What Would Help You Dress With Confidence?
Happy Thursday ladies. It’s a new year and I’m thinking of new ways we can collaborate. My goal here is to help you discover what works for your body and your lifestyle so you can get dressed with confidence. I’d love to help each of you individually, but that’s not practical or possible so I’m trying to come with the next best thing.
Here’s what I’d like to know:
If I could do something (one thing) that would make it easier for you to get dressed with confidence every morning, what would it be?
Would you be helped by a list of what to wear, when, and what goes with what? Sort of like a recipe.
Would you be interested in joining a paid private group with access to me so I can give you personalized help?
Would you like me to help you shop your closet?
If you prefer to answer privately, simply respond to the email this post arrived in.
Thanks for your help and be sure to wear what makes you feel confident.

Well, let’s see. You go over color, travel, casual, dressy casual, some dressier, hats, lips, nails, shoes, undies and even pajamas. How to try on clothes, how to see what’s wrong or right. You do so much already. Ok, I’m waiting for the eye shadow tutorial. ?. I would definitely pay for a special occasion. I’m the full time RVer, my every day life right now is extremely casual with extremely limited wardrobe.
I told my husband last night, when we build, I want a 12×12 closet with a love seat and a chandelier, mirrors for 360 view.
The recipe idea is very appealing.
I’m with you on that closet, Nancy! BTW, why are you in an RV? Fires? I wonder if Jennifer could help out with the “start from scratch” problem fire victims have to face. (Like me.)
Your posts have had the most valuable information for me of any I have read, and I look forward to learning something new, or being reminded of what is important for older women in this confusing fashion world. Your “looks” are classic, practical and stylish, and I have been adding some good basics that you have suggested. But yes, staring at a full closet and putting it all together is where I get hung up! So a recipe is a great idea if it helps to bring in all the pieces! And also working with more of a core wardrobe and knowing what to get rid of, so it’s not so confusing. I want to aim for the less is more idea! Maybe a theme would be helpful for those of us with a varying lifestyle? Like a day with the grandkids, lunch at the museum, trip to the doggie park, working in the garden, a western dance, rock concert, beach vacation, etc? Thanks so much for enriching our lives with what you do!
Would enjoy your idea of a recipe for outfits and shopping your closet. I am petite and always enjoy comments about lengthening our legs and where to lengthen our silhouette. I do enjoy shopping for clothes. I have a varied closet from thrift shops, department stores, etc. I have a relaxed lifestyle (retired), enjoy traveling and would love examples of such. I do not shop on line often as I live in Canada and we do not enjoy the same selections as our neighbors south! Love your blog.
I also live in Canada. I shop online at 1ere Avenue for Josef Ribkoff. They have free shipping and free returns worldwide. I am petite however (5’0″) and their models are tall and slender, so I return a lot of things because I just feel swamped. They don’t carry petite. Laura does have petites and you can shop online, but you have to pay for shipping and returns. Along with Nygard, these are my go to places to shop online. Laura and some of the Nygard brands have petites and I’ve realized that I really need to shop petites most of the time.
I like the photos you share, but like others, you are slimmer and less curvy than I am, so I would appreciate seeing different body types, but still petite. I enjoy your blog, especially as it is age appropriate, but long for more Canadian content. I loved it when you were up here, but you still seemed to shop American brands while you were here.
The best gift I’ve ever received is a full length adjustable mirror. I use it for an overall last look before I walk out the door. So many times I’ve changed something such as earrings, scarf, necklace etc. I even use it for my arm exercises.
I think a factor that makes me not as confident in my dressing style is that I have great difficulty finding clothes that are truly speaking to me with color. I’m a brunette with brown eyes and fair to medium skin color (cool undertones). Stores seem to have an abundance of clothes in very neutral, or warm tones. I look horrible in most of these colors or greys. When I do find a true, clear color for my skin tone the clothes are too trendy or revealing. I think it would be helpful on your blog to suggest or show some primary color outfits, and brunette followers give suggestions of outfits they have found either in stores or online. Thanks!
I personally would very much appreciate if at all possible Canadian stores being used sometimes. Love your looks but can’t try them on. Also need help with sweater/jacket lengths and pulling outfits together.
I look forward to reading you each and every day Jennifer.
I have enjoyed all your posts. I would not be interested in a paid service unless you came to my house..lol. I already enjoy what you do. I’m 65 and am pretty straight up and down, but carry my weight in my stomach so I always have to have stretch to fit my stomach?. I have so many clothes I don’t even wear so I do like articles are shopping your closet and comfortable footwear too. Keep up the good work, stick to your passion and do what works for you. When you do, you will always have followers. Xoxo
Maybe some ideas for outfit formulas or ‘rules’ to use. Like what cut of jeans looks best with flats or what type of bootie looks good with dresses. I have trouble making my current wardrobe work because sometimes things are just a little off and it makes a big difference in the outfit as a whole. Not sure if that makes sense…
I’ve come to realize that what looks good in the ad/magazine may not/probably does not look good on me. I don’t look like that model. Short, size xl and over 60. I rarely see clothes modelled on someone like me. What has been helpful is to find a ‘role model’ that looks more like me and whose look I like. For example, there is a weather lady who is quite short, maybe five feet. I see that she wears simple clothes, often in one colour and in proportion to her size. It occasionally works with celebrities, for example Judi Dench.
