WAGS Work: Tiffany Whoolery

WAGS Work: Tiffany Whoolery

The WAGS Work Series aims to show our readers that we are more than the stereotypes you might be familiar with—we’re creative, hard-working, driven, and willing to do whatever it takes to make this lifestyle work. We also hope to inspire women in all walks of life to get creative and think outside the box when it comes to working and creating the lives of their dreams. Please reach out to the women featured in this series if you have questions or want to learn more about what they do.


Tell us who you are, how you got into the baseball world, and a little bit about you and your fiance.

My name is Tiffany Whoolery and my fiance is Nick Ramirez, a LHP in the Milwaukee Brewers Organization. Nick and I met at Spring Training in Scottsdale, Arizona in March of 2016. We met through mutual friends at Bottled Blonde and honestly just stayed friends for quite awhile. We would text here and there, but I really didn't think we would ever end up dating because he was from California and I'm from Texas. Finally after months of endless phone calls and texting all day, we set a date for me to come see him in Biloxi, Mississippi where he was playing double A ball.

I honestly knew I loved him before I even went to go see him. His birthday is August 1st and I was running around Nashville with my best friend, Karalyne, scrambling to overnight him Lululemon clothes before we ever even hung out one-on-one. This sounds dumb, but I knew how much he meant to me when I was taking time out of our trip to make him feel special from states away.

So two weeks after his birthday it was finally time to see him. There had been hurricanes in the gulf coast so it took me 14 hours to get to him. I-10 was closed and my car had a total meltdown in Houston causing an additional 3 hour delay, but I was determined to see him. I ended up staying there for 5 days and having the best time of my life.

I was so sad to leave and after only being back in Austin for 2 days,  I asked him if I was crazy if I drove back. He told me to get in the car, so I did! Honestly, like they say, the rest is history! A year later he proposed and now we’re getting married in less than three months!


Tell us all about your job, what do you do, and how long you’ve been werkin’ it.

So I actually have two jobs. My first job, that I guess you could say is my 8-5, is as an accountant for a manufacturing company. I’m in a niche market and it’s a very small company that heavily relies on me and has done so for the last four years, so they really had no choice but to let me travel or I was going to leave that job.

The reason I was going to be able to leave this job is because my second form of income is working as a Senior Stylist for Stitch Fix, which is what this post is geared to! I have worked here for a year and it’s amazing!


How in the world did you find this job?

Fashion has always been a huge passion of mine, but I never thought I could make a career out of it. I had seen commercials for Stitch Fix and had a lot of people tell me that I should apply when they opened up a hub in Austin, so I did!



Was working remotely just part of the job, or did you have to ask for that?

I was pretty lucky with my main job and got to tell them I was traveling. This isn’t the case for everyone and I know asking your job to convert your position into a remote one can be tricky.

Luckily, with Stitch Fix, everything is done remotely. The only time you ever go to the office is for your interview and your one day of training. That’s it! From then on out you’re on your laptop and working from the comfort of your own bed (if you’re like me anyway)!


How do you balance your work and living the baseball life?

Stitch Fix is time consuming, but you can work as little as 15 hours a week. It’s also up to you how fast you style. I’m required to style a minimum number of people a week and I can usually style them faster than the hours scheduled. I recommend knocking your hours out early so that you have the rest of the day to yourself. Or heck, I’ve even taken my laptop to the games and styled people in the stands! Just make sure your wifi is strong enough.


How did finding this job impact your life personally, and for the two of you?

Nick and I are in the middle of planning a wedding, which can be extremely pricy. This job has helped pay for just about everything with the wedding that my family isn’t covering and it’s been a true blessing. It will be nice once the wedding is over and all my extra income can go into savings or if baseball throws us a curveball, we still have my income to get us through.

It also feels nice to contribute and it gives me something to do. Baseball can be lonely sometimes when they’re on a road trip and you’re not with them. So instead of binging Netflix all day, I get to have fun, feel productive and make money! Talk about a win!


What’s a typical workday like for you in the season? In the off-season?

During the season I wake up at 9 am and start styling right away. It’s pretty nice to be able to work with your PJs on. Nick wakes up around 10:30, so once he’s up I stop styling. We spend time together and eat breakfast and then he’s off to the field by 1:00. Once I get back home I continuing styling.

I usually work Monday thru Friday for about 3 hours each day. So it’s really not a huge chunk of my day. While doing this I also juggle my other job and basically go back and forth with what I’m working on.

During the off-season it’s pretty much the same, but I actually go into the office at my accounting job from 9-6. I can usually squeeze in styling while I'm there because I am an extremely efficient worker.


What advice do you have for other WAGs who are looking for remote work or trying to work up the courage to ASK to go remote?

I highly recommend Stitch Fix. If anyone is interested, I would love to give the referral link to those of you that are in a hub city. You’ll just need to visit Stitch Fix Careers online and see what cities they are currently hiring in.

If you’re going to ask your current job to allow you to travel, I recommend to be realistic and know your worth. Show your company how you can offer the same value and work ethic while being away from the office. I even thought about offering a pay cut at my accounting job, but luckily it didn’t come to that.



What’s been the HARDEST part so far? What’s been the BEST?

The hardest part of about Stitch Fix is when you get negative feedback from a client. My job is to make women feel amazing in their outfits and when I fail to do that, I take it personally. Other than that, I really can’t say there are any negatives.

The best part is that it’s remote. You have meetings once a month with your lead but it’s via video chat for about 45 minutes. Another great part is that I get to look at cute clothes all day and style fun outfits with women I have connected with who trust me to make them feel and look good.


What’s one thing you wish EVERYONE knew about being a WAG/baseball life?

I wish people knew what a grind WAGs or anyone in the baseball world goes through. This life isn’t all that glamorous. Baseball can come with financial struggles, career uncertainty, and a number of other stressful things. We as girlfriends, fiancees, and wives have to be strong support systems for our men and sometimes that means contributing monetarily.

I think a lot of people on the outside looking in think we’re all just posh girls letting our men provide for us when that’s not the case. We have dreams and career goals as well, but while we’re in the baseball world, we alter our dreams for the time being.


Where can we find you online / how can we keep up with you?

To keep up with me or if you’re interested in hearing more about Stitch Fix you can visit my website at www.TiffanyWhoolery.com or by following me on Instagram: @Tiffanywhoolery!


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