Even if you once were on top of the image you projected through your clothes every day, it's easy to get stuck in a rut and stop noticing changes in yourself, perceptions, and the condition of those old favorite clothes.
For a lot of us, though, we've never been on top of fashion at all. Maybe like me you grew up comfy without a lot of pressure to worry about your appearance. That's ideal when you're a kid, but tough when you're trying to make a good impression professionally. Certainly like everyone you're carrying around some baggage from your past. Maybe it's a color or kind of clothing you're convinced you shouldn't wear because of something someone said long ago. Perhaps an urge to hide some part of your anatomy that you've built up embarrassment about – I see the early bloomers nodding here, remembering being the tallest kid in the class or the girl who first needed a bra, and hunching their shoulders forward. Or maybe you've just been following along with the trends as they pass through the stores and your closets, never having devoted the time to find and celebrate your own personal style.
I'm not suggesting we all suddenly need to be studying fashion magazines and spending all our money on the latest clothes. I'm working from a simple thesis:
Each of us looks better in some things than others.
So why not wear more of those things and less of the others?
Step One: Figure out what you like.
Start paying attention to what draws your positive attention. It's fine to also keep track of what you don't like, but the goal here is to begin collecting images that please you, especially those relating to fabric, color, silhouettes, but really anything can act as inspiration. Yes, certainly you can paste into a scrapbook, but I'd be wary of too much of that lest you focus on what's in current magazines only. You want to draw from a larger pool of ideas. Learn how to take screenshots on your computer (on Macs shift-control-command-4 is your friend!) and start grabbing those details for a journal kept in a word processing file. It's easy to copy an image to your clipboard and then paste it in with a comment of what you like about it.
Look through picture blogs like Nerd Boyfriend and Fashionist to attune yourself to people who are really shining out as individuals beyond as well as through their clothes and accessories. Take a look at this entry from Nerd Boyfriend about Michael Caine for a good example of how perfectly normal clothes can amplify a personality.
Be sure your explorations include things you're passionate about and explorations in unfamiliar environments. Expose yourself to new experiences and old things viewed anew.
Step Two: Figure out what you're like
You can do this in parallel with step one. What are your best qualities, both physical and otherwise? A great guide to this is the book 10 Steps to Fashion Freedom: Discover Your Personal Style from the Inside Out by Levene & Mayfield. Your local library probably has a copy. Give yourself credit for your great smile, beautiful skin, expressive hands, or whatever your best physical assets are. Accept and embrace your other strengths – are you reliable, funny, kind, resilient, patient, forthright, charming, sensitive, vibrant?
Decide what 2 or 3 things are the impression you most want to create. A few example personal style statements (taken from 10 Steps to Fashion Freedom) are "I project a substantial and meaningful presence", "I present a confident and sophisticated image", and "My personal style exudes quality and individuality." Your personal style statement needn't be completely reflected in your current best qualities, but should be supported by them. Make sure it works for who you are as well as who you're heading into being
Step Three: Take Inventory
What clothes do you have and how do they interact with your body? This can be a big project so you may want to take it in stages. Pick a category of clothes which are important to you either through frequent use or because you'll need them for an upcoming event. Don't pick the category which makes up the majority of your clothes; you want to get a quick sense of this step without exhausting yourself. Ideally do this with a camera with a self-timer in front of a full-length mirror with lots of good lighting. Bring in extra lights, especially if you have a lot of dark clothing or your pictures won't capture the details which will be useful later.
Do this when you have time to relax and are in a good mood. Do not let yourself bog down in emotional baggage or bad internal talk as you look at yourself. Remind yourself of your best qualities and stay on track. Personally I find staring in the mirror can be tough – I weigh more than I want to – so taking photos was a great way to get enough distance to assess what works and what doesn't in my wardrobe.
The big advantage of the self-timer is that you can get pictures of yourself from the back and the sides. I found a few surprises among my clothes where things which are very flattering in front have details which makes the bad fit strangely.
Work your way through this category – suits or formal dress can be a good place to start – and then take a look at your photos. What new things do you learn about your best features? I found my hands appeared far more graceful than I'd expected. What negative patterns in your existing wardrobe do you uncover which you'll want to avoid in future? When I looked at my outfits as others see them, I realized how many things I have which are way too big for me and are unflattering as a result.
As you look through your pictures, watch for colors which make you look great. It's amazing the difference a color which complements your skin and hair can make.
I wouldn't have guessed a charcoal grey would make the color of my lips, hair and, though you can't see them in this photo, my eyes more appealing, but it turns out to be a far more flattering color for me than pale pink.
Don't count on your photos as the best way to document your colors; like me, you'll probably find your lighting isn't good enough for that. A great resource in identifying them is to compare the good looking garments to Wikipedia's "shades of" pages which include samples and color names. So handy! Just take a little detailed screenshot of the color you need and start to build up your palette in your style journal.
Step Four: Cut out the bad choices
Life is too short to wear stuff that makes you look crappy. Friends & family, charity, or trash, just get the worst stuff out. Better to have fewer choices than constantly have to route around the bad ones, especially when you're tired or feeling low.
I found it helpful to think about the clothes I'm keeping as belonging to two main categories: best and casual/adequate. The latter includes not only very informal clothes, but also ones which show too much wear to remain in the "best" group. There are also some in this group which are in good condition, but in a less flattering cut or color than I'd ideally like. Note that anything out-and-out unflattering hit the donation bags, these are just the ones that are "okay for now".
In future, I want to buy primarily into the "best" group with the idea that most if not all of my informal clothes should be of such good quality that they could migrate over to loosen up an otherwise dressy ensemble. Think about the impact, for example, of a really good pair of jeans worn with fancy shoes and a stylish blazer and shirt. That same pair of jeans could be worn with hip sneakers, a plain silk blend t-shirt, and a cool hoodie from an indie designer to create a fully casual outfit. Or any of the other parts of that casual outfit could be pulled in with more formal pieces to add ease and character.
If it's all good stuff and it looks great on you, mornings get a lot easier.
Step Five: Take opportunities to upgrade
As you eliminate garments or relegate them to your "merely adequate" group, start a wishlist of replacement pieces which will be more flattering in fit, color, and in reflecting your personal style statement. As I write this there are three pieces in my physical inbox awaiting addition to my shopping wishlist with notes "get this style in one of my colors", "too large! replace with a medium petite, ideally in a more coral pink & less salmon color", and "too long in body & sleeves, too loose in waist; need petite?".
Unless you're blessed with a huge budget or were fortunate enough to have a great collection of clothes already, pick out one to three pieces on your wishlist which you most need and which will be most versatile and just get those for now.
Don't forget to be creative with how you turn bad clothes into good; consider trading your clothes at a second-hand store you like that has regular buying days and use that credit to shop their shelves for your wishlist items.
As with most of life, just start leaning each of your choices in the direction of the future you want to have and you'll be amazed at the progress you'll make in six months or a year.