5 Tips for Wearing More Dresses and Skirts When You are a Pants Person — Inside Out Style

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Transitioning To Dresses And Skirts When You Always Wear Trousers And Tops

Reader Question: I would really love to wear more dresses and skirts, something more feminine in the way of clothing. I mostly wear trousers and mid-length tops because I’m overweight so I’m inclined to be self-conscious of wearing something different. I find it hard to dress up after Covid when you didn’t have to go anywhere. I also bought a bowler-style hat last year. I haven’t had the courage to wear it yet.





1. Have Courage

Often you feel uncomfortable trying something different or new because it is different from what you are used to. You can feel that you’re going to draw negative attention to yourself or even just attention which for some is uncomfortable.

Every one of us has style challenges. For you, wearing dresses and skirts is difficult. For someone else, they might struggle with wearing accessories or changing their hairstyle. And others will find dresses easy and pants hard!

By having the courage to try and potentially fail, you are learning and growing. You may even find something that really lights you up when it comes to your style. Jill Chivers has talked about this as she used to only wear two piece outfits until she met me and I talked to her about wearing dresses and skirts, and now she’s a huge fan!

2. Get Comfortable With Being Uncomfortable

While it may not feel like it in the moment, a little bit of discomfort goes a long way in terms of personal development, even if it doesn’t result in immediate positive feedback or reward.

Few people actually enjoy the feeling of being uncomfortable but it’s a big part of improving style. The challenge is to get past that initial feeling of wanting to return to the norm, so you can grow and benefit from that discomfort. This is why I love knit fabrics for dresses, like wearing a t-shirt but in one garment so I’m physically comfortable!

Transitioning from pants to dresses and skirts

When you get in a style rut, you find your comfort zone gets smaller and smaller. When you go out of your way to experience new things, or when you let new things happen to you, your body creates brand new neural pathways that fuel your creative spark and you begin to expand that comfort zone little by little.

I would really recommend that you do my Evolve Your Style challenge because you’ll be amazed at how fast you get out of your comfort zone. You will start looking at your wardrobe; your clothes and your style with new fresh eyes. I’ve seen remarkable changes in participants in this 31 day challenge in way less than the 31 days. You will be amazed at just how much more stylish you become and how you stop feeling so uncomfortable trying something new.

3. Baby Steps

Very often we feel uncomfortable trying something different or new because it is different for you. The best way to start is with baby steps, such as taking one step every day toward the direction that interests you. How does this help? It works because it gradually exposes you to a new experience. So try wearing the dress or skirt just around the house. Just wear it at home and it will become second nature when you’re out. Then wear it out to the supermarket or somewhere that is low risk. Notice how people don’t react negatively to you and this can give you the confidence to start wearing them when you go out socially or to work.

4.Get Curious

Do you have a supportive friend or partner? Wear the dress or skirt around them and ask them questions. This will help you realize that there are many different perspectives in the world and it’s okay to have your own.

The Evolve Your Style program has a Facebook group full of fabulous women who just like you have taken small daily challenges to improve their style. They post photos of their outfits, provide kind and considerate feedback; celebrate each other’s style wins. I’m constantly grateful for the encouragement and support they give each other as each participant moves through the challenges.

Dresses and skirts don't have to be formal - wear with sneakersRemember, your dress or skirt outfit doesn’t have to be formal, it can be casual – why not wear your dress or skirt with a pair of sneakers or a denim jacket to make it feel more casual if you have only worn your skirts or dresses in more formal settings before?

5. Embrace the Compliments

When you make changes to your style, it is natural to feel self-conscious. Other people may notice and you may get a few comments. These comments will be largely positive and encouraging. If you find it difficult to accept a compliment with grace, just reply with “Thank you.” You deserve credit for recognizing an opportunity to improve your style and acting on it.

You can look great at any weight. It’s just a matter of finding the styles and the clothes that work for you. So twirl in those skirts and wear the hat!

Want to improve your style? Evolve Your Style is a life-changing 31 day style challenge created using the latest brain science guaranteed to get you out of your style rut! This challenge gives you daily prompts that are baby steps to creating different outfits every day and putting all the knowledge you’ve learned into the program.

If you want to deep dive in and define your style, head over to the 7 Steps to Style program. 7 Steps to Style provides the colour, style and wardrobing foundations to transform yourself. You’ll create a fresh, flattering, and inspiring style that you will own and love. 7 Steps to Style encourages you to express your individual personality through your style and does not box you into a predetermined style category with rigid rules. As a bonus, the Evolve Your Style challenge is also included!

Further Reading

How to Develop Your Style When You Lack Confidence

11 Ways to Improve Your Body Image, Self-Acceptance and Your Style

Why Courage is the Ingredient You Need To Become More Stylish

Why You Won’t Become Stylish in a Week

5 Tips for Wearing More Dresses and Skirts When You are a Pants Person

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