponsoring this episode.

Reading Time: 6 minutes

Streamline Your Style: How to Create a Time-Saving Capsule Wardrobe with Jenny Eversole

Some people are just so… fashionable, aren’t they? I’ve always envied people who look put-together and always seem have the cutest clothes. Turns out feeling good in your clothes doesn’t have to take a lot of time or money.

How to set boundaries

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How would you describe your style?

Is it “Whatever I was wearing yesterday” or “The first thing I grabbed out of my closet this morning”? If so, you’re not alone.

But I also know that you probably want more style, and to feel more confident with your clothes. While I’m not saying we all have to look like a million bucks all the time, I am saying that there’s so much confidence from feeling good.

Plus, as a time management coach, I can absolutely tell you that having clothes you love will cut down on all that time you spend rifling through your closet shouting, “I have nothing to wear!”

A while back, I was on a journey to feel more polished and professional, but I was at a loss with what to wear. So… I scheduled a virtual styling appointment at Style Space — and I was blown away, y’all.

I loved the whole team, and after connecting with the cofounder, I just knew I had to have her on the podcast. So, without further ado, let’s meet Jenny!

Meet Jenny Eversole

Jenny Eversole is living the expat dream! With her three kids, this American-Canadian and her husband have moved to Germany while running their online business, taking full advantage of the wonders of remote work. 

With a full-time business and full-time mom life, Jenny’s made a habit to craft a solid schedule that allows her to get everything done in a day, no matter how crazy! Between her morning work shift, the afternoon mom time, and her second evening shift in her business, Jenny’s truly cracked the code to balancing it all on her own terms. 

Where it all began

At 28, Jenny was a fashion designer who realized there was a gap in the fashion design industry. As a lover of clothes, she’d taken for granted her ability to easily decide on a wardrobe or outfit. So many people struggle with this, and as most of us know, what we wear can almost make or break our self-confidence sometimes. 

After having her twins, Jenny was getting ready for her first T.V. appearance since her pregnancy, and had no idea what to wear. She was terrified she’d make the wrong choice. We all know that clothes are about so much more than your appearance — they can translate to people’s opinion of you, your opinion of yourself, how you feel, and more. 

She called her sister, a stylist, and they put together an outfit that Jenny felt amazing in. Her confidence was boosted, and she absolutely rocked the interview! 

We’re not born with the skill to know exactly how to style ourselves, just like we’re not born with time-management skills. So if you don’t have time (or just don’t want to) learn all the secrets to styling, give yourself permission to outsource that! 

How does Jenny do everything? 

Jenny’s a big believer that you “can’t have everything by doing everything.” She’s become an expert at prioritizing and time-blocking her day. Family time is solely for family, and work time is solely for work. This highly focused environment allows her to accomplish so much in such little time. 

And of course, a shared family calendar is her best friend when it comes to organizing! She also loves Calendly for booking calls with clients, as it integrates with Google Calendar and easily lets her block off times she is and isn’t available. 

Balancing a global team 

With so many team members across multiple time zones, Jenny’s become a master at balancing her needs, as well as the needs of her team, when it comes to work and boundaries. 

Each Tuesday, they have a team huddle to check-in and manage their current projects. They use Slack for quick communication whenever they need. 

Project management

With a launch happening every 2 weeks, project management and clear work requirements is a must for the team. They use Jira to manage their projects easily. 

Additionally, knowing the management styles of her team members is very important. Understanding how people want to be managed makes it so much easier to create a cohesive team. 

She’s up front about her own working and management style, and values everyone working together as a team, without a hierarchy. 

One of the best tools her and the team use are The Four Tendencies by Gretchen Rubin to understand their different personalities and how their minds work. 

I love Jenny’s take on time management, and her and Style Space are actually hosting a Time Management Week the week of November 21st, 2022. Visit their Instagram account @stylespace.official to hear about capsule wardrobes, simplifying your mornings, and more.

Making the stylish transition

Style Space is actually Jenny’s fourth career… and she’s only in her thirties! She loves transitioning out of work whenever she feels like she’s hit a plateau, and pursuing something new, different, and challenging. 

When she and her husband started Style Space, they knew from the start that they wanted to hire people who had strengths that they didn’t.

So, what is Style Space? It’s a virtual styling company that allows you to receive expert advice on building or adding to your wardrobe from a dedicated stylist. 

How to build style confidence

Style Space actually has a quiz you can take to help you define the right style not just for your taste, but for your body type as well. For example, some people carry more weight on their top than bottom, and so their ideal style highlights their legs. 

When working with a Style Space stylist, you’ll have someone to lean on to define your body type, colors, and the styles that would be most flattering. 

You have power over how you present yourself and your image. Style is such a powerful tool of expression, and when you truly view it that way, things WILL shift in your life. 

As Jenny points out, whether you like your clothes or not, you have to wear them everyday. So why not get clothes that you absolutely love?

Remember that we’re always changing

Everyone always says that the one constant in life is change. And that’s no different for our bodies and style! Jenny uses the 80/20 rule when it comes to closets: if you notice you’re only wearing 20% of your closet 80% of the time… it’s probably time for a change! 

At the same time, it’s important to have one or two staple pieces for all occasions. When I had my virtual styling appointment with Lauren, from Style Space, I told her that I felt like I was spending all my time in athleisure. But when it came time to wear something a bit nicer, I had no idea what to put on! 

Cool and trendy without the try-hard

It’s so easy to get sucked into the ever-changing trends and rotating our wardrobe on a near constant basis. But you don’t actually need to stay up on all the trends! If something does grab you, Jenny thinks it’s great to pick up a staple piece. However, it’s more important to have investment pieces that will last you through years. 

And of course, wear what you feel comfortable and confident in!

Creating your dream capsule wardrobe

A capsule wardrobe essentially means you own staple pieces that you can keep in your closet from year to year. They likely won’t go out of style, and are completely interchangeable. This way, you can get a lot of variety with fewer items. 

If you’re thinking of creating a capsule wardrobe or just expanding your closet, I definitely encourage you to have a virtual styling session with a member of Jenny’s team

But if you’re looking to create a capsule wardrobe on your own, Jenny’s go-to tool is Pinterest. Find your body shape and color palette, and then type into Pinterest: [body shape] + [color] + capsule wardrobe. 

I’m so happy I got the chance to chat with Jenny about Style Space and all things wardrobe confidence! I’d love to know — what was your biggest takeaway from our conversation? Tell me in the comments! 

In this episode, we talk about: 

  • The confidence that comes with style
  • How Jenny balances full-time mom-ing with full-time styling
  • Accounting for the 80/20 rule when it comes to your closet
  • How to create a capsule wardrobe

Resources Mentioned In This Episode

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