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10 Questions to Help You Make the Best Style Choices

Building a Wardrobe
January 26, 2021

I believe that one of the best kept secrets of the most stylish women is that they know when to say yes…and when to say no…to style choices. The most stylish women – the ones who always look effortlessly pulled together and tastefully chic – know that they don’t have to participate in every fashion trend, utilize every style hack or wear every trending color to stay in step with style. Today let’s take a cue from these women and learn ten questions we can ask ourselves so we can make wise style choices and look as fabulous as they do…without copying every single thing they do!

10 Questions to Help You Make the Best Style Choices

Actually it might be a good idea to keep these questions handy as we begin talking about 2021 fashion trends and colors soon. And as we replenish our spring and summer wardrobes, we’ll be wise to review these questions again. In fact, I’d suggest asking yourself these 10 questions each time you read my blog posts, especially when, like yesterday, I’m offering style tips. Not every tip I offer will work for you.

That’s right. You heard it from me. A stylish woman will have to weed through the advice I give here and find what works best for her. Let’s get going on those questions, and I think you’ll see what I mean.

Each time you consider adding a trending color or style, trying out a current style hack or wearing a new piece of clothing, first ask yourself…

Q #1 – Does it fit my personal style aesthetic?

My personal style aesthetic or style essence is classic with a modern, sophisticated twist. Those are my words. I made them up. You get to make up your own personal style essence, too. Every woman gets to determine for herself what message she wants to communicate with her clothing choices.

Consider Your Pants Choice When Wearing Socks
Shop the Look.

And that’s exactly what a style essence is, by the way. It’s what you communicate to the world with the way you dress. If you still need some help determining your personal style essence, you might enjoy taking my little style essence quiz. If you’ve already done that and still don’t know your personal style aesthetic, read or review How to Define Your Signature Style.

Stylish women have put their signature on their style and wear it boldly.

Q #2 – Do I like this?

Shoot. If you don’t like a particular garment or color or style hack, stop right there. Again, you absolutely do not have to participate in any trend or formula you don’t absolutely enjoy. My 27-year-old daughter does not like any clothing that features buttons as decoration. I don’t know why. It doesn’t matter. If she doesn’t like a sweater like mine below which feature buttons on the shoulder, she shouldn’t buy it or wear it.

Buttons on the shoulders
cableknit sweater // tassel necklace // earrings // similar shirt

Of course, I also believe a truly confident and beautiful woman will not need to tell everyone she doesn’t like something. Especially if other people seem to be enjoying that garment, color or style. Ahem. No, the most stylish women just quietly choose the things they like and allow others to enjoy those they don’t without feeling or intimating that they are somehow right and others are wrong.

A stylish woman enjoys wearing what she likes.

Q #3 – Does this work well in the wardrobe I’ve cultivated?

In 2019 I did a pretty extensive blog series about Building a Wardrobe that Works for You. If you haven’t read that series of posts, you can always find them in the top menu under FASHION. But I suggest you start with the post, 9 Keys to Building a Wardrobe that Works for You.

Building a Wardrobe that Works for You

The bottom line is that rather than just accumulating clothing you like, you might want to build a wardrobe that works together beautifully. Anytime we consider bringing a new garment or accessory into that well-cultivated wardrobe that we’ve worked so hard to fine tune, it’s wise to ask if it will “play well” with other things that are already in your closet. If it doesn’t, resist the urge!

A stylish woman curates a wardrobe that works for her over time.

Q #4 – Is this a color that is in my selected personal color palette?

Now if you’re considering adding a garment or accessory in a new and trending color, it may well not be in your chosen color palette. That’s okay. But if it’s not, you’ll want to consider purchasing that new color in an accessory or inexpensive garment such as a t-shirt rather than a wardrobe essential or expensive garment.

