Resetting Your Style: Questions to Help You Along the Journey

If you've read my post on the Stages of Your Style Journey, then you're familiar with the Fashion Royal. You're someone who's gone through a lot of the fashion stages already, like finding your body type or discovering your color season. Some of it's worked for you, some of it hasn't, and you felt good about it for a long time.

But recently, something has changed. Whether you're going through a major life change, your body has changed, or something else, the old standbys don't work as well as they used to. Your outfit that used to make you feel 100% confident now inspires little more than a shrug.

Maybe you've gone back to the internet, trying to find that missing piece that will make you feel like yourself again. That might even be how you ended up here. If that's you, I'm sorry, but you won't find an easy buying guide here.

Instead, I created a list of four questions I want you to answer. Most of them are based on my own experience being where you are right now. Take a look at these questions, think about them, journal about them, and don't worry if the answers don't come to you immediately. Be patient, and trust that inspiration will strike when you least expect it.

1) Look to Your Past Self- What were you wearing? How did it make you feel? Was there a time in your life when you felt creative, free, and excited? Do you remember what you were wearing?

I'm asking you these questions not because I think you should recreate the exact thing you used to wear. If you want to, go for it, but keep in mind what served you then might not serve you now. The real reason I ask this question is because we have to go beyond the superficial "buy guide" and into what works for you. The answers to this question can range from "my wedding outfit" to "a pair of pajamas at an all-nighter with my friends." Unfortunately, you can't exactly wear those to your job.

So let's look at those answers. Maybe you loved your wedding outfit because it was tailored to fit you. You took extra care of yourself that day, and it felt right to celebrate with an outfit that was literally set apart from the rest of your clothes. If this feels true, then maybe it's time to start treating the rest of your wardrobe with the same amount of thoughtful care. Get your stuff tailored, wear the nice jewelry, or the dramatic accessory. Hell, dry clean your jeans (my dad has done this my whole life, and his jeans have not only held up, they look great). Make getting dressed an act of thoughtful celebration, like it was for your wedding day.

You might be the one who answered "pajamas," because it was less about the formality of what you were wearing and more the joie de vivre you felt at the time. You were carefree, comfortable, and in good company. You were sharing fries and ideas into the morning, and it's that feeling you remember more than what you were wearing. Fantastic! Pajamas are both the height of comfort and the most intimate item you own. You wear your favorite worn-out t-shirts to bed, your comfiest pants or shorts that you wouldn't wear to the office (or even to the grocery)! If that's your speed, then find clothing that both excites you (colors, bands, a cool graphic) and makes you feel comfortable. I'd also suggest you take up a hobby like knitting or embroidery that you can do in a group. By the end of your project, you not only have something to wear, but it's imbued with the same kinds of memories.

2) What Are Your Current Values? What are the Things that Excite You Most? How Can You Incorporate That into How You Dress?

In certain fashion circles, this question elicits knee-jerk virtue signaling answers. Some people say "I value the environment," and by god, they mean it. Others say the same thing... right up until it's inconvenient. But it's an important question, because at some point in your fashion journey, you have to realize that none of this matters if it doesn't matter to you.

So I want you to answer this question truthfully and thoughtfully. No one's going to know the answer except for you.

But to make you feel better, and give you an example, I'll tell you my answers.

I value creativity. I love being able to customize my clothing or getting weird little trinkets from Etsy. I like to push boundaries with what I wear, and I'll probably try something that feels cool at the time but looks stupid in 5 years. That's okay, we can't get it right 100% of the time.

I value time with friends, so I wear comfortable things. We do a lot of outdoor activities, like hiking, climbing, and rock hopping. I'm not The Athletic Person, so I don't want to wear the latest in Gore-Tex. My bike shorts, big shirts, and old Doc Martens will do me just fine.

I value my community and my local environment, but I also value a good deal. I'm not the person who can afford to buy from B Corp Ethical Brands, and my size means I can't buy a lot of high-quality vintage gear. I'll buy local when I can, but I don't need another Mothman graphic-tee.

Because I can't always buy "the right things," I'll buy the right things for me and wear them into the ground. Then, if possible, I'll mend them and wear them into the ground again. I've cut up pants to become shorts, I've sewn up t-shirts too many times to count, and I've dyed old clothing to make it last another season.

Trends are temporary, bodies change, and life moves on. Even your values will change and evolve, and that's alright. But if you don't make a habit of asking yourself these big questions, everything, not just getting dressed, will be harder in the long run.

3) What Do You Need Right Now? Have you gone through a big life change? Has your body changed? Has your environment changed? How do these things need to impact your wardrobe?

This is one of those questions where the answer might immediately spring to mind (e.g., you're going back to the office after years of WFH). Write down whatever you thought of, but then I'd encourage you to keep this question in mind over the next few days. Make a note of whatever comes up, and write it down with the first part of your list.

Chances are you'll start seeing a pattern that goes beyond "more slacks and skirts." It'll probably be stuff like "I need clothing that is easy to clean," "iron free," or "softer fabrics." These are the things you need in your life, not just another black tank top.

For the necessities that go beyond the normal style guide, I always search for my answers on Reddit. They're more than willing to share their favorite stores for hyper-specific needs. You'll probably learn about some new solutions as well.

4) How Do You Behave in Your Clothing Now? How Do You Want To Behave in Your Clothing?

Think back to when you were first attracted to a distinctive style. You were probably a child or teenager, trying to figure out who you were, and this aesthetic was the thing that was going to help you do that.

At that age, we're rarely attracted to an aesthetic that doesn't have a lifestyle attached to it. Think of punk, old money, and eclectic grandpa. That's because you don't want to just look like these people, you want to know how to behave when you're dressed like them.

But you're not that Amateur Fashioner anymore. You've grown, figured some things out. Putting on the costume of someone else won't work anymore; you have to figure out your behaviors and how that affects your style.

This answer will be a mix of all three previous answers. As much as we need to look inward, at some point, you have to live in the real world. So, with all three previous answers at your fingertips, how do you want to behave in your new refined style?

Final Thoughts

Finding your style is a journey, and I'm excited that I got to accompany you on part of it. If you're looking for more inspiration, check out the rest of the site. You can also revisit the Stages of Your Fashion Journey to get a better handle on things.

Stay curious and stay hydrated, and I'll see you next time!