Street Style Inspiration for Women over 50

78 Comments

1. I love the street videos as they give me ideas on how to style outfits and to see real women. The first thing I noticed is the confidence in their body language and the second thing is that they are well groomed eg. hair is done. I particularly paid attention to women with my body type and how they styled wider pants. I also noticed their footwear and how it complemented their outfits.
   Thanks for the video and your new “format”.

2. Hi Pam, I echo Julie, love this new format! Very diverse outfits, lots of color and bolder outfits. I focused on the footwear as this is a huge challenge for me. Hoka sneakers (and ive tried a lot of brands) are the only shoe I can wear all day at work with any type of comfort. These women coordinate and make it look stylish. Really enjoyed the older gentlemen near the beginning in the white shorts, blue jacket and hat. I have a few “dressier” sweatshirts (from jjill) which I wear with scarves to make them look more polished. Have a great day.

3. So glad you enjoyed this, Julie!

4. Thanks Betty. That gentleman gave me a good chuckle!

5. Hi Pam, I am enjoying the street style videos; it’s a great opportunity to view European style. The speed of the video is perfect so accessories can be observed. I did notice that no one in London has embraced the “shacket”. I do not wear sweatshirts as part of my every day look- too casual. I am in my 50s and want to be part of Team Overdressed, not to be admired by others but for myself. Yesterday was a snow day where I live and I had a doctor appointment so I had to wear more suitable shoes for the weather. A woman in her 60s walked in looking as though her husband dropped her at the door: perfect attire!…(in my opinion) I thought of you and wanted to take her picture. We could start a new video trend called Waiting Room Style.

6. An aside…. I bought the book you recommended on health and aging. It has yet to arrive but I am looking forward to it.

7. lol!! I agree…sadly waiting room style is where we spend a big chunk of time as we age. But I have enjoyed watching women there. I love that you said Team OverDressed is for you! As it should be. Thanks Nancy!

8. I hope it helps and inspires!

9. I would not be on Team Overdressed, except that everyone else seems to be in pajamas, so I guess jeans, a sweater and jewelry qualify :). I noticed in the video how huge all the footwear was and how prominent because pants were so short. As an accessories lover, I have many chunky sneakers, but find myself gravitating these days to a sleeker style. I do not wear a “typical” sweatshirt except at home and working out. That said, I do wear an athleisure-style top or a “fancy” sweatshirt out. For example, I wore a sweatshirt/tunic-like top from Athleta called a coaster(does not have the typical banded bottom) to the doctor yesterday. I do like the striped/landscape sweatshirt on the right in the Dillards display and would wear that for very casual errands and the coffee shop, but the bottoms would be real pants or denim, not leggings or sweatpants. It’s all in the mix.

10. Hi Pam, the video was interesting and had a wide diversity of styles! Personally, I am a fan of the previous Wednesday news format. I loved all the different topics and always found lots to read and learn about. You are on my daily read every day!

11. I enjoyed the video this morning because I had the time to watch the entire thing. I was struck by the number of long, patterned coats, lower heeled, comfortable shoes, and patterned suits on women. I enjoy wearing color, and I would wear many of the long coats, but I wouldn’t be comfortable in those patterned suits. I also noticed how some people were touching, arms wrapped together with the person they were walking next to. Since my Mr. B and I usually hold hands as we walk together, I wondered if they did as we do because we each are not steady when we walk so we essentially increase each other’s balance. Plus I still love to touch him after 54 years. I did have my foot surgery yesterday in the middle of that bad storm which blew through the South so we had no power at times, and were under a tornado watch and could not leave. But you have been on my mind since I’m struggling with crutches, a scooter, and pain. I will be strong and hopefully feel better soon.

12. Pam, I really enjoyed the video. All the women, and men!, looked great. I didn’t think all the looks were for me but the confidence they exhibit is so inspiring. I love bright colours and it was encouraging to see how many ladies wore them. I was especially interested to see how many wore hats, I am a hat lover, and how many are wearing their hair naturally grey, like I do. I think the varied looks prove almost anything goes and we should use our instincts and go for it!!

13. Thanks Linda.

14. Thanks for sharing, Judy. I may bring it back occasionally. I am trying to offer what the majority enjoys. It is so helpful when you tell me what you like!

15. My heart goes out to you, Celia. I pray for little pain and comfort in recovery. Be good and don’t break a pin like I did. Stay strong!

16. I loved the video. I noticed how many women ( and men) wore bright overcoats in colors and prints. I have always worn coats and jackets in solid colors. Gives me something to think about!

17. I like this new format. That said, there are only a handful of outfits I would consider copying. Some were absolutely ridiculous and made me wonder if those women own a mirror. I did notice, those Londoner’s really love their sneakers. Not a fan of wearing sneakers with a really nice dressy outfit.

    I only wear sweatshirts when I’m going to the gym.

18. Well, that was fun to watch early in the morning! I noticed all the great crossbody bags; I have been acutely aware of keeping my purse close to me while shopping since I’ve personally witnessed 3 handbag highjacks in the last 4 months. I also noticed all the great coats; I gave away 40 coats when I moved to SoCal from NY. When I worked my coat wardrobe got a workout but out here it never gets cold enough for a wool coat. I own a few lightweight sweatshirts that I usually wear with leggings and sneakers. I am not a fan of hoods or banded hems on sweatshirts. I loved seeing all the flat shoes being worn as well.

19. Remember Jan, unique style to some may not be your unique style. I saw a little bit of everything in this video and congratulations to those dressing to their own unique style. It isn’t me either, but I love to see women enjoying who they are.
    Thanks for joining in.

20. There are so many coats I would love to own, but in South Texas would seldom wear…so I completely understand. But it is much fun to watch others styling winter outfits…whether I can wear them or not.

21. I saw more color in this video…more women, more women alone, more older women, some bodies that were not super slim. Maybe there was just a little less polish than Milan, which actually made me feel a little more comfortable. The thing that is most missing for me is children. Even at the upscale shopping areas I’ve been to on my American travels I see children.

22. Hi Pam–enjoy the street style, but as a Wisconsinite it is so far off my radar, I only last a couple of minutes. I do wish you had a link to the adorable sunset striped sweatshirt you showed in the Dillards picture. Sweatshirts are in my wardrobe–especially cute ones. I work at the local food pantry 6x month and they are perfect for cute, warm and can put up with messes if need be. Do you at least know the brand of that sweatshirt? I’ve been scrolling and scrolling Dillards to no avail! I so admire your journey–you have been so straightforward about dealing with the STUFF of life–be it the awful like the home invasion, the wonderful like your son’s wedding, the challenging about your foot problems. You are a stylish friend to sit and have some coffee with and I love that!

23. I really enjoy the street style videos. Its interesting to see the variety of styles. Some struck me as quite over the top but were worn with confidence and made me smile. I also noticed all the colorful and patterned coats. I know the photographer was looking for examples of style but even most of the people in the background tended to dress neatly. I also noticed the footwear. So many women wearing black heavy boots or puffy white “trainers”. I’ve read that motorcycle boots are in fashion. There were more than a few looks I’d like to copy so I plan to watch this one again with a notebook in hand. I think we in the US can learn a lot from European city style. As to sweatshirts: I have a few of what is now called athleisure-style from upscale lines. I tend to wear them in the studio as they are as warm as a sweater but don’t snag on things as I move around. I would wear some of the styles in the slide show but not the shirts on Dillard’s display. Even in a sweatshirt I need a style that is neat and tailored without any writing or picture.

24. Luv the new format. The skinny pant definitely seems to be out n Europe. Foot wear is great.
    I have noticed more sweatshirts worn by both young & older here in the Midwest. I do wear them as well.

25. I enjoy these street videos, partly because Denver has no such shopping district and very little style in general. Some of those outfits made me say, “Great look,” while others made me wonder what was she thinking! My favs were at 11 seconds, the black pants under a b&w checked blazer, and at 6:29, the white haired lady wearing black trousers with a red wool pea coat, beautiful. Loved all the faux (or real?) fur too!

26. Interesting, Linlee…you are right. Perhaps these videos are done when children are in school? Also, there are laws, real and unspoken, which discourage and prevent children showing up in social media. It is for the protection against traffickers and kidnappers.

27. Hi Mary…just refresh your page and you will see that I added a link for the sweatshirt. It is only available now in plus size but is on sale for around $27!! I also told you the brand and there are similar styles on their page. So sorry that I forgot to put in the link.
    Thank you for your persistence to know what it is….and your kind words.

28. I love how you wrote, Kathie, that they wore the clothing with CONFIDENCE….more about that tomorrow.

29. Thanks for joining in, Lee.

30. Thanks for telling us where you favorites are located in the video, Sharon. I am going to go back and look at them.

31. Love this street style! Beautiful blazers, tailored coats, stylish footwear and handbags. These folks dressed with intention and purpose. At :53, this is a great casual look with the peachy sweater. The couple are stunning where the woman is wearing hot pink and a green coat. Sweatshirts: my go-to look for being at home in the winter. Comfortable and warm for house chores, relaxing, doing projects. When I go out, I’m usually in the overdressed club. Thanks for the fun post. Pamela.

32. Thank you, Marcia…so glad you enjoyed it.

33. I have been enjoying these Street style videos too, and have discovered a few others. Because I’m a daily walker with intention and there are great safe areas in our smallish city, I get out to walk in all weather ( a few exceptions). I notice that in the videos the women are far more put together than I am. I notice stylish footwear and lovely coats or jackets where I walk mainly for exercise with perhaps a short errand thrown in (library return bin or drop off at the dry cleaner). I do include a pretty scarf or beret if the weather dictates but no one would ever include me in a fashion video. Lol.
    Another thing I notice about European women is the confidence they exude even on crowded sidewalks, even walking with dress shoes. I love my trainers!
    Celia: I do hope your pain subsides and you soon feel better!

34. I wear hoodies, but they have to be the right hoodie. If they have a nice drape they can look very sophisticated. A cashmere hoodie, jeans and a t-shirt is a very casual look but perfect for much of life (grocery store, etc). I don’t wear 100% cotton hoodies anymore because they don’t look nice and, frankly, aren’t warm enough. Somehow cotton hoodies always look lumpy to me.

35. Loved this video and also the one last week. I noticed that there were lots of fur coats and jackets … not a fan of real fur, though. However, there was so much style!!! I really like the looser, draped coats which still managed to look dressy and sharp. It was interesting to note the many stylish men. These seemed to be more higher-end neighborhoods so I wonder if other areas dress as nicely. Please continue to show these street style videos!

36. I love that they walk with confidence and desire that for all of us…no matter what we are wearing. Thanks Paulette…and also for the kind words for Celia. I know exactly what today is like for her…she needs rest and care.

37. I also love a nice hoodie. I have one that I love to wear because of the fit and design. Thanks for mentioning them, Mary.

38. Pam, I did love the London street wear video, however, where I live any of these beautiful clothes wouldn’t be appreciated. , I love all the gorgeous coats, and how confident these women were while walking and shopping….If I went to San Francisco a bit more, I’d have a more elevated wardrobe, (I live across the bay from SF). In my suburban area, it’s really jeans, sweaters, boots or tennis shoes. Yes these can be elevated and I do my best, but I am mindful of where I shop and dine. I’d say this video gave me inspiration, but I’d never ever wear big chunky shoes and short legged pants. I do love sweatshirts though, they are comfy, I did like the green hoodie sweatshirt, but not the patterned one.

39. Thanks Beth…I think we can be inspired and learn so much for watching them. Glad you enjoyed it.

40. I hope you just enjoyed watching how others dress in different places, Nancy. Of course, there are many many locations that will not look this way. However, I believe we can be inspired by their confidence and that can be a goal interpreted in many ways.

41. I personally love the street scenes. I live in a small casual lake town. In winter, jeans and sweat shirts are the go to outfit, even in business places; in summer, it is shorts and tees. I love the dress in this London street scene video. There were very few jeans, and everyone walked confidently. I loved all the gray hair, too. I retired five years ago and moved back to my hometown. I had been in the workforce in a large city, and we probably overdressed for today’s world, but I love that look and will continue to some extent here. Love to see what people are doing in larger areas.

42. Your new format is refreshing. I’ve enjoyed both of the videos. It’s interesting to see the bright colors and mixed pattern combinations. It makes me realize what a conservative dresser I am. I also enjoyed seeing the men wearing patterned vests under their suit jackets. The quality of everyone’s clothes was impressive but too expensive for me to dress like that every day.

43. As I watch these people striding along talking on their phones I’m amazed that there isn’t more street crime in the world. Because it’s not just in London that folks are concentrating on their phone conversation as they ambulate through shopping areas. So many shopping bags and purses easy to grab and run with. I hope this makes me more aware as I go out and about. As far as style goes, some very smart and chic looks. Some make you want to get to know that person better because their appearance says much about how friendly they are and somewhat about their interests or approach to life. I think as we watch these videos we should keep in mind that in cities like London and Milan and other large sophisticated cities—and particularly the areas where these are filmed in those cities—it’s all about appearance and these are not shoppers going to pick up the weekly groceries, but going out to be seen by many.

44. First off: sending well wishes to Celia for a speedy recovery! 🤗 Loved seeing this video. The men were so nicely turned out. A couple of lovely fur coats again today on the ladies. I love faux fur collars, cuffs, and linings, but have never bought a full exterior fur coat. Seeing both videos now kind of makes me consider the idea. I imagine theirs are real fur, but that would just make me feel sad. Anyway, I own one sