How to Step Out of Your Style Comfort Zone

I don’t dress the same way I did 2 years ago, let alone 10 years ago. One day I’ll want to wear an all black, creative look. The next I may want soft neutrals with a breezy feel. My style is always evolving so my comfort zone shifts with it.

Two years ago I would never consider wearing tassel earrings. I now own several pairs and enjoy their look. Jennifer Connolly of A Well Styled Life wearing tassel earrings

Everyone has a style comfort zone. Some women like to wear brightly colored clothes with lots of details and others prefer monochromatic with simple lines. One isn’t right and the other wrong. It’s all personal taste. But what happens when you get bored with your comfort zone and want to shake things up?

Start by observing what’s around you. Inspiration is everywhere from blogs to Pinterest to Instagram. If you’re looking for how other women put their outfits together, these are a great resource.

Start small

Accessories can be the least expensive and easiest ways to step out of your style comfort zone. The financial investment is small and you can wear them with your current clothes to see how they feel.

Take selfies

Looking at pictures of your outfits can be eye-opening. It’s completely different than looking in the mirror and a better way to determine if you like how something looks on you. You might admire and love a look on others but discover it looks wrong on you. Examine your images and see what parts feel right and what you’d like to change. If the shape of something feels wrong, consider whether you’d prefer it in a different color.

Listen to your instinct

Don’t force it but don’t give up early. If something feels wrong you don’t have to stick with it. Go back to the drawing board and try something else. Just because one look is not for you doesn’t mean a small tweak couldn’t make it work for you.

Personalize it

I’m a big fan of the power of alterations. If a new shape isn’t quite what you had in mind you can personalize it with alterations. Often a seamstress can tweak things enough to make them feel like you and get you moving in a new direction.

Several years ago my wardrobe was almost exclusively black with no pattern other than stripes. This summer I bought a colorful kimono with a floral print and I love it.Jennifer Connolly of A Well Styled Life modeling earrings from Artful Home

There are plenty of rules and lists of what we should and shouldn’t wear because of our body silhouette and coloring. The truth is these are all guidelines to use or toss at our discretion. The goal is to dress in a way that makes you happy, gives you confidence and feels authentic.

Is there validity to flattering proportion and color theories for women? Yes. But you needn’t be a slave to them at the expense of your creativity.

Is there a style you’ve wanted to try?

Thanks for reading ladies and have a great day.




  1. You are very wise and I like your style.

  2. I tend to gravitate towards jackets and mostly long sweaters to wear over my tops and pants. I find long necklaces really make the outfit complete. I also like my silver hoop earrings and bracelets. Also a nice handbag adds to the look. A nice pair of shoes compliments your outfit as well.

  3. Mary Alice Ahlgren says:

    Can you teach us how to take selfies of outfits? I’ve tried and haven’t been successful at getting them right.

    1. Just hold your phone in front of you, face the mirror and snap. You can look into the screen of your phone to be sure it’s lined up right

  4. I surprised myself this summer, when I bought a cotton knit top with fringe. I feel in love with it but thought this will sit in my closet, another unworn garment. Not so! I’ve worn it many times and feel fabulous in it. For a person that likes tailored, conservative clothing this was a big step. I guess I do have a flamboyant side. ????

    1. Wonderful! I love surprising myself. It sounds a bit bohemian which I’m also trying more of these days.

  5. I love the jeans ensemble. Is your scarf short or is it all tucked into your shirt somehow? Your hair looks great, too! I have been following you for several years and I have noticed your shift in clothing choices, especially adding a long third piece.

    1. The scarf is medium length and wrapped then tucked. That third piece can make all the difference.

  6. I agree about adding accessories. They are fun and do not have to be a major investment. By the way, your hair looks so good. Love the color. Is it highlighted?

    1. I did add some highlights. I’m not going silver fast enough. Go go figure.

  7. My grandkids were looking at some old photos and there were some with me wearing what I liked 30 plus years ago. I was a little surprised to realize I would wear the same things today, albeit in a different color or length. I guess my style doesn’t evolve much. The only thing really different is that I now wear more casual, drapy things than I did back then, before I retired.

  8. Jennifer, No earth shaking fashion comment but I did want to say…you look just adorable…I love every outfit that you are wearing…the white shirt in front of the purple flowers is fresh and sparkly on you…I love and appreciate the black with color….You know how I appreciate black and adding the touch of color is perfect…Thanks for sharing ….

  9. Hi Jennifer! I take away a lot from your posts, you always look so good. I only ever had a “office look” and have never had a clue what to do from there. Hope one day by continuing to read this, I will find “it” hahah!

