Are you on the constant quest for good style, but it eludes you? Or maybe you have used a style quiz to figure out your personal style, but you’re struggling to create outfits on the daily that resonate. Perhaps you still catch yourself making purchases you later regret because they don’t actually work for you. My bet is you may be struggling with what I call “style discernment.” It’s hard enough to be discerning in other areas of life, but fashion presents its own set of challenges when it comes to making wise purchasing and styling decisions. So today I’m sharing the skill set that unlocks great style confidence for women over 50, so that you can make wiser choices as you build your midlife wardrobe and put together outfits you truly enjoy in this season of life.
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Unless we are naturally gifted stylists – and few of us are – we all struggle at times with defining how we want to look and with curating outfits that emanate that style. And especially as we transition from one season of life to another, we are prone to question our sensibilities and choices. So there’s no need for you to feel like it’s just you. You’re not the only woman who makes regrettable purchases occasionally, stands in front of a closet full of clothes and panics or ends up with a pile of clothes on her bed before finally walking out in an outfit. We’ve all been there. I certainly have.
Foundational Principles for Developing Style Discernment Over 50
Style discernment is the ability to make sound, independent judgments about what aligns with your personal values, preferences and goals, rather than blindly following trends or external pressure. Developing these skills involves a blend of self-awareness, critical thinking and practical application.
Know Yourself: The most crucial first step is to understand your own values, interests, and what brings you joy. This self-knowledge acts as your internal style compass, helping you filter out what doesn’t align with who you are or who you are becoming. If you’re struggling to discern your personal style, check out my blog series, Define Your Style…Refine Your Wardrobe (start with the bottom post).
As a woman over 50 you’ve undoubtedly experienced a few changes in your personal life in recent years. Perhaps your lifestyle looks different, especially if you have changed professions or retired from work. You may no longer be raising a family, and now you have more free time. Or you may be taking care of a loved one, so your days include more time in service and at home. Consider how these personal lifestyle changes impact your style preferences. And there’s no wrong answer here. To your own fashion values, interests and lifestyle requirements be true.
Embrace Critical Thinking: Discernment requires analyzing information objectively and evaluating its credibility. Don’t take everything at face value; question assumptions, identify biases (both your own and others’) and look beyond surface-level details. That means you’ll want to sift through what I and other bloggers/influencers tell you when it comes to style advice. Take in our content through the sieve of your own preferences, body type and features, budget, body proportions and lifestyle.
Cultivate Mindfulness and Reflection: Developing discernment requires that you slow down your decision-making process. When it comes to editing your wardrobe or purchasing new selections, create space for reflection to pause, disconnect from distractions and be present with your thoughts and feelings without judgment. This practice helps you gain clarity and avoid impulsive decisions.
PRO TIP: Shopping sales can be a huge stumbling block to practicing style discernment. If you know you are prone to hasty decisions and impulse buys, make sure that you go into sales with a clarified wish list developed over time and thoughtfully.
Trust Your Inner Style Compass: While guides and logic have their place, the most valuable tool in your style arsenal is your intuition—that “gut feeling.” Pay attention to your bodily responses when you try something on: does that silk blouse give you a subtle lift of confidence or does it make you feel self-conscious? Does a new color palette bring a feeling of ease and clarity or a tightening sensation of discomfort?
At this stage in life, you have decades of lived experience to draw from. Learn to distinguish between passing trends and an authentic inner voice that whispers, “This is me.” Honoring these feelings helps you filter out external noise and commit to a style that truly resonates with who you are now, not who fashion dictates you should be.
Practical Steps for Skill Development
Seek Diverse Style Perspectives: Actively engage with a variety of style inspirations to broaden your knowledge and challenge existing assumptions about what is current, stylish or “age-appropriate.”
- Instead of defaulting to the same catalog you’ve always ordered from, explore fashion blogs and Instagram accounts featuring diverse women over 50 (and younger women, too) who possess styles you admire.
