How I Answered the Nagging Question: ‘What Should I Wear Today?’

Updated: Feb 17, 2020

Over the last 15 years, I can recall hundreds if not thousands of times when I or someone I know needed outfit advice. Whether I was hesitant in a fitting room buying clothing or at home in front of my mirror putting together cute outfits, the emotional indecision and uncertainty over buying clothes or choosing an outfit for a date night were real. Here are two common scenarios I struggled with when I was unable to get the honest outfit advice I desperately wanted.

While getting dressed for an important occasion, I’d stand in front of the mirror and ask myself the same nagging questions, How Do I look? Can you wear brown shoes with black pants? Whether it was a night out, first date, concert, birthday party or job interview, it was vital to me that I felt confident in my outfit. However, 85% of the time I felt unsure, indecisive, and most of all anxiety when all I needed was a little outfit inspo! So, I’d change out of the clothes in question and reach for my go-to uniform and style, removing any indecision because it required zero thought. It was moments like these that I always craved outfit advice from others.

There are so many fashion traps out there that I’d fall into with clothes during my early and mid-twenties. I’d find myself shopping online for clothes and buying clothes I didn’t wear, need, and sometimes wish I’d never bought. Or I’d spend hours browsing clothes without buying anything because I wasn’t able to make a confident decision. Honestly, I went crazy with regret because I wasted A LOT of money and time. I began to realize that if I could get outfit advice during these what to wear to an interview? and should I wear white to a wedding? moments of indecision, I’d save money, closet space, and time.

Two surprised or shocked women in the pop art style

After my epiphany, I started analyzing the most significant issues I had with clothes. I was spending too much money, time and negative energy on buying clothing and deciding what to wear. I didn’t want clothes to alter my mood for the worst. Instead, I wanted buying and wearing clothes to be easy and make me feel like the truest, most confident version of myself. Sounds logical, right?

I spent years talking to my sister about the idea of creating a fashion app for personal style, and an opportunity came knocking in my life. In 2016, I received an offer to join STYL as a co-founder to help create a community of people who provide honest but kind outfit advice that helps us make confident decisions. So, today we endeavor to do just that with STYL. We're not perfect, and we're always listening and learning too, which is what I love about building this friendly neighborhood. We've all needed fashion tips; I like the idea we're there together, building something new and sharing our thoughts, opinions, and questions along the way, so that we can all dress confidently, together.

- Krissy Lloyd, Co-Founder