Ankle Jeans More Front Tuck Ankle Boots Showing Blousy Sweater
sweater // jeans // boots

But it’s so important for us to embrace the colors we’ve “limited ourselves to” because this limit is actually going to serve us well in the end. Remember, the stylish woman knows when to say no. Saying no to a trending color doesn’t mean you can’t enjoy it; it just means you’ve wisely determined a) it’s not a great color for you or b) it doesn’t play well in your cultivated wardrobe.

Want to know more about choosing the colors of your wardrobe? Read or review How to Choose the Colors of Your Wardrobe.

How to choose the colors of your wardrobe - Building a Wardrobe that Works for You

A stylish woman wears the colors that make her look and feel her best…regardless of what’s “in.

Q #5 – Does this work for my body shape?

As thrilled as I was that so many readers enjoyed yesterday’s post on wearing socks stylishly for winter, I was also actually quite glad to see a few women commenting that some of my tips might not work for them. That shows me you’re thinking through many of these questions. And one of the most important questions to ask yourself when I suggest a style hack or formula is “Does this work for my body shape?”

For instance, if you’re an oval shape, you may just need to tune me out when I suggest tucking your shirt. That doesn’t hurt my feelings one iota. I don’t want to give you bad advice. But only you can determine if something I or any other blogger suggests is good for your body shape.

Learn more about how to identify your body shape and/or how to style your body shape in my Dressed for My Day My Way style series, always found in the top menu under FASHION.

Discover Your Body Shape - 5 Female Body Shapes

A stylish woman knows, embraces and dresses her unique body shape.

Q #6 – Does this help me create the most pleasing proportions?

But it’s not enough to know our body shape. We also need to know and constantly consider our unique body proportions. The goal is to use our clothing and accessories to create a “golden ratio” in which one portion of our body appears to be roughly 1/3 longer than the other. The longer portion could be the top, as when you wear a dress, or the bottom, as when you wear long pants and a shorter top.

However, your unique body proportions have to factor into creating those pleasing proportions. If you are high waisted with long legs, then you may not need to tuck in your shirt to create those magical proportions. But someone with a long waist and short legs will almost have to wear higher waisted pants and cropped tops or tuck that top in to get those same proportions. Make sense?

How to Discover Your Body Proportions Measurements
Learn more about how to determine your unique proportions.

You can learn more about how to determine your unique proportions and how to dress your proportions in my Dressed for My Day My Way style series, always found in the top menu under FASHION.

A stylish woman knows her unique body proportions and how to work with them optimally.

Q #7 – Will this draw the focus where I want it or where I want to avoid it?

Again, one of my readers pointed out that the style tips I proposed for wearing socks in yesterday’s post would draw the focus to her shoes. She was absolutely right. For many of us, that’s not a problem. But for her, it would be. This is a woman who knows what parts of her body she wants the focus to be on and those where she’d rather divert the attention. Smart lady.

Do you know what part of your body you want to draw attention to? Don’t say none. That’s not a good answer. I like to draw focus to my eyes and my balanced proportions. I also don’t mind having focus on other parts of my body. But I work pretty hard to divert attention from my calves and my upper arms.

Winter Classic Outfit with Black & Grey
Shop the Look.

A stylish woman knows her assets and draws attention to them appropriately and tastefully.

Q #8 – What does this garment (trend, color, style hack, etc.) communicate?

The science of enclothed cognition purports that our clothing says something about us to other people. Not only does it communicate our style choices, however. It can also carry deeper meanings that we may or may not be aware of. We’re wise to consider the messages our clothing communicates about us.

5 Ways to Wear a Red Suit
See the original post.

For instance, if you are in a position where you need to exude authority and intelligence, you may want to wear more red and/or black. If you need to earn the trust of your clients, patients or students, you may choose to wear more blue. And if you want to put your teammates at rest and ease, then you may select to wear green. And those are just colors.

Your footwear choices, sleeve length, collar and fabric choices also communicate subtle messages to those who encounter you. Consider what your clothing and the way you wear it may be saying to other people.

A stylish woman knows her influence and uses her style to accentuate it.

Q #9 – Does this work on my frame?