I would like to see more footwear options for those of us whose feet hurt. 🙂 I can’t wear spike heals, not matter what height. I am looking at Vionics, but I don’t know much about them and they are pricey.
Love this idea!!!
What a great idea. I love clothes and am happy to experiment, but I know a few people who find getting dressed each morning a chore (I think that’s why so many women my age just wear yoga gear all day.) I’ll mention this potential service to them! Xx
The reason I follow a few bloggers is to help myself know what looks good at my age, since The stores, magazines, and media, do not address this subject well. I would like more images of older women wearing clothes that look good. Swimwear on the beach, shopping / lunch outfits, casual at home wear, some easy formal wear, going to a wedding wear, Travel wear, you get the idea. I do wonder, if we feel invisible, if it’s because the magazines, media, stores, do not include us in their imagery ? We buy from Chico’s, no grey haired images, we buy from Talbots, no older women images…etc…. so… more images, is my answer.
I really like this idea. Maybe there could be a “what I wore to” topic and we submit photos of what we wore and an explanation of why and if it worked or not. This is on my mind as today I’m meeting friends for lunch, but due to weather conditions had to change my outfit to accommodate boots with heavier treads as it’s very slippery out. Needed to wear a heavier sweater to balance the heavier boot style. And I had so wanted to wear my new sweater and scarf LOL.
I agree ,, I liked chicos online because I could see a model walking and wearing the outfit now they don’t do that or use older models as much ..
..you can’t tell how something looks unless it’s on a body ..why I like your blogs and your advice …
ithink most of us want to stay current without looking too trendy or young and want ways to camouflage or flatter our aging bodies and how to accessorize in new ways . I did like your blog in wardrobe staples ..had to change my whole wardrobe from working to retired in last five years ..so I went looking for those staples and am purging things that don’t work
years .. so I went shopping for new white T-shirt and blouse ?
I am 69 years old and not confident at all. It has been quite a struggle for me for the past 19 years since my husband passed in an truck accident. I am retired because I was let go from my job because of a mistake that was blamed on me completely and also my age, I believe. I had been there 15 years. I would like to see how to dress more confident for at home wear and casual wear.
I’m so sorry you’re feeling so sad. My mother was rudely dumped by my father after 25 years and since they worked in the same office, she was mortified and worked sporadically about a year and quit. Finally, I convinced her to volunteer (at the library) one day a week and she slowly made friends and ended up with a lunch group every Wed and a small group of travel pals, became a docent at a museum. And the library loved her. Perhaps a volunteer gig would help. Personally I would start with an event instead of a full on commitment like she did
I would love a list of what to wear, when, and what goes with what. I love recipe ideas! I like the idea of shopping my closet too. These two kind of go hand in hand.
Hi, Jennifer. Thank you for asking for our input. One suggestion I have is to allow one of your followers to post (perhaps once a week?) changing room photos so that we could all “listen and learn” as you advise that person on the best looks and why. That way we could see all body types being styled.
Love this idea! Anonymous and with general info…. working vrs retired, vacation vrs everyday, that kind of info.
I agree! That would be very helpful!
Love that idea!
I love that idea as well
Great idea! That would really be helpful to me.
That’s a great idea!
This would be awesome! My problem is how to make what I have layer or work together. For example, what to wear under the new longer cardigans I’ve purchased. Great ideas! Thank you!
I love Bea’s idea and would be game for this approach!
Like that idea
I like submitting an outfit to the group and getting feedback on it! Multiple opinions help me!
Great idea! I would go for this.
Linda, that’s a GREAT idea! Maybe in a closed facebook group? Maybe not just outfits but a piece, like “what are some different ways I could style this”
I like this idea also – a myriad of opinions!
I would be interested in a paid private group, but it would depend how much it costs. I don’t need help every day, but every once in a while. I have a wedding coming up in September and I know I will want help with that. And at Christmas I was putting on a blazer that I’ve had for years and only wear around that time of the year and thought I don’t think this looks right, I wish Jennifer could look at it!
I’d love of list of basics. I go into a store and feel overwhelmed! I wear a lot of linen since I’m in Florida in the winter and the Cape in The summer. Enjoying you!
I was NOT happy with so many of my clothing choices and giving them away after a year or so. I realized because I LOVE an outfit on you I would buy it because it was sooooo ‘cute’ but something wasn’t quite right on me. (I always blamed it on my hair!!). Shape wise you are a carrot or a straight but I am a pear so I would like to see an outfit that I could ‘tweek’ to fit my style. I don’t want a closet FULL of clothes but the clothes I have I would like to LOVE!! I really enjoy your daily emails and look forward to them each day. I also don’t have access to ‘big name’ stores so would have to drive 2 hours away to shop. So I started to shop on line more…..primarily at Nordstrom because of free shipping. I’m more visual so like to see the outfits you show on yourself and then you tell us where we can purchase them. I would also like to see how you can change ‘up’ an outfit with several different tops to give a different look.