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.

 

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56 Comments

  1. I too am retired, in my 70’s, living in a cold climate on the Great Lakes. Everyday jeans and sweaters are a no brainer BUT going to the symphony, luncheons, museums, dinner, yikes…at a loss. Have no idea how to put clothes together. For instance, let’s say a blazer from years ago, is it a classic or out of style? How about trousers? Think I’m in a time warp. When I shop and ask a sales associate for help, she dresses me like a 30 something! Way out of my age group. Didn’t have this problem 20 years ago but now!!! Help! Carolyn

  2. I am still working so my focus is on business/business casual looks. I need help with choosing colors that flatter me and with accessories. I am open to paying for your advice but not sure I would want to be part of a group. It seems many of your followers are retired or only interested in casual looks.
    I also appreciate your makeup/skin care tips!

  3. My daughter and I have been working on my wardrobe. With her help, I have recently purchased some good basic items. What I need now is for someone to look at the things I’ve had for a while and tell me what to get rid of and how to put outfits together from the rest. After that, with a list of items to fill in gaps, I think I’d be set!

  4. Elizabeth says:

    I like this idea, like previous poster, I am a pear not a carrot…so I do love seeing your outfits, many might not look good on a pear shape. I have not found a fashion blogger who is mature and a pear shape. I feel that most fashions are made for those with no hips..

    1. I am also on the hunt for mature pear shaped bloggers.

  5. I don’t feel confident most of the time. I’m 5’1/2″ and feel most everything makes me look dumpy. I am in my 70s and retired. We don’t go out much at all. My husband has a 2nd job that he loves. I spend most of my time in casual clothes. When it comes time to go somewhere, I really don’t know if I have the correct things to wear.

  6. I learn a lot from your blog and apprecaite it. I would like to know what clothes look good on a tall overweigh 65 year old woman with a large midriff to conceal. I try not to buy expensive clothing and buy a lot of Chicos on sale items online.

  7. I like the idea of submitting an outfit to the group, but I follow a group that does this and they always tell the person who posted it that the person looks great even when they look terrible so I don’t have confidence in the responses. I submitted a picture one time and stated I wanted honest feedback and I did get some feedback which was helpful.

  8. 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.
    -Brenda-
    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?

  9. 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!

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

  11. 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!!!

  12. 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?

  13. 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!

  14. 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.

  15. 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!

  16. 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.

  17. 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!