How To Dress With Confidence & Wear The Damn Dress

Wear the damn dress

Sometimes we’re too close to the situation to really have perspective on what looks good because we’re so in our head about whether it will look good to others. We forget to look inward and listen to our feelings. If it FEELS good, it LOOKS good. Because you radiate that energy. Being a Personal Stylist, I see this a lot in clients. Sometimes they need me to remind them to just wear the damn dress! Let’s talk about how to dress with confidence.

If you run into the problem of not knowing how to dress with confidence for your body type and you often feel like nothing fits right then this is for you. 

We all feel this like sometimes. You feel like your legs are too short, your waist is too wide, your arms are too big, and your butt is too small. Seriously – as a Personal Stylist I’ve heard it all from both men and women regarding body image. When clothing doesn’t fit right, we blame our bodies when the clothing options are the problem.

Most people feel like there is something wrong with their body shape and that they won’t be able to find clothing, but I’m here to remind you that no perfect or ideal body exists. Every person’s body is unique; that’s what makes you, you! 

When a client feels discouraged about how they look, I want to do everything I can to show them that their body is perfect the way it is, and finding clothing that fits well makes all the difference. I remember working with a client with beautiful Michelle-Obama-like arms; she definitely did her push-ups but didn’t feel good about them. She had a smaller chest and felt her arms made her look too masculine, so when we worked together, I found short-sleeved options that complimented her arms so she could feel confident in her tops. 

Finding out how to dress your body has more to do with becoming aware of your own body’s uniqueness and less with following a body type chart. I know having a cookie-cutter plan seems more manageable than getting curious and specific to your own needs. 

If dressing yourself has been a challenge lately, I want you to remember:

1. Accept your body 

Accepting your body doesn’t mean you love every part of your body because the reality is that working through your body image is a lifetime process. Accepting your body is seeing it for what it is without judgment. It’s saying, “My pants are tight because my waist got bigger, I need to find a pant that fits well instead of torturing myself for why the pants are too small.”

When we don’t accept our bodies, we go into a spiral because we want to keep dressing as we did years ago. We go back to wanting to wear our favorite 10-year designer jeans or expensive dresses. But why would you want to make something work that doesn’t? Why would you try to fit into something from your past when you’re in a different place anyway?

Dress your body for where you are now. Don’t feel you have to be 10 pounds lighter, get the tummy tuck, or a personal trainer. What if you invested in yourself today to feel better and continued doing the work with time if that’s a big goal for you. I’m not saying at all to stay comfortable if you aren’t living in a healthy place; I’m saying that you can take care of yourself right now and once you lose the weight, update with new pieces again. In that time, you might feel differently about your style and body and switch up what you wear.

2. Find out what doesn’t fit your body anymore 

Your closet has the answers for you; it’s the key to finding out what you need to stop and start wearing.You want to look for clothing that makes you feel good when wearing it and not self-conscious; it should fit your body and take you effortlessly throughout your day. No pulling or tugging included. Look in your closet and find what you have to let go. Ask yourself questions like, “should I stop wearing mid-rise jeans because they feel funny around my waist?” and be ok with adapting.

When you edit down your closet from pieces that don’t serve you anymore, you’ll find space and possibilities to fill it in with things that feel good to you. When you keep items in your closet that don’t fit your body, it’s a constant reminder that your body has changed. 

This closet maintenance is done every six months to a year to ensure you keep it condensed to clothing that fits you best. Along the way, you might make some purchases you love and some purchases you tried out that didn’t work. It’s always good to go through with a fresh eye to decide what feels best to you and fits well. What you wore most and why and what you’d like to never to wear again (well, never say never, styles come back!) 

When working with clients, I take notes on everything! Why something doesn’t fit well, what does fit well, what pieces they like, what colors light them up. I call this The Style Tracker, which is available for you to purchase. It’s the best way to stay organized on what to avoid and look for later when you shop. The Style Tracker is a worksheet that you can print and take notes on anytime you try on pieces in your closet, new purchases you make online, and in the fitting room. It gives you a place to keep all your notes together to make your style discovery clear. You can purchase The Style Tracker here

3. Find 3 new pieces 

After you’ve gone through the process of accepting your body and search through your closet to find out what works or doesn’t, it’s time to shop! Instead of buying one new piece, purchase 3-5 to mix and match with clothes you already have and put an outfit that works together. Try on clothing in the correct size, don’t try to make certain styles or brands fit if they don’t, move on and work through items that will better suit you.

It’s so important to listen to my clients’ insecurities and make sure they know just how perfect they are where they’re at right now. I find suitable styles, colors, and cuts that make them forget about any imperfections and see themselves in a new light. One of my client’s had twins and was going on vacation with her husband, and she was dreading finding a swimsuit for the trip. The first one I pulled out for her ended up being the winner, and she couldn’t believe it fit her perfectly. I reminded her that her body is perfect just the way it is, and finding clothing that fits it makes a huge difference. 

When you do go out and venture on your own, don’t be discouraged by pieces that don’t fit well. Don’t give up on trying something new. I promise you there’s clothing that fits you right, and it takes a few tries. If you keep track of what you try and what doesn’t work, it makes the process easier.

Don’t give up on trying something new. I promise you there’s clothing that fits you right, and it takes a few tries. If you keep track of what you try and what doesn’t work, it makes the process easier and allows you to dress with confidence

Growing up, I struggled a lot with accepting my body, and as an adult, I’ve done more work to accept myself wherever I am. My body fluctuates with the amount of work I have in my life; it has changed with each decade, shifted after having my daughter, and will continue to grow and change with me as time goes on. And that’s ok!

I’m passionate about the topic of dressing your body for the way it is but also dressing your body in pieces that make you happy. If the dress makes you happy, wear the damn dress. I hope this helped you understand that “how to dress with confidence” really is all about how you feel on the inside and how you talk to yourself. You’ve got this!

I’m here to help you on your style journey. If you have any questions for me, you can send them to; I’d love to hear from you. Don’t forget to listen along to the podcast or watch along on YouTube too! Start a conversation with someone you love about your body, and share this blog if it resonates with you. 

If you want to get on the waitlist of my online program, go to, you are taken step by step through finding your style, where to shop, and building outfits. Plus, you get a personal shopper along the way to help you.

Build a style and wardrobe that truly reflects you.


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