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How to Feel Beautiful in Your Clothes

January 17, 2020

I think most of us gals struggle with self confidence at times. And while we may become a little more comfortable in our skin by the time we’re in our 50s, many of us still don’t necessarily feel beautiful in our clothes. Today let’s talk about several ways we can become more confident and poised as we step out into the world.

You may look at my photos on Dressed for My Day or Instagram or Facebook and assume that I am one confident cookie. You’d be wrong. I’ve struggled with self esteem issues off and on throughout my life, sometimes feeling a little more confident than at other times.

How to Feel Beautiful in Your Clothes
red cashmere sweater // red blazer – sold out in red (similar and similar) / black skinny jeans // leopard print booties // hobo satchel (more economical option) // similar necklace // similar earrings

When I started this style blog almost two years ago, I had just lost about 20 pounds. So I had experienced a confidence boost that got me over the hump of self doubt that had been holding me back from doing this earlier. But even though I’ve kept most of that weight off, I have had to work at warding off those niggling self doubts as I’ve built this business.

The comparison trap has definitely lured me in and toyed with my confidence throughout this journey. So I put a lot of energy and prayer into keeping my eyes focused straight ahead instead of on others who {appear to me to} have it all together.

How to Feel Beautiful in Your Clothes

Probably like you, I have days when I get all dressed up and look at myself in the mirror and feel much less impressed than I had thought I would. The signs of aging, a little extra weight gained during the holidays, a bad hair day or just a feeling of malaise can take the wind out of my sails before I’ve gotten out the door.

Red Blazer and Red Cashmere Turtleneck

But I’ve learned that it’s just as crucial to “wear” a little self confidence as it is to put on a beautifully curated outfit. Clothing and a little makeup can enhance my appearance, but neither is a replacement for genuine joy.

So I’ve had a few “little talks” with myself about feeling beautiful in my clothes. And I thought I’d share some of my tips with you. These are the strategies and thought processes that have helped me to feel more confident in front of the camera, but also able to walk into a room ready to engage with others with poise and joy. And that’s really the goal, right? To feel confident and beautiful so that you can engage gracefully and authentically with other people.

Red Blazer and Red Cashmere Turtleneck

Tips for Feeling Beautiful in Your Clothing:

  1. Make sure your clothing fits. We gals tend to keep clothing in our closets in several different sizes…just in case. While you can certainly have clothing that’s one size up or down in your wardrobe, make sure you only wear the pieces that fit you perfectly. If you need to, take your clothing to a tailor. It’s worth the cost!
  1. Wear the colors that flatter you most. You absolutely do not need to wear certain colors simply because they’re in vogue. I completely sat out the coral crush last spring because that color does nothing for me. Especially wear your best colors close to your face.
How to Feel Beautiful in Your Clothes
  1. Practice good posture. Truly, practice it. I’ve found that I don’t just automatically stand or sit up straight. I have to work at it. Good posture can take years off your appearance, but it also helps your clothing hang better on your body.
  1. Put together beautiful looks ahead of time. Most of us gals are busy women who tend to dress the same way over and over out of convenience. There’s absolutely nothing wrong with that. In fact, I’m a firm believer in having a uniform or two. But with a little thoughtful preparation, you can put together go-to styles that include a couple of wardrobe essentials, a star piece, flattering accessories and the right shoes. Take a selfie of these “pre-sets” so you’ll know exactly what to put on when you’re in a rush.
How to Feel Beautiful in Your Clothes
  1. Stick with what works for you. Again, you absolutely do not have to participate in every fashion fad. Nor do you have to wear every kind of clothing. For instance, I talk a lot about blazers here on Dressed for My Day. But if you don’t feel absolutely beautiful in a blazer, stick with your cardigans or utility jackets. Wear only what makes you feel beautiful!
How to Feel Beautiful in Your Clothes
  1. Make an appointment with a stylist. Did you know you can make an appointment for a personal consultation with a stylist at many of your favorite retailers? Talbots has client specialists, Nordstrom has personal stylists and Bloomingdale’s has personal shoppers, to name a few. You could also simply ask the advice of another woman you know who always looks pulled together and stylish.
  1. Simply aim for modern. Don’t try to look younger; aim to look contemporary. There’s a difference, you know. When you try to look younger than you really are, you end up feeling like a caricature at best, a fraud at worst. But when you simply keep your look modern and up to date, you’ll feel like your most beautiful you!
How to Feel Beautiful in Your Clothes
red cashmere sweater // red blazer – sold out in red (similar and similar) / black skinny jeans // leopard print booties // hobo satchel (more economical option) // similar necklace // similar earrings

By the way, this post is also the second in the 5 Ways to Wear a Red Suit mini-series. You absolutely can wear red with red! Remember, tonal dressing is quite in style right now. And that’s a trend you don’t have to spend a dime to try!

I hope you enjoyed today’s post. Remember, you are beautiful. I just want you to feel as beautiful in your clothes as you look to us. When you feel beautiful, you’ll engage more gracefully and authentically with those around you. You have so much to bring to the table!

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You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

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Blessed for My Day

You have the opportunity today to influence those around you. Truly, you are an influential woman. Whether you’re simply setting the tone in your own home or you’re adding to the mix at work or you’re speaking into the life of a young person, you’re definitely contributing something to other people today.

Let’s make sure that our influence is positive and godly. We don’t only do that with the words we speak, however. We improve our influence when we conduct ourselves with a godly self assurance, when we bring a little joy with us and when we move forward with courage and conviction. Let’s get out of our own way today so that we can contribute well to the world around us.

Do all things without grumbling or disputing, that you may be blameless and innocent, children of God without blemish in the midst of a crooked and twisted generation, among whom you shine as lights in the world, holding fast to the word of life, so that in the day of Christ I may be proud that I did not run in vain or labor in vain. ~ Philippians 2:14-16

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xoxo, Kay
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21 thoughts on “How to Feel Beautiful in Your Clothes

  1. Hi Kay I love your blog and find it helpful in knowing what and how to dress .
    I really look forward to your emails and learn something useful in every one.

  2. Such a great post! Another one that will get a “double pin!” One pin in my Blessings board and one on my Outfit Advice board. Have a great day Kay!

  3. Kay, you have the best posts. I have a whole Pinterest board of your fashion advise and I refer to it often. I’ve recently turned 70 and for the first time in my life, I’m struggling with my age. Your posts encourage me to look my best everyday, and SURPRISE!, when I look good, I feel good. Thanks for the encouragement.

  4. Kay,

    Absolutely the best advice. Beauty comes from inside! Being yourself should always mean being your best! A simple smile goes a long way to brining out our inner beauty. You look confident and fantastic in todays outfit. Thank you for educating and guiding me to be my very best not only on the inside but also to take pride in how I dress. My Mom always said, “if you look good on the inside you will look great no matter what you wear”? Wise words!

    Have a great weekend! Rhonda

  5. Great post today! Always great to be reminded about feeling good in our clothing! It really does make a big difference when we feel confident in our clothes it shows!! You are a blessing!

  6. You look beautiful in red! Your blessing for the day is such a good reminder for me to always watch my words.

  7. Red is such a stunning color! I always seem to choose cardigans over blazers. I do like both looks.
    Thanks for sharing such timely advice.

  8. Dear Kay,

    You are a breath of fresh air in so many ways!
    Just a week ago I happened upon your blog, quickly and excitedly subscribed, and have already learned so much! I’ve read not only this week’s posts, but also from your archives. Especially helpful to me are your tips on proper proportion and sizing. For years, I’ve tended to purchase clothing too large or loose for my smaller frame. Additionally, I love to buy separates in solid colors, thinking I will mix and match from my closet, only to discover proportions are off somehow, or items don’t look good together. You’ve opened my eyes to clearly discern the 1/2-2/3 proportion principle and use it to my advantage. From now on, I’ll focus more on line and shape, and look to add investment pieces that will earn their keep through many happy wears.
    Please keep your creative and inspiring ideas and your prayers and thoughts for the day coming!

    1. Hi Julie. Thanks for introducing yourself. And I’m so happy that you are enjoying the blog. It sounds like you have been digging! I love that. Be sure to let me know if you ever have a suggestion for a blog post idea. Thanks for sharing!

  9. This is a very thought-provoking post. I like your idea of creating outfits ahead of time. Often when I am going out, I do not end up wearing what I had planned. Sometimes I don’t like the look or sometimes it is how I look / feel in the outfit. Then of course I try on numerous outfits, run out of time, and then “settle” for an outfit because I am now late. It’s such a simple idea I’m not sure why I haven’t done it. I mean, I create outfits all the time when I am packing to travel somewhere, why I haven’t I thought to do the same when I am home? Thanks, Kay!

  10. Love this post! Just as you said, Putting energy into prayer and focus on Jesus is so huge when Ifeeling the attack of comparison and insecurity. “Putting on” the armor of God is key and a cute outfit is icing on the cake! Thanks for blessing my day!❤️

  11. Love the idea of creating outfit ahead of time! And of emphasizing feeling good on the inside as well as the outside! Appreciate your blog and Blessed for my day each day!

  12. Hi Kay! I continually pray to God to help me with my critical views of my body now and how I continue to wish I didn’t have the excess skin in my midsection. I do plan my outfits for days I will be leaving the house. As a matter of fact, today I have put together complete outfits, including my handbag, for the upcoming Mon. – Wed., while I had the time to try on, if need be. Now all I have to do is iron a few pieces and I am good to go. I am very self conscious of the few rolls in my midsection, so I make sure to wear tops that coverup what bothers me. Posture is so important, isn’t it! I don’t have a problem sitting up straight. However, I do find myself leaning forward some when I walk, which is something my mom always fussed at me about. Why I wanted to stick my bootie out more as a youngster, I’ll never know. Thank you for having such a positive influence on me, in so many ways!