How to Find Your Own Style as a Woman Over 50

(Last Updated On: July 17, 2023)

Defining your personal style as a woman over 50 may not be a question in your mind. For some of us, preferences and style statements became crystal clear as we moved through our 20’s, 30’s and 40’s. Others don’t see things quite so clearly, and the confidence of knowing who they are in a style sense still feels hazy and undefined. So, we’re going answer the question of how to find your own style!

We’ll be covering quite a bit of information as we discover how to define our own personal style. I have a free worksheet for you at the bottom of the post. It’s a wonderful reference tool!

I worked in the banking industry for about 25 years back in the day, and it was very common for women in middle management positions to wear a two-piece suit with a blouse, hose and pumps. Except me. Matching skirts and blazers were never appealing to me. Boring, actually, were my thoughts at the time.

My preferred attire was more along the lines of putting two or three separates together to create an outfit, with the occasional dress thrown into the mix. I didn’t realize it at the time, but I was demonstrating my personal style as a young woman in a conservative industry.

Now that I’m in my 60’s and the banking world is in the distant past, I still prefer to keep things on a casual note for just about any occasion. That’s who I am. It’s my personal sense of style and I understand how and why I make certain midlife fashion choices.

I like to keep my life simple and relatively uncluttered, literally. I know from past experience that I don’t need much to be happy, and all the ‘stuff’ we tend to accumulate over the years isn’t that important. That overall philosophy spills over into my personal style, too.

I believe that for many of us, our fashion style sense evolves over time as we gain life experience, learn more about who we are, what we feel comfortable in  and how we want to present ourselves to ‘the world’. We make these decisions without conscious thought, we just know it is what we want to wear.

For others, though, it is is not quite so clear or simple. The process of learning how to find your own style, consciously or not, hasn’t evolved. Or, self confidence is an overall issue, including style. As we age and our bodies as well as life activities change, our style sense can become even more muddled.

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How to Find Your Own Style

Finding your personal style and midlife fashion preferences is not difficult. I have three simple steps for you here. You won’t find any technical, clever or dramatic terms for them, nor will you find this on any other site (not that I know of anyway, it came straight from my head and my heart). But, I know that it will help you be more confident in how you choose your clothes as a woman over 50, because you’ll be wearing what you love and feel good in.

The FIRST STEP in how to find your own style is to document what appeals to you.

I found this simple step very helpful in the past with interior decorating clients who didn’t know or understand their decorating preferences, and there are definitely some similarities with our own personal sense of style.

To do this, create a board (or several) on Pinterest and start perusing womens’ fashion pins. When you find one that appeals to you, save it. Don’t be concerned with the ‘why’ yet, just save it to a board.

If you prefer more of a scrapbook type of method, use actual fashion and other women’s magazines and tear out photos of clothing and styles that appeal to you. It could be as simple as gathering these outfits and putting them in a folder.

Again, don’t be concerned with the ‘why’ yet, just add it to your folder, journal or scrapbook. You will see a pattern emerge. It might be:

• consistency with color – you’ll see reds, blues, grays, or blacks in many of the images, for example
• or pattern – stripes, polka dots, plaids…or not…maybe it’s solids
• or fabric – organic fabrics, linens, denim, wool, for example
• or the outfit itself – you might see similarities in the layering of the outfit, the accessories, the shoes, the jackets, etc.

But there will be a pattern, even if the pattern is that there is a great variety.

Once you have a good number of images, see if you can place them in order of what you like the most down to those that don’t evoke much of a response from you.

Then, verbalize (out loud, in your head or in writing) what it is that you like about your top choices. I prefer putting thoughts in writing, as I tend to forget those pearls of wisdom and insight if I don’t document them.

Again, you will most likely see a pattern emerge. You are defining your personal style and documenting your fashion sense!

SECOND, take everything out of your closet

Yes…really. This is a very important piece of the style sense puzzle and it will become clear to you only if you do this literally. So set aside some time if you have a very full closet!

When I went through this exercise I placed each piece on my bed until the closet was empty, then considered each one individually. If you have an extensive wardrobe consider doing this in two or even three sections.

Put back only the clothes/accessories that make you feel good and confident and pretty when you wear them. Usually you will make this decision quickly as you look at each article of clothing (or accessory or shoe) because you will have an emotional connection to it. It’s a yes or a no. If you have to ponder and agonize over the decision, it is a no.

NOTE: If the actual removal of each article of clothing is more than you can attempt, that’s okay. You can also leave the pieces in the closet and examine them one by one. Just make sure you remove any of the articles of clothing or accessories that don’t make the cut.

