How to Dress With Confidence, No Matter What Your Day Holds

This post is sponsored by The Mint Julep Boutique. I only highlight and share products that I use and truly love. Thank you for supporting the brands that support Empty Nest Blessed!

Lemme give it to you straight: You can have the cutest clothes in the world, but if you don’t dress with confidence, you may have wasted your money! Dressing with confidence is about more than just the clothes you wear; it’s a reflection of your personal style and your very essence. If you want to dress with confidence, it’s important to be true to yourself and stay authentic to your personality and preferences.

Today, I’m partnering with The Mint Julep Boutique! I discovered them around the time I started working on our Game Day posts. (They have the cutest game day looks on their site!) The more I poked around on ShoptheMint.com, the more impressed I was. I’ve been dying to share them with you since I discovered them! (Read more about them on THIS “About” page.)

One thing I really love about The Mint Julep Boutique is the variety of items they carry! As an empty nester, I not only shop for myself, but I also shop for my senior adult mom (Who would love THESE earrings!), my 20-something daughter (Who would love THIS top!), my 30-something daughters-in-law (Who both need THIS sweatshirt!). Not only that, but The Mint Julep Boutique carries sizes for girls (7-14), so if you have granddaughters, you can shop for them at ShoptheMint.com, too!

All of the looks I’m sharing in this post are from The Mint Julep Boutique! The brand’s mission is to serve its customers by providing them with trendy and affordable clothing that makes them feel beautiful, confident, and present in their day-to-day lives! Their styles did that for me!

As always, click the pink text links or any image for more information. Everything fits TTS, unless I indicate otherwise.

Dress With Confidence

We all have days when we feel good about how we look and not so good about how we look. That’s normal! As women over 50, our bodies have been through a lot! There’s giving birth, caregiving, not to mention menopause! No one’s body looks like it did when they were 18! As long as you’re working toward good health, fitness, and strength, your body is heading in the right direction, and you should be proud of yourself. (I’m proud of you! 💗) Staying fit when you’re over 50 takes work, and I think cute workout clothes definitely help! 💪🙌

Call On You High Neck Cropped Tank (also in white) | Stick Together Scalloped Skort (also in white)

I think the key to dressing with confidence is to know who you are and what looks the best on you. It’s critical to let the very essence of you shine through! Your clothes should reflect your personality and your heart! Here’s what you need to remember.

1. Respect and Honor Yourself

Please, please, please respect yourself enough to get dressed every day! Even if you’re home doing housework or just running to the store. I hope you honor yourself enough to put on real clothes (You don’t have to get dressed up!) and a little makeup! I promise you’ll feel better about yourself and more positive about everything.

Also, you KNOW that if you don’t, your friend is going to want to drop something off “just for a quick second,” and you’ll have to scramble! 😄 (Been there!)

A good night’s sleep, a healthy diet, and regular exercise can all contribute to your overall sense of well-being, which in turn affects your confidence. To dress with confidence, be diligent about practicing self-care and making good choices!

The Mint Julep Boutique’s Staying In Red Floral Pajama Set

2. Know Your Style

Understanding your personal style and what’s flattering on your body is essential. What colors compliment your skin tone and hair color? What are your favorite features? What styles make you feel confident and most true to yourself?

Break It Down Dark Wash Flare Jeans (Also in petite HERE.) | The Slouchy Teal Blue Bubble Sleeve Sweater ( Click HERE for tons of other colors.) | Can’t Stop You Toast Brown Booties (Also in black.) | The Mint Julep Boutique Make A Statement Bundle

If you’ve been hanging around here for a while, you probably know that I like a variety of looks. I kind of dress for my mood! I think a woman who can pull off a wide variety of styles is interesting and fun!

The Dark Wash Flare Jeans I’m wearing above were kind of a stretch for me style-wise, but when I put them on, the flattering dark wash and stretchy, high waist pulled everything in and made me stand up tall!

Flare jeans look best long, so keep that in mind as you select a great pair this season. (I’m 5’5″ for size reference, and I’m wearing the regular size.) I love these with the tip of my Toast Brown Booties sticking out in front, but flares don’t have to be worn with heels, so choose the shoes you feel best in and go for it!

3. Wear Clothes That Fit Well

No matter what size you are, what size you used to be, or what size you’re aiming for, it’s important to wear clothes that fit. The size on the label doesn’t mean anything, and ill-fitting clothes can make you feel totally self-conscious.

After all, you don’t want to wear a dress that will make you feel like you have to suck in your tummy the whole time! Invest in shapewear, as well as tailoring or alterations, to ensure your clothes fit perfectly. When your clothes fit well, you look and feel more confident.

4. Build a Core Wardrobe You Love

Interesting women wear a mix of classic and trending pieces. Having a core wardrobe of well-fitting, quality basics will make it easier to work in trending pieces that make you look up-to-date and make you feel fabulous.

