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- Whatās 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’ve also had my eye on that EF silk dress for a looong time, but the lack of petite (I am 5’2″) and cost has paused the purchase. I would also need to invest in a coordinating topper (a linen knit cardigan!). Can you please comment on the fit across the bust and armholes and waist in your Small? I am 34C, 135ish and was considering S vs XS.
Jo, I could have just about written your post! Jennifer, I’d love to hear your comments on this. Thanks ladies!
Iām 5ā2ā and have the EF silk dress in black. My alterations person was able to shorten it without destroying the proportion of the tiers, if that helps. It is a great versatile dress that I will wear for many years. Iām considering another color. They didnāt offer the beautiful raspberry or blue when I purchased the black.
I weigh almost 8lbs more than you and wear a 36b bra. The small is perfect but I might have been able to wear an XS.
I am about the same , I wear xs, I measure 33-34ā bust, and have small shoulders.
Love that silk midi dress with matching sweater. Beautiful color.
Thanks Lin
This is a fabulous post…there I said it. Hands down the Eileen Fisher dress is my favorite with the Caslon gauze number a close second. I think what we both discovered is there is a reason we don’t wear much pattern. This was a tough one for us but we muddled through!
Iād much rather wear texture than pattern. I think you look amazing!!
Wow, such a beautiful presentation – like artwork! Thanks for brightening our day with gorgeousness š¤©
For years Iāve looked for a black summer dress that doesnāt show too much skin. At 61, Iām ok with a lower neckline OR sleeveless, but not both, which seems too revealing now. I bought the front twist maxi dress youāre wearing because it fits my criteria. I also bought a dress from Walmart (Sofia Vergara eyelet empire dress). It has elbow length sleeves but is low cut. It was only $36, so I figured it was worth a try. Summer dresses are hard because the dress is the ENTIRE outfit, so I have to feel confident in it before I can accessorize and feel good about wearing it out.
Those are great points. Iāve gotten more modest with age donāt like to reveal as much.
Love, love, love the Eileen Fisher dress. I’m thinking of buying the blue dress and sweater. It looks so perfect for so many occasions for years to come. Thank you for this post on dresses.
Like the other short women, I find dresses that are just past knee length look best on me. I am loving the longer summer dresses though. As someone said, the EF dress looks spectacular on you, and since you can afford it, that’s great. I think I (we?) have to be a little cautious about ‘investment’ pieces: we won’t have the same arms, neck, and height 10-plus years from now. Since EF is organic, though, her clothes can be consigned or donated when we’re past wearing them and will still last for years — just on someone else.
And neither the EF or the gauze dress come in petites. Otherwise, I might think about it. But I can’t justify the price knowing I’d have to alter which might change the look too much.
I love the raspberry, silk midi dress! And you look stunning in it by the way!
So glad you found the dress you wanted in raspberry. It really looks great on you. Thanks for trying on so many dresses. I rarely wear them and when I need to I try to just wear one I already have. I’m just not a dress person. I think it has to do with only being 5’1. It’s hard to find petites that fit.
Petites are a challenge and they just shouldnāt be. Thank goodness for retailers who recognize women come in all shapes and sizes.
Those dresses are perfect for you Jennifer. The majority of dresses I’ve bought in my life have been “dressier” as I’ve always preferred a skirt or pants for a casual look. I’m challenging myself to find a casual midi, linen dress for this summer. Probably in blue or perhaps fuchsia, short sleeves, loose style and perhaps pockets.
Youāve just described the perfect dress and my hunt continues. I want all those features too!
Thank you for trying on all these dresses for us! The raspberry dress is spectacular but beyond my budget. Im sure youāll get a lot of pleasure wearing it. Iām glad you included the very affordable dress from N Rack.
That Nordstrom Rack dress is a great one. I love it.
I am noticing dresses this spring are looking retro – reminds me of silhouettes from Voque and Butterick vintage patterns. Iām liking how they look – Calvin Klein has quite a few and I saw one by Ralph Lauren that I really like but didnāt have my size. One reader commented on dress length and shoes – Iām confused as well. Not sure flats go well with midi dresses however being retired for 7 years and making flats and flip flops my go to, I have gotten out of wearing any heels kitten or stilettos. I do like shirt dresses in both knee length and midi.
That raspberry dress and cardigan are worth the investment! You can wear that dress in five, even ten, years and it will look new. And it is suitable for all occasions. The dress truly is the Goldilocks of dresses and it looks beautiful on you!
Thanks, Melissa. I hemmed and hawed about it because of the price but I know Iāll be wearing it in 10+ years so my cost per wear will be worth it!
Happy Friday Jennifer, the blue printed dress looks great on you.
Nice options with your dresses to try on. Hope the storm in your area didnāt damage your home. Have a nice weekendš„°
I JUST got that pink dress in black. Now I’m thinking I should have gone with a color. It is a ridiculous splurge, but with a trip to Italy coming up, I feel like I NEED it. š š It looks gorg on you!
Thank you my friend. The black will be stunning on you! Itās simply perfect for travel and will be so chic in Italy.
Being short, 5ā2ā, I need a petite size. If I find a dress that looks good on me but not petite, I have it altered. I try and stay with knee length which I feel makes me feel taller. To me, midcalf, is the wrong proportion for my body. Love the dresses you have shown us. Thank you!
That Eileen Fisher pleated silk midi dress is spectacular. Unfortunately so is the price. A little too pricey for my budget, but I love it and you wear it well.
@Jennifer: My sentiments is the same as Jan”s and sadly its even more expensive in Cdn. $$$$ …. š²…. but it is very tempting …. š. -Brenda-
If I were a dress- wearing woman I would insist on knee length, classic style (similar to shirt waist or coat style) in any color that flatters. As with most of my clothes I must try on. Midi or mid calf styles look dowdy on me and shoe styles with midi is baffling as well. I just avoid that length when possible.
The holy grail of dresses must have sleeves and be midi length. It must not be see-through. The shape will be A-line. I think you’re wearing it, in blue gauze.
The raspberry silk dress and sweater look stunning on you, Jennifer. Stunning! So glad that you made the investment. I also like the navy gauze shirt dress- not just for vacation but for a hot day.
I agree! Iāll wear this navy dress all summer long. I wish there were more colors!