Ponder the rejects…why did they not make the cut? You need to understand the no’s in order for the yes’s to make sense. Your reason could be related to size or fit…color or pattern…perhaps the style is now too dated for you.

I sometimes make spur of the moment decisions when shopping. I’m not even looking for any clothes, but spot something as I’m walking past and it ends up in my hand. Guess what? Most of those quick, thoughtless decisions are not ultimately a true representation of my personal style.

This is an important step so make sure you take the time to understand why you rejected a piece. You don’t want to go out and buy the same thing again on your next shopping excursion. Giving careful consideration to what you are going to purchase makes all the difference, my friend.

As women over 50, there are some clothes that might not make the cut because our bodies, our figures, have changed. I know that has happened to me. A pair of casual slacks or a top that I would wear quite often is now off the list. Why? I don’t feel good, or confident, or pretty in it anymore because I’ve changed, physically. It’s not a negative, it’s just reality.

You will most likely find some correlation between the photos in your ‘scrapbook’ that you rated as favorites, and the clothes/accessories that made the cut and returned to their home in your closet.

Even if you don’t realize it, you DO have a personal style as a woman over 50! You are learning how to find your own style!

THIRD, as you see what is now the wardrobe that represents your personal style, your midlife fashion, notice the one element that stands out.

Some might call it your trademark or signature look. There is most likely something that is a bit more dramatic, or colorful, or puts the finishing touch on your style statement consistently. This is part of learning how to find your own style and it’s an important point.

Here are some examples:

• a bold color or dramatic color, like red, black, bright blue or purple
• a dramatic print such as an animal print, geometric shapes, bright Hawaiian prints
• a particular type of jewelry, such as an oversized watch, statement earrings, chunky necklaces
• shoes…it might be the sheer number of them or a particular style that is trendy and fun

If you’re staring into your closet and scratching your head thinking, “I have no drama, no trademark, nothing stands out. I must be really boring”, not to worry, my friend!

Sometimes our “one thing” when it comes to our personal style is that we are ultimately creating an understated look. That is who we are.

Or, our “one thing” is more of a type of clothing choice or how we wear our clothes, so it doesn’t stand out so much. I like to wear my blouses and tops tucked in. I’ll wear the extra long tops with leggings at home in the winter months, but my style is to tuck in the tops, at least as long as I can continue to do that and feel good, pretty and confident!

Yours might be that you wear a blazer with your outfits, all the time. Or your tops might be similarly styled. You might love to wear the comfy pants with drawstring ties and long flowing tops over them.

We all have something that is our personal style definition and makes us unique.

My Personal Style in Midlife: Understated, casual and relaxed, with denim, black, simple jewelry and sandals (or black boots in cold weather) as my go-to fashion choices

It’s time to create your personal style definition

Now that you’ve discovered what your Personal Style is, take that new knowledge and put it into one or two sentences, like I did for my own style, shown in the box quote above.

It always helps to put thoughts into words…tends to make them tangible and memorable.

Additional elements of learning how to find your own Style

Once you go through this simple process of how to find your own style, there are a couple of other things to consider.

First, your ruthless dissection of the current wardrobe might result in a closet that looks rather sparse! If you’ve recently changed your lifestyle dramatically due to retirement or climate relocation, there might not be much left that is suited to you at present.

Ideally, you have the time and budget to plan out what you want to purchase to add to your wardrobe and accessories, now that your Midlife style and fashion sense has been discovered.

This might also be the perfect opportunity to consider a capsule wardrobe, and keep things really pared down and manageable. If that seems like a direction you’re not ready to take, consider a miniature capsule wardrobe for the holidays. It really takes the stress out of deciding what to wear to those special gatherings!

If not, you might need to pull back just a few things that aren’t ideal, but still workable for you. I have pieces in my closet (you know, those spur of the moment decisions) that don’t truly represent my personal style and are not my faves, but they’ll do until I can replace them with the clothing that makes me feel good, confident & pretty 🙂

Second, our current body shape and lifestyle are always factored into the mix. You might L-O-V-E the look of bold animal prints, but if your figure doesn’t love them as much, find a really cool scarf, or leopard print sandals, for example. You can wear what you love and still feel great about yourself.

We discuss body shape/type, style essence, style expression and other fashion related topics in detail in my Personal Development course for women over 50, Inspire Your Life.

Even if you’re not a fashionista, it is helpful to understand why you make the choices that you do in clothing, and how they relate to your personality as well as your body type and shape.

When you can mesh together styles that you love, wear those styles and feel good, confident and pretty in them, you’ve found your personal style and fashion sense as a woman over 50!

Sign up for the Free Resource Library and get the worksheet to help learn how to find your own Personal Style

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