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.



  1. Some excellent ideas/suggestions here Jennifer but something I feel that may be helpful/productive to your readers is your input as a stylist on the featured outfits of ‘Would You Wear It?’. This could be done as a followup with a breakdown of each piece as to its suitability for body type, an individual’s coloring, lifestyle, occasion etc. etc. etc. including accessories to be worn with it (as in footwear). Possibly it could be done in recipe/chart form and even printed off by your readers for guidance/reference purposes. All said, just a thought but shall add I agree with Lily above to ‘ take note when you feel fabulous in an outfit’ as there is more than one reason why you do.
    P.S.: Do hope you are over your cold Jennifer and feeling better.

    1. That’s a great idea. Usually only a few likes the outfit in Would you wear it. I always wonder *why did Jennifer select this?* I wish she would tell us?

  2. Nancy Olson says:

    I have an unusual shape (apple – very thin legs and behind). This makes it quite difficult to find clothing that looks proportioned and I am so tired of wearing jeans that are not flattering.
    So, yes – I need all the help I can get!

  3. Love Bea’s idea! Group-think + team effort!

  4. Laura W Rutledge says:

    Jennifer, I also wanted to ask you what you think is the best way to organize your closet? (I have an Ebay store selling clothing, and I pick up a lot of nice classic name brand clothes for a steal!) I stand there in the morning looking at all those pretty sweaters, button downs, etc., everything looking so nice together and organized. But, that’s not how we wear them, and I’ve forgotten (lol) what goes with them or what combinations worked and how I liked to wear them! I can see it helps to separate tunic tops, long sweaters and leggings, but I feel like I’m missing something. Maybe I should put an outfit together and organize my closet that way? Or maybe put things I wear toward the front and things I don’t wear would fall to the back? Take pics of my fav. outfits or looks & what, tape them to the mirror for when I’m half asleep in the morning and can’t think? Help!! And thanks!!!

  5. Thanks to you, I dress with confidence most of the time, especially for the day-to-day things. You’ve taught me a lot and often enlightened me on new products and tips. Fifteen years ago I was lucky enough to have a coworker who could have been your twin once come to my house, go through my closet, toss the bad pieces and tell me what works and why. She informally did my colors and taught me how to shop as a “winter” and about classics and fit. You keep me updated and adding to what I started!

    My lack of confidence comes from special occasions – not necessarily fancy ones. I always seem to be missing something. If I get a great new dress and I have the right shoes and accessories, then I realize I don’t have the right coat or jacket. I’m reluctant to spent more on getting something that works with that dress. Or let’s say I have a nice pair of shoes that goes with the nice dress and then I end up at an event that will have dancing but I can’t dance in those shoes! Suddenly I’m schlepping a tote bag with a second pair of shoes and feel insecure changing into shoes that don’t work with the dress.

    I guess I get caught without the right apparel at least once/month for a few occasions that don’t warrant a spend for the few times I’d wear them. They’re all different. Another example, I have a great short waterproof rain jacket because I’m usually going by car. But when I visit a city, I could use a long raincoat to go over dresses and nice pants because people dress differently in the city and I’m walking a lot in a downpour. Everyone else looks chic in their nice trench coats…I look like the sporty suburbanite.

    It’s hard to decide when to spend the money and fill the closet with pieces that are used only 2-3 times/year. I imagine that style bloggers have very large closets with the right thing for every occasion – and classic pieces that last many years through all the fashion trends.

    How do you find once-size-fits-most pieces that solve these awkward occasions?

  6. Marsheila says:

    Hi There, I love clothes and have a closet full of them; ranging from leisure to dress up. I think the recipe idea would be awesome. I am 62 and I like stylish clothes, but they must be comfy. As much as I would love for you to go through my closet; I am not sure you could handle doing that for me and everyone else. You have been giving me tips for years, and I Thank You!

  7. I think dressing with confidence is quite simple. Take note when you feel fabulous in an outfit. Those looks become a blueprint for building a wardrobe. Confidence comes from within. Like Sharon says above, a full length mirror is invaluable.

  8. My favorite articles by far are your “Dressing Room Diaries” with stores like Talbots, J Jill, and Chicos that feature petite sizing as well as plus sizing. What would be fun to see would be if you could encourage friends or other shoppers of different sizes to pose with you in outfits that look good on them and fit their lifestyle. I realize that this would involve more time with release forms and such, but it would be such fun. Thanks for all you do!

  9. I live in Canada (not a big city) so a lot of the clothing items shown are not available here. I have ordered from Nordstrom and other US retailers but sometimes with the shipping, duty, exchange, etc the cost is double what it is on the website.

    I would like to see cold weather coats, boots, gloves.

    The main problems I have in dressing is how to wear booties in cold weather (with no skin showing), comfortable flats and sandals for plantar problems, which jeans and especially tops suit an hourglass figure.

    I do get to the US every couple of years. I check websites before I go and make note of the items I’m interested in.

    I do enjoy the information on your website and try to find similar items in stores in my area.

  10. I am almost 60, but don’t feel over 40?. I would like to find someone who would style capsule wardrobe plans for women in the over 50 category, as I love to subscribe or purchase those capsule plans, by it sometimes feel that the styles and store they recommend don’t quite work for me. I’d love it if a stylist would create seasonal wardrobe plans for our age group and one that offers a variety of price points, too! I love your blog and appreciate all of the great advice you already provide!

  11. 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.

    1. 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.)

  12. Laura Rutledge says:

    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!

  13. 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.

    1. 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.

  14. 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.

  15. 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!

  16. Jill Fray says:

    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.

  17. 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

  18. 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…

  19. 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.

  20. 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.

  21. Trish Wilson says:

    Love this idea!!!

  22. 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

  23. 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.

    1. 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.

    2. Susan Mcbrine says:

      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 ?

  24. Dianne Lucas says:

    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.

    1. 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

  25. 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.

  26. 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.

    1. Love this idea! Anonymous and with general info…. working vrs retired, vacation vrs everyday, that kind of info.

      1. Nancy Stewart says:

        I agree! That would be very helpful!

      2. Love that idea!

      3. Maggie Morris says:

        I love that idea as well

    2. Great idea! That would really be helpful to me.

    3. Barbara K. says:

      That’s a great idea!

    4. 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!

    5. Connie Haines says:

      I love Bea’s idea and would be game for this approach!

  27. I like submitting an outfit to the group and getting feedback on it! Multiple opinions help me!

    1. Great idea! I would go for this.

    2. 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”

    3. I like this idea also – a myriad of opinions!

  28. 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!

  29. Joyce Reardon says:

    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!

  30. Rose Oelberg says:

    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.

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