Dresses For Grown-Up Women Who Want to Feel Confident
We’ve been inundated with puffy sleeves, gathers, ruffles, and tiers in tops and dresses for so many years that it’s hard to find alternatives when looking for a simple dress. For our Over 50 Style edit this month, Cindy and I gave ourselves a challenge…find a dress or two that spoke our personal style language that we would feel confident wearing. That’s been a tall order. Cindy and I agree that this has been one of our toughest posts to write.
My readers have requested more dress options lately so I’ve been trying them on for you at every opportunity. Here are some dresses I shared-
- Dressing Room Diaries- Prints at Talbots
- Beautiful and Modest Spring Dresses for Easter and Passover Celebrations
- Dressing Room Diary: Spring 2023 New Arrivals at J.McLaughlin
- Dressing Room Diary- What’s New At J. Jill
- Dressing Room Diary- Casual Dresses
I can conservatively say that I’ve tried on over 40 dresses in the last few weeks, trying to find a dress that rang all my bells. I began to feel like Goldilocks; one was too short, one was too loose, one had awkward sleeves, and on and on. And in the end, I had to compromise on a few things, as is usually the case when buying clothes off the rack.
I’ve had my eye on this dress for years. Yup, you heard that right, years. Eileen Fisher has been making this style for several years. I tried it on last year in black and loved it, but I wanted it in a color, so I waited for this season’s options, which did not disappoint. This raspberry tickled my fancy in a big way and had to be mine! I’m a big fan of its crushed silk, pleated fabric, which is reminiscent of my coveted Babette skirt. It skims the body but doesn’t cling, is a modest length, and can be dressed way up or down.
This type of fabric travels beautifully, and the silk feels so luxurious. It’s an investment for sure, but one I will wear for many years, making the cost per wear low. I have an upcoming bridal shower that this will be perfect for. I’m wearing it with hoop earrings that were a gift from my daughter, a long silver necklace combined with a charm necklace I inherited from my mom, and a treasured Renaissance cable bracelet that was an anniversary gift from my husband many years ago.
I prefer arm coverage, so I added this little linen and cotton cardigan, which matches the color perfectly. Along with great neutrals, I also discovered this dress comes in Atlantis Blue, which I ordered when Eileen Fisher was having their spring sale last week. This dress does have tiers, but they don’t feel juvenile to me because they lay flat.
I’ve always loved shirtdresses, and this cotton gauze one has a front tie that slims the tummy section without a separate belt. It rings most of my bells, and I’ve discovered it’s really quite perfect for me. It’s neutral (navy), has sleeves, and has a flattering V-neck. It’s almost sold out in solids but still stocked in a striped fabric.
I’m wearing it with my waterproof Birks that are super comfortable, and they’ve convinced me to invest in a leather pair along with this modern tote bag which Nordstrom Rack has finally restocked in blue. I snagged my straw hat out of a sale bin for $16 many years ago, and the Jenny Bird chain earrings are long sold out but on constant repeat in my wardrobe these days.
Is there a magic formula for finding a dress that makes a grown-up woman feel confident? There sure is. Start with the must-have features you require in a dress and are unwilling to compromise on. Then move on to fit and color. Does it flatter your shape and fit the occasion you need it for? And lastly, does it bring up negative vibes (like childish) that might spoil your enjoyment while wearing it?
How do you choose a dress?
Let’s check out what dresses Cindy has found on Cindy Hattersley Design.
I absolutely love the EF dress on you, the color is gorgeous! I also really like the blue gauze dress. Are you wearing a petite size in it?
No these are no petite. I hemmed the blue dress myself with a quick running stitch about 2”.
You look beautiful in every dress! I love dresses, and prefer them to pants. At the end of the day it is all about comfort and what makes you feel good.
It is all about what makes us feel comfortable. I totally agree, Elizabeth.
I love the Eileen Fisher dress!
If you decide to try some regular Birkenstocks you need to know that because they are leather they not going to be so soft on the foot until they are “broken in”….if the leather was not tough Birkenstocks would not have their reputation for lasting a long time. The foot bed is just what you need to support your foot issues. I am going to share a “trick” taught to me way back in the 70’s from a Birkenstock dealer when I bought my first pair of Birks and I have done this with every pair I have purchased. When you get a new pair of Birks put some shoe cream on the underside of the straps and make sure you cover the cut edge. Wear them around the house for a while….you may need to put the cream on more than once. Basically this does the same thing as what your sweaty foot does over time….just speeds it up so you can wear and enjoy your sandals. Birkenstocks used to be easily available in widths but now widths are mostly only available on their website….the correct width helps with comfort. If your feet are Narrow like mine you will likely find Mephistos more comfortable because they are more narrow. Birkenstocks are German…Mephistos are French and both are reputable companies that have been in business for years.
That’s a great tip, Lauren. Thanks for letting me in on it. I’ll pass it on to my daughter too because she’s trying to break a pair in.
The Eileen Fisher dress is gorgeous on you. I looked at the website when you announced the sale, but didn’t fall in love with anything. However, after seeing this dress on you, I would reconsider. Of course, now the sale is over, so I guess it’ll have to wait for a future sale. I really love the blue gauze dress. Unfortunately it’s sold out in my size. I have to say that you look great in the blue and white floral dress. Because it looked so great on you and since our coloring is similar, I ordered it. I always fall in love with garments in pretty much any shade of blue and thought this floral would be a great addition to my wardrobe. I haven’t bought a dress in quite a while. I was excited to try it on when it arrived earlier this week. But alas, it’s on it’s way back. I found the floral just didn’t look as good on me as it did on you.
I never wear dresses, but if I did I would love the blue floral knit that you modeled. You look fabulous in all of them though. Raspberry is a gorgeous color on you!
Love the raspberry silk midi and matching cardigan on you. The Atlantic blue will be great as well. That would be my favorite. Also, the only dry cleaner in my small town closed. 50 miles to go twice is too much. So I must but washable but many lately I hang to dry. At 5’2” I am a curvy petite woman. I did buy the grey twist dress and love it. However it really emphasizes my bust. My husband doesn’t like that unless I wear it only at home. Sigh. The knee length patterned blue dress is really pretty and looks like you could wear it everywhere. You did a great job looking for unicorn dresses.
Wow Jennifer !!! That EF stunning on you such an incredible color. So lovely when it all works !!
I am going to look at that further as a possibility for my upcoming trip this summer. For the Atlantic Blue version what would you suggest for shoulders? I love brands that offer petite sizes. I just bought a red dress from Faithfull the brand which is perfect for a bit of drama and a lovely restaurant night. Happy weekend friend xo
I ordered this lttle cardi and this wrap. Both in the Atlantis blue.
I like the blue knit floral dress and the navy blue gauge dress a lot. I really hate the EF dress. It just hangs straight. I think they charge a lot!
All of that trying-on sounds like a lot of work but provides some good laughs, at least it did for me. Thank you for this post! Will the inexpensive twist front dress add a lot of bulk to the tummy area? The dress is rayon, which shoots down from the shoulders. That always helps.