Besides considering your body shape and proportions, a stylish woman also takes into account her frame. If you’re petite, for instance, you may not want to carry a large tote bag that would only overwhelm you. But if you’re tall or large framed, you might want to think again before choosing to wear that trendy skinny belt.

Bold & Sassy

A stylish woman embraces her unique frame and uses it to take up the space she is due.

Q #10 – How do I feel in this?

When all is said and done the most beautiful thing you can wear, besides your smile, is a little self-confidence. And let’s face it, you’re more likely to smile if your confidence level is high.

Sometimes I love the idea of something. But when I put it on my body, it just doesn’t work. Maybe it doesn’t feel like me; it doesn’t feel authentic. Or maybe it feels itchy. Or maybe it binds and bulges or sags and bags. Whatever the case, it doesn’t feel good.

On the other hand, when I feel good in my clothes, it shows.

Stylish women feel good in their clothes and it shows.

Now, that’s not to say we should never push ourselves beyond our comfort zone a little. I do believe that some new trends or style hacks take a little (or a lot!) of getting used to. So don’t be afraid to give something new more than a few spins around the block before determining if it’s a good fit or not. Otherwise we could easily talk ourselves into just wearing our pjs all day, every day.

Also, I’m not talking about fit here. Obviously fit is key. But that’s a question to ask of a particular garment. The ten questions I’ve posed here are more for trying out a new concept. But, yes. Definitely make sure your clothes fit.

Thank you for stopping in today. I appreciate you reading today’s post. Let me know if you have questions or thoughts you’d like to share. Have a great day!

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Blessed for My Day

Today I pray for you to feel God’s presence as you walk through your day. May you know and experience His constancy in your life. And may you hear His voice above all the other voices that clamor for your attention.

While we may think that kind of intimacy comes only through solitude and meditation in God’s presence, the Bible teaches us that as we walk blamelessly in the world we actually grow closer to God. Until God takes us out of this world, we have a responsibility to live in it in a way that reflects His grace and holiness and love to the people with whom we come in contact.

O Lord, who shall sojourn in your tent?
    Who shall dwell on your holy hill?

He who walks blamelessly and does what is right
    and speaks truth in his heart;
who does not slander with his tongue
    and does no evil to his neighbor,
    nor takes up a reproach against his friend;
in whose eyes a vile person is despised,
    but who honors those who fear the Lord;
who swears to his own hurt and does not change;
who does not put out his money at interest
    and does not take a bribe against the innocent.
He who does these things shall never be moved. ~ Psalm 15:1-5

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xoxo, Kay
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25 thoughts on “10 Questions to Help You Make the Best Style Choices

  1. I love everything you do!! Keep up the great work❤️
    I have a wedding in June, I’m sixty eight, 5”4’, 150 lbs and I don’t wear heels. Looking for dress up ideas.
    Thank you so much for your work. It makes my day.

  2. OH! I love what you wrote! I have 2 daughters in their twenties — THIS is going on my refrigerator!
    “Of course, I also believe a truly confident and beautiful woman will not need to tell everyone she doesn’t like something. Especially if other people seem to be enjoying that garment, color or style. Ahem. No, the most stylish women just quietly choose the things they like and allow others to enjoy those they don’t without feeling or intimating that they are somehow right and others are wrong.”

    And those 10 questions are so helpful. I am passing this along to friends. You explained it so well. Thank you Kay!

  3. Excellent advice! Since I started following you, early on in your blogging career, I have learned so much. I now look for relaxed classic with a colourful twist styles! I have my neutral base colours and my select signature colours. I know my body shape and proportions. So when I hit the change room or am trying on clothes at home I follow my rule…Do I love it and does it love me back? If I don’t answer a resounding yes to both back it goes!

  4. I am now retired after wearing scrubs for 40+ year career. To be perfectly honest my closet didn’t meet my needs. I didn’t know where to begin! These questions and your blog have challenged me to step back, assess and make some purposeful choices. Thank you so much!!!!!

  5. What an absolutely fabulous post, Kay! Thank you so much for sharing such great information with us. This is one of the posts I will need to keep referring back too.

  6. This type of posts is what puts you way above some other fashion blogs. I love them all but some are just pic after pic of the blogger wearing outfits. I love all the valuable information you pass on to us.

  7. Another well thought out and well-crafted post, Kay. I think we often consider these ?’s intuitively, but it’s so helpful to wrap words and numbers around them. Anything to help us remember!

  8. I’m new to your blog and I really enjoy it. Your advice is excellent and I especially appreciate when you also suggest what NOT to wear in your commentary. That is very helpful.
    I’d love to see you do a post about shoes, specifically what type of shoes go with different pant styles—skinny, wide leg, ankle, crop, etc. Thank you!

  9. So many great posts lately Kay! (okay — they are always good, but holy cow girl. . . you’re on a roll!) You’ve got us gals thinking, curating, planning and shopping. Thanks for all you do to be a cheerleader for the over-50 woman.

  10. For me…..I really just need to “try” the outfit on first to see how it looks and makes me feel, if that makes sense. I do really like an all over one color on me but makes me look way too thin so I need to add a pattern. I also like to shop for less expensive “trends” at Walmart, TJ Max, etc. because when it goes out of style I don’t feel like I’ve wasted my money. I love all these points you have asked us❤️

  11. I just saw your latest video about how to look “modern”.
    I overall enjoyed it but there is a bit of a discrepancy in your message. When you were talking about
    makeup you said you no longer wear eyeliner or shimmer makeup and think it ages you. You referenced Angie of Hot and Flashy as well as Dominque Sachse. I have been following them for years. Both wear eyeliner as well as shimmer makeup… on the eyes and always use highlighter. Maybe you are not comfortable with it but both of those look modern and not outdated.

    1. Actually Domique’s recent video suggested only putting eyeliner right into the lash line and being very careful not to create a heavy line over the lashes. My coloring is different from hers and I have a hard time seeing to apply liner the way she describes so I’ve opted out. I don’t think I said that everyone should do the same. I just said that’s what I’ve done because I don’t want a heavy line that can weigh our eyes down. And while both of them may wear some shimmer, I prefer not to. I didn’t say they said not to. I’m quite aware that they both wear some. I just don’t. Sorry if there was confusion there. I didn’t mean to imply that I got that advice from them. I just mentioned them after I talked about my own personal choices because I know women are always looking for good makeup advice and they both offer it.

  12. Could you tell me how you ask your hair stylist to cut your hair. my hair is about your length (gray) and I am thinking of adding some type bangs. I like that yours are not heavy. Also, is your hair layered on the ends. Your hair is very pretty and casual looking. I do not like structured over hair sprayed. Thanks

    1. Hi Linda. It’s called an updated shag. Your stylist should know what that is. It is layered and she also too a razor to it for texture.

  13. I really loved the questions to ask about clothes! I love your style of dressing but my style is more of the sporty style. I do a lot of walking and exercise type activities. Right now I am in VT going XC skiing and snowshoeing. Your advice is wonderful and I am going to use some of it this summer when I have to get some new clothes. I have a hard time with fit because I am 4’10” tall. Hope you have a great day!

  14. Hello Kay, I have just started receiving your blog emails. I <3 the information, and the way that you deliver it, recognizing that each woman should embrace and love their own bodies. But, my absolute favorite part of your daily blogs are the verses at the end. I spent many years on the worship team at church, and on women's ministry, and even spent a year cleaning the bathrooms as service to the church. For many reasons I fell out of attending church, and really didn't realize how much I missed the socialization with Christian women, until now. Thank you for reminding me that Christ is with me.
    Blessings to you!!

    1. Welcome, Gail. I’m so glad you are a new subscriber. I hope you continue to enjoy the blog. Thank you for your encouraging words. I needed that today. ?

  15. Kay,
    Your hair was so stylish in this posts. Looks good in any style but so smart and flattering in this shoulder length style!