    Take good care,

    1. I’m so glad you’re here. Please reach out if I can help.

  10. Jennifer,
    I lIke your suggestion about adding accessories to push the comfort zone a little.I mostly have the basics but I can see where adding more current accessories can give me that that pop that I am looking for.

  11. Excellent advice as usual Jennifer. I’m certainly dressing with more courage compared to a few years ago. It’s good to stretch our comfort zones. Gives us a new zest for life even when it’s clothes.

  12. Me again…love the hat you are wearing here. I’d like to find one like it. Always a challenge with my round face and baby fine hair. You look amazing and very happy in this photo!

    1. With a round face try to avoid round crowns. Look for contrast not similarity in shapes

      1. Thanks#

  13. This is exactly what brought me to blogs a couple of years ago. I was hoping for some inspiration but also to find others who, like me, knock down (or at least move aside) the barriers of age rules and restrictions to explore all the possibilities of fashion and living. I always knew “how to dress” but when I turned 50 I felt uncertain for the first time, disconnected from the images around me. You, and a few others I found when I googled have been wonderful inspiration and have provided a community that I wouldn’t otherwise had access to. I am also checking out Instagram now so I have access to people across the world. So wonderful to see!

    As far as style, I’m trying things on and taking some risks. The one thing I can no longer do is a monochromatic colour scheme head-to-toe. As much as I love black etc. I need pops of colour like leopard and fuchsia, at the very least in accessories. I’m not sure what I want to try next. I would like to invest in a new black blazer and a leather jacket, which don’t sound new but I’m just not sure what style yet since there are so much to choose from. I also find footwear and pant lengths complicated, more so since I am still working at a leadership level and need to look professional while feeding my creative style.

  14. Kathleen O'Brien says:

    My comfort zones have changed as I’ve gotten older. I’m pretty much an all black and white girl now. Maybe with a splash of color – but I seem to reach for black and white prints, and black. My tastes seem to have changed as well from when I was younger. Less is more to me now. And usually interesting shapes, such as angled, asymetrical or lantern.

  15. Catherine says:

    Cathy is so right, I will try on anything because really you don’t know until you try! I have a different problem then others. I wore blue and only blue in various forms for many years. I had my colours done in the 80s and that blew the doors open to wearing lots of colours. Now when I wear a simple monochrome look people comment or ask if I am alright, I don’t look like myself. I looked at your post and I want to do the all black with a pink scarf in the first picture. Funny that I think going simpler is stretching my comfort zone. I have all the elements of the jeans outfit, so I think I will copy that look too! Thanks for the inspiration

    1. Please ignore whatever color typing you had done which has limited your creativity. Our most flattering colors change with age and you may have been given wrong advice. I would love to help you get back on track

  16. Well the body changes and new things work now! I luv your advice on using accessories! Adds a twist without looking like I’m trying to be what I’m not!

  17. I’m always evolving, two years ago I wouldn’t wear anything fitted. Because I had just retired I felt I needed to wear my uniform of boring tees, mama jeans and tennies. In the last year I’ve embraced skinny jeans, leggings and stripes. I’ve discovered I like bargain shopping. If I see an outfit I’d like to try I take to a dressing room. If it looks and feels good in their horrible lighting it works.

  18. You look great as usual!!! I also used to wear black all the time, until my husband said it was boring. So, I started adding pink to my wardrobe. Then I tired of that and switched to navy blue! This year I added a lot of embroidered tops to my wardrobe. Re-added white and pink tops. I still have not bought any off the shoulder. My shoulders are too wide for them. I just cannot get into the tassel earrings. I feel they will be out of style soon. Before we retired, I wore a lot of scarves to add color and pattern to my outfits. Now, living in Florida, I don’t wear a lot of scarves so I had to start adding color.

  19. Hello from Canada Jennifer! Thank you for your posts. As a woman of our excellent age, I appreciate your ideas and perspectives. You always look fabulous and you inspire me to do the same. Would you share with me the source for the necklace with the name ring pendants? I would love to have one with my grandson’s and grandchild-to-be’s names.

    1. Hi Lauryn! I’m so glad you’re here! I don’t have any info to share about a necklace with pendants for names. Could it have been an ad on my site?

    2. Deborah Duncan says:

      Citrus Silver – a small Canadian company – sounds like what you are looking for. I’ve purchased several items from there and have been very pleased. Check out the website.

  20. You always look so great, Jennifer. I would add to your list to ask yourself what does this say about me…what are the messages it sends and see if those are the messages you want to send….then go for it if you like what it says!! I am wearing printed pants today and love them!

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