- Solicit feedback from a trusted, honest friend whose style you respect (“Does this color wash me out, or give me a glow?”) to gain valuable, objective insights.
- When shopping, listen to sales associates, but ultimately process their suggestions through your own internal filter, paying attention to how you feel in the garment rather than just what you’re told is “flattering.”
Practice Asking Quality Wardrobe Questions: Develop a habit of asking insightful questions before making a purchase or choosing an outfit for the day. These questions help uncover blind spots and clarify if an item is a true asset to your wardrobe.
- When considering a purchase, ask yourself: “Does this piece align with my current lifestyle and values?” “Will I feel authentically ‘me’ wearing this?” “Is this an impulse buy based on a sale, or a thoughtful investment?”
- Before getting dressed, ask “Does this outfit feel comfortable and elevated?” “Am I wearing this dated item out of habit or genuine preference?”
Learn from Experience and Feedback: Reflect on your past style decisions and their outcomes, using both successes and mistakes as data points.
- Take a moment to notice when you receive compliments that feel genuine, not just polite—these are clues that you’ve hit upon a look that suits you.
- If you wear an outfit and tug at it all day or feel uncomfortable, make a mental note (or snap a quick, private photo) as a reminder that the fit or fabric was a “mistake” to avoid repeating, not a failure.
Manage Emotional Reactivity to Trends: Be aware of your emotions and how they might influence your judgment. Practice self-regulation to counter anxiety or the feeling of being “left behind” by the latest trend.
- If you feel pressure to wear wide-leg jeans because “skinny jeans are out,” pause and examine the emotion driving that thought. Are you worried about looking dated, or do you actually like the new silhouette?
- Approach fashion with curiosity rather than a frantic need to keep up. When you see a new trend, observe it without immediately assuming you must adopt it; this allows for a more objective assessment of whether it works for you.
- On the flip side, if you tend to have immediate negative reactions to all trends, consider if you’re clinging to past fashion silhouettes and features out of a sense of comfort, loss, familiarity or resistance to change.
- Cultivate a sense of looking for “modern options” rather than “chasing the trends.” The difference is subtle, but worth contemplating.
Curate Your Fashion Influences and Environment: Be discerning about the information and external influences you allow into your awareness.
- Declutter your social media feeds by unfollowing fashion accounts that make you feel inadequate or confused, keeping only those that genuinely inspire your personal style journey.
- Limit mindless browsing of fast-fashion sites that push endless consumption. Freeing up that mental space helps you hear your own preferences more clearly.
- Curate your physical closet, removing items that don’t fit your current life or body, creating a wardrobe that is an intentional reflection of your present self.
I like to encourage women over 50 to “get dressed for your day” because I believe you should still boldly take up a little space and show up looking like your best self. You’ve earned the wisdom to know what suits you best. Trust that inner voice. But also decide for yourself who and what to listen to as your personal style continues to evolve. Take these steps one outfit at a time and embrace the courage to dress for the amazing woman you are today. Your most stylish chapter starts now.
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Blessed for My Day
Most of us are quick to criticize our leaders when they make what we deem to be foolish decisions. And it’s true that when a leader lacks discernment they are prone to create an environment in which chaos reigns. No one wants to live in that kind of situation, so we naturally worry when we detect a lack of wisdom.
But let’s consider our own closets – for sake of example – as our own little country in which we are the rulers. In the same way, if we make hasty decisions swayed by popular opinion or insistent voices, we also run the risk of creating chaos and disorder. And if govern our closets with a plan, a sense of well-grounded confidence and decisiveness, we risk mayhem and defeat. So it’s wise to govern our closets and, yes, our style choices with intelligence and discernment. And since our fashion sensibilities can affect our self-esteem, our relationships and our budgets, I even think it’s worth praying about if you feel overwhelmed in this area of life. What do you think?
When a country is rebellious, it has many rulers, but a ruler with discernment and knowledge maintains order. ~ Proverbs 28:2
Excellent Dressed for My Day and Blessed for My Day post today!
Your post is AMAZING! I’m a true pear shape and tunics when I can find them truly look the best on me. I feel free and can still wear the styles that make me feel the best! Thank you!
What a great post! It resonates with me in so many ways especially the slow down and really think about what you need and does it fit with the image you want to project. Sometimes I make a purchase and let it sit in the bag in my bedroom. Then I go back and try it on a few days later and think if I really want this or do I need it. All I can say is thank goodness we can return stuff!
You look awesome in the clothes you wore today. Because I believe my coloring is close to yours (intensity, etc), I will be looking for this sweater. I love the color.
When shopping, I have found that if I wait a week or two before buying or passing on an item, this helps me decide. There is a beautiful sweater that is colorful and youthful looking that took me two weeks to purchase. I knew that if it haunted me, it was right for me. Plus I could pair it with at least three other items at home. Although an investment, it worked out even more successfully than I imagined. This method has helped me often in the past.
Thank you for all the pointers you gave on curating my closet. These are perfect for me as I rebuild my wardrobe due to size and life changes. I will be rereading this blog in the future.
Enjoyed reading your tips on what to ask about your closet and your lifestyle. Good information to debate. Sometimes I feel I should think about an item before I purchase it instead of buying everything I like right away. I have made some bad decisions because of this. Sometimes I buy right away to get the sale or before they sell out of the item. Lots of times I end up returning the item. I wish my favorite boutique was still in business in my town. Covid put her out of business and don’t have any main stores or shopping centers close around. Over 45 minutes away. I miss going into the stores and trying on items.
This was truly a knowledge packed Dress for My Day
So much info and easily relatable
Your outfit today too was amazing the color just perfect on you also
Thank you
Great post. I’m learning at my age to really think before a purchase and you are soooo right…..sales can mess a person up. LOL This time of year I find myself seeing the great buys by the stores I love and I really don’t NEED something, but its just too good a deal to pass up. I’m trying harder to buy for my life style, but still struggle then when i need something more dressy and don’t have it.(my lifestyle is very casual, yet modern and put together). Even with my casual dress, I find I look more dressed up than others in my area. i think people still dress down since covid, don’t you? Thanks for your wisdom and discernment to help us dress our best.
Thanks so much for this, Kay. There’s so much helpful info. I’ve made a couple of iffy choices recently, so it’s timely for me!
I agree with others, Today’s outfit is exceptional–distinct and so flattering.
What an interesting post. Much to think about and appreciate you sharing your wisdom on the topic. I struggle myself with putting outfits together. I have starting taking pics and trying to change up an outfit if something looks off. A work in progress for sure but I have learned a ton from you Kay, So thank you!
Wow – all so true, and also true that it is really hard to shop well; much harder than one would think! Sometimes I almost feel guilty for the amount of time I put into thinking and reading about clothing, shopping, etc., but then I consider it a kind of hobby, I guess, or a distraction from problems in my life that seem intractable. The desire to look as good as I can, the desire not to be overly influenced and wind up feeling foolish with things I won’t wear, coming to grips with the facts of an aging body and face that at times are so disappointing, balancing budget considerations, trying not to purchase things that don’t fit how I really live or require care I won’t want to give – there is a lot that goes into buying clothes! I really appreciate today’s “deep” post.
Thank you for the good fashion advice. This season I’m doing better not buying things I don’t need.
Thank you Kay for pushing us back into a realistic way of purchasing and good decisions about our way of purchasing and dressing. Yes I am guilty of too many items in my closet, and sometimes I have the urge to get rid of all and just have a few choices. I take your words to heart and promise myself to do better. Thanks for the push to do better.
I do think it’s worth praying re. our fashion sensibilities. Recently, I just feel overwhelmed at all the sales pitches from stores, bloggers and everywhere. I enjoy looking at clothes especially, but I have a closet full of nice things. Also, my Xmas shopping is done and there really is nothing I need or want. Many of your outfits are things I’d wear, so it’s nice to get ideas. Thanks.