I use multiple approaches to style needs when working with clients. Understanding these different approaches is likely to be helpful in your personal style journeys.
The first asks, "Who do I want and need to present to the world? What is required of me? What do I want to invoke in others when they see me?" How you want to be seen is an interconnected and social approach. It may also be beneficial in your professional life to cultivate an image through considering your intended effect.
The second asks "What do I feel comfortable in? What makes me feel safe? What makes me feel joyous? What makes me feel free?" How you want to feel is a personal approach. It may be how you feel when you see or touch the clothing, or how it feels against your skin, or how it feels to move in it.
The third asks "What colors, shapes/silhouettes, and textures are most flattering on me?" Wanting to know what's most flattering to your form is an analytical approach. This approach is like a puzzle- trying to figure out the different aspects of your form and movement/personality and echo these aspects in your clothing choices.
The fourth asks, "What do I realistically need for my activities in life?" Understanding activity needs is a practical approach. What percent of your time do you spend doing what activity? Do the contents of your closet match up with these percentages?
Much of the struggle that I see with people trying to sort out their own style comes from trying to wrangle these separate approaches simultaneously. They say things like, "I know I look best in soft fabrics, but I really love sharper looks" (analytical approach conflicting with personal) or "I have to present a serious image, but I just live for cartoon prints and fun, silly things" (social approach conflicting with personal) or "My friend buys me heels and wants to see me wear them, but they don't fit into any aspect of my lifestyle" (practical conflicting with social) and they feel dissatisfied and frustrated when trying to come up with a wardrobe that attempts to value two or more approaches equally and simultaneously..
I strongly recommend that you consider these approaches separately.
Write separate paragraphs and/or lists to focus on
- how you want to be seen
- what makes you feel happy to wear
- what is especially flattering in terms of color/lines/etc
- what your activities currently require of you.
No cross-referencing during this initial phase- just try to answer each of the approaches for themselves without worry of trying to find points of intersection- there might not be any, and that's ok. You may need to break your lists into sublists if you have different answers depending on the arena of your life (e.g. How you want to be seen by your boss, your friends your partner, your baseball team, etc).
Order your four lists in order of importance. If your boss requires a specific dress code and it isn't at all what you would personally choose to wear, you might not be able to place what you feel good in above the importance of your life activities or social expectations in that arena, at this time in your life. Don't fret, as there are ways to integrate happy-feel-good items into even the stuffiest uniform.
It is really important to be clear on what your current style priorities are for the different realms of your life. It is ok to keep them separate, and it is helpful to know in your mind that they are separate, as well as your reasons for keeping them separate, so that you aren't left frustrated in trying to make one cohesive look out of multiple, separate, needs.
For a long time my personal hang-up was in making fitness clothes as stylish and flattering as possible while also staying practical. Realizing that flattering, personally joyous, practical fitness wear couldn't be equally those things has allowed me to stop the endless search and to appreciate what I do have for being practical and at most ticking one other box.
One of the most common modern style dilemmas is the personal feel-good desire for comfort and a separate desire for the most flattering lines. These are both good desires, and it is infinitely helpful if you know which desire is a bigger priority, if only by a sliver, so that you can make quick calls when shopping or getting dressed each day, and shed the frustrations and confusion that unclear priorities bring.
When you have your separate write-ups, you can begin to ask yourself questions about each- "What is it about these things that makes me feel happy? Is there something I can carry over to bring joy into other arenas of my style? How much wiggle room to I have in my life activity needs? What are the possibilities?"
It's helpful to remember that while an entirely cohesive wardrobe is satisfying, it's not always possible, and at the root, it's not necessarily what we want when we consider that we have different needs and desires in various realms of our lives.
Now when you declutter your closet, or when you shop, you can ask what approach or arena of life you're looking for, and how it fits into your current priorities.
If you feel like sharing some of your answers to these questions in the comments, I'd love to hear them! If you think of other approaches, please share those too.