Changing how you dress changes everything

How clothing helped one man navigate challenging times.

Bob Wilson went through a few tough years. He relocated from the West Coast to Massachusetts for a new role with his employer. It’s a great job – Bob is now Director of Strategy & Operations for Information Technology as part of a large F500 healthcare company. But moving is always stressful. More difficult by far was that Bob, a 36-year-old father of two, also went through a divorce during that same period. Finally, and most tragically, he lost both his parents during that same short span of time.

“I mean, really, since 2020, it’s been a marathon of loss and grief, to be honest,” Bob said in an interview with Taelor. “It's really given me a greater, deeper appreciation for mental health,  especially at work, and empathy for my team when they go through events.”

At Taelor we talk about how choosing the right clothes is the key to preparing for the challenges of your week. But Bob shows that dressing well can also be the key to facing the challenges of life itself. 

To understand how that is, Bob walked us through the difficulties of his recent past and how finding Taelor helped him bear the unbearable and enter a new stage of his life.

“My mom was diagnosed with Stage Four pancreatic cancer in July of 2020, and she was still living in California. This was during the full-blown COVID pandemic and she was at that time caregiving for my dad, who had Alzheimer's disease,” Bob said. “So now I had two highly vulnerable parents stuck navigating the healthcare system, with no plan, no wills, no organization of their end of life affairs whatsoever, because none of us plan for that, especially when you're struggling living day to day.”

Bob, like many of us, had a complicated relationship with his parents. But as his parents approached the end of their lives, Bob opted to put aside the complications and embrace his family.

“I decided to help my parents die gracefully. I decided that (would be) my final act of service, my way of showing my parents not just my forgiveness, but my love,” Bob said. 

That involved three trips a week to the hospital for chemotherapy, getting meals set up for delivery, and navigating the myriad challenges of a terminal illness. 

“She fought a really amazing fight for about 10 months and then she got a serious liver infection as a result of one of her surgeries. She was too weak to recover,” he said. “She wanted to go home to die. So I brought her home.” 

Bob’s mother passed away several months later, leaving him bereft. “My mom was my best friend,” he said.

“I had lost my mom and that was devastating. I thought I was processing it at the time. But I was really just very busy,” Bob said. “Sometimes when you're busy, you don't actually take the time to really feel what's happening. And I realized it was like that moment where you're running and you get off the treadmill and it feels like the world is still moving a little bit. The world just kept moving.”

Sometimes the world keeps moving in a direction you don’t want it to. Within months of his Mom’s death, Bob lost his three dogs. “​​One of them had a seizure and died. One of them developed a rare tumor and died two months later. And I feel like the third one just died of old age and grief with the other two dying,” Bob said.

Tragedy seems to build upon itself, spreading in ways that can overwhelm. Shortly thereafter, Bob’s mother-in-law was hit by a car and killed.

From there, things grew even darker for Bob. His father’s Alzheimer's worsened. Bob moved him across the country to the East Coast so they could see more of each other and so that Bob’s two kids could get to know their grandfather. But death came once more. Just 10 months after arriving in Massachusetts, Bob’s father passed away. Still, Bob is grateful for the time they had together. “I got to see the sunset of his life and it was just beautiful and healing and incredible.”

Then, Bob’s marriage ended. He moved from the picket-white-fence home to a small apartment. And Bob realized it was time to rebuild.

A change in clothes and attitude

Rebuilding began with a revelation.

“I started to feel that movement of the treadmill still going forward and I realized I've never invested in myself. I invested in every other person around me,” Bob explained. “I've spent a lot of my life kind of buried in the focus of these other things and people around me, and I didn’t feel great about me.”

So Bob made a decision to focus on something he could change: the way he looked. 

“I decided to pay a little bit more attention to my personal brand and style and to start working on the self-confidence and self-esteem that I neglected while I was in a constant mode of caregiving for other people,” he said.

Bob tried Stitch Fix, but found it lacking. “It took like literally five times for them to get it right. I was putting in my sizes over and over again, getting something sent to me, having to take it back to a FedEx and do this return cycle over and over again on the same single shipment of clothing,” he said.

Eventually he found Taelor, and things began to change for him. He developed a great relationship with his stylist, Melissa Slavick.

“My experience with Taelor was quite the opposite. I got my first shipment and four out of five things fit almost perfectly,” Bob gave Melissa feedback and together, they crafted a look that worked for Bob. 

“The vast majority of stuff is on point. I love clothes that make me look unique and feel unique,” Bob said.

The change in clothes led to a change in how people perceive Bob.

“Last week, one of the people I work with said to me, ‘Bob, you're always smiling and you just seem more confident in the last month than I've ever seen you before and it's just so great seeing you exude happiness,’” Bob said. “And it’s true. I feel better knowing that I Iook better. I never put the time and attention before into figuring out how to dress.”

Bob and Melissa continue to work together. And Bob continues to find growth and comfort in looking better. 

“I have the coolest relationship with Melissa, and it's been entirely virtual,” he said. “And I've gotten to share these little snapshots of what I'm doing. Like I'm going to spread my Dad's ashes, and I want to wear something that looks great in those photos. I'm going on a date for the first time in 13 years. I want to look great for that.”

As his style has developed, Bob’s confidence has grown. He’s trying new activities (JiuJitsu), traveling (Japan and Mexico), and building new relationships. Today, Bob is a different person – a little older, a little wiser, and considerably more enthusiastic about the future. 

“I think what I'm most excited about in this next chapter of my life is the opportunity for personal growth. New experiences, travel with my kids, being motivated to help others through the types of challenges that I just went through,” Bob said. So he’s opening up about what he’s faced and how he has recovered. “I'm focused on being transparent and sharing,” Bob said. “Going through grief and depression is extremely isolating. And it's only through connection that you really can get through that. And it took me a little bit too long to figure that out.”


By Paul Conley