Beauty And Brains Cinnamon Brown Floral Blouse (Click HERE for other colors/patterns.) | Worth It Black Skinny Jeans | Can’t Stop You Toast Brown Booties (Also in black.) | Making Moves Beige Quilted Purse | Want It All White Beaded Bracelet Set

Once you have a great core wardrobe, incorporate trends that align with your style and make you feel good—but don’t sacrifice your comfort or authenticity for them. While it’s great to stay current, don’t feel pressured to follow every fashion trend. If you don’t like it, don’t wear it! (I successfully managed to skip the whole gladiator sandal trend completely! 😂)

5. Get Organized!

If you want to dress with confidence, you’re going to need to clean out your closet and get rid of stuff that’s no longer in style. (No, it won’t come in again any time soon! 🤣) Also, get rid of things you bought and haven’t worn in the past year (even if you paid a lot for them). Banish the out-of-date clothing, and send your guilt out the door, too!

Better Than Every Hot Pink Tennis Dress w/ Shorts (Click HERE for other colors.) | Making Moves Beige Quilted Purse | All About It Red Floral Earrings | Feeling Accomplished Gold Starburst Pendant Necklace

An organized, edited closet will show you what you need to add to update your style and help you spend wisely! Will some new workout clothes motivate you to move your body more? Are you in a club or a Bible Study each week where you’ll want to be sure you look cute? Will adding a new pair of booties or some cute accessories bring life to your style?

6. Plan Ahead

Take some time to plan your outfits the night before. I always do this! Sometimes, I even try things on to be sure I’m going to feel good in what I’m wearing! I’ve found that planning ahead reduces my morning stress and ensures I have time to get in my workout💪, quiet time 📖, and morning tea 🍵. (Which always helps my day go better!)

Romantic History Light Taupe Brown Ruffled Blouse (Click HERE for other colors.) | Break It Down Dark Wash Flare Jeans (Also in petite HERE.) | Can’t Stop You Toast Brown Booties (Also in black.) | Making Moves Beige Quilted Purse | All About It Red Floral Earrings

As you plan, consider the context of the day ahead. Dress appropriately for the occasion to avoid feeling out of place. If unsure, it’s better to be slightly overdressed than underdressed. (That’s my trick! I always try to dress up a little bit more than everyone else!)

7. Accessorize Thoughtfully

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The Mint Julep Boutique Make A Statement Bundle (Buy separately or bundle these and save!)

Accessories can make or break an outfit. Choose items that complement your outfit and personal style. Don’t overdo it; sometimes, less is more. Be sure you’re choosing the right shoes and handbag. I love these neutral booties and handbag below. They go with so much in my closet, making them a good value!

Can’t Stop You Toast Brown Booties | Making Moves Beige Quilted Purse

8. Learn From Others

Pay attention to people you admire for their style and confidence. Dissect their look! What is it about their choices that you find appealing? What can you learn from them and adapt to your own style?

Also, find brands that resonate with your personal style. I was thrilled when I found The Mint Julep Boutique because I think it’s an affordable one-stop shop for women in our generation who want to stay on top of the trends.

9. Own It!

Even if you’re feeling a bit unsure of yourself (“Will I know anyone here? Am I dressed right?”), good posture can make you appear more self-assured. Stand up straight, put your shoulders back, pull yourself up by your core, and walk with confidence. Make sure you’re smiling or at least have a pleasant, approachable look on your face. OWN IT, GIRL! 

Out In The World Dark Sage Green Ditsy Floral Midi Dress | Can’t Stop You Toast Brown Booties | Feeling Accomplished Gold Starburst Pendant Necklace

The truth is, there are places where people are going to look at you! Whether you’re walking down the aisle to find a seat at church or you’re walking into a restaurant, you need to exude confidence and assurance. People who do that are so attractive to others!

I always pause for a moment at the doorway, check my posture and the expression on my face, and then walk in like the aisle is my runway and I own the place! 😂 It sounds silly, but it works!

10. Confidence From Within

Remember that confidence isn’t just about appearance. It comes from within. As a woman over 50, you’ve accomplished so much in your life—and you’re not finished yet! You are so loved and cherished, and you need to know that and reflect that! When you feel and believe those things, it will be reflected in your style.

I’ve been wanting to write about this topic for so long! Many thanks to The Mint Julep Boutique for believing in what I wanted to share and providing me with so many darling pieces that let me illustrate what I wanted to say! (They’re pretty awesome like that!) Head over to ShoptheMint.com to check them out. You can take 15% off your first order when you sign up for their emails or texts.

Is dressing with confidence a challenge for you? We all struggle with it sometimes? I do! Give me your thoughts in the comments, okay?

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