While going through the first few steps of the “21 Steps to a More Stylish You” course, I’ve noticed many women have a hard time matching their clothes to their environment.
How much do you adapt your style, if at all? On one hand, you want to stay true to your unique style and personality. On the other, you might want to fit in more by dressing casually or in neutral tones. This balancing act is tricky, and I’ve already discussed the tendency to blend in too much in another article you might find helpful.
How Much Should You Adapt Your Clothes to Your Surroundings or the People You Meet?
It’s perfectly natural to tweak your wardrobe based on where you are or who you’ll be around. For instance, my style has shifted in every country I’ve lived in.
You might have noticed that friends often dress similarly, too. I usually consider who I’m meeting and might go a bit more colorful or artsy. When I met women like Sue Kreitzman and Diana Gabriel, I made an extra effort to embrace vibrant colors and prints.
Here’s an example: I wore a more colorful outfit than usual for a gathering, yet it included pieces from my wardrobe that I love. It’s a bit different but still true to me. For another event in LA, I wore something that really reflected my style—some asymmetry, vibrant hues, a statement necklace, and fabulous shoes. Most of us there chose solid colors with a lot of neutrals.
When I went out for dinner with Rosemond in Los Angeles, we both chose pants and tops, though I dressed a bit more formally. With Susan, who prefers a more neutral style, I didn’t fully match her look, but our big sunglasses and accessories tied our outfits together nicely.
Meeting Teresa, it’s almost uncanny how our outfits always align despite never coordinating in advance—even if the colors differ. It seemed like everyone got the memo to wear printed tops for a Style Club meetup in New York. During another meetup with colorful ladies Leslie and Dayle, I fit right in. Meeting Diana, although a coincidence, we both leaned towards similar styles, knowing she likes wearing black and white occasionally.
The key is not to become a complete chameleon. It’s about considering your surroundings and company while staying true to who you are.
How to Dress More Polished in a Casual Environment?
In very casual settings, it’s easy to blend in completely, but that might make you feel disconnected from your true self. For example, last week at a business conference mostly attended by men in t-shirts and jeans, I chose black or white cropped pants, a stylish top, and a nice jacket, accessorized with jewelry and some color.
Did I stand out? Absolutely. But I felt like myself and was confident in my choice. Sure, I toned it down a bit—not wearing the trendiest or most colorful pieces—but I still retained my style. Going too far in blending in would have made me uncomfortable and less confident.
How to Build the Confidence to Stay True to Yourself?
Staying true to yourself is a journey. At first, you might feel uneasy wearing a statement piece if no one else is. Begin with baby steps by adding small accessories in casual settings. Once comfortable, you can gradually introduce more colorful items.
People will eventually appreciate your effort and authenticity. If you’re uncertain about your true style or need help getting comfortable with it, my free 5-day “Find Your Style” challenge might be perfect for you. You can join here.
So, how much do you adapt your clothes to the friends you’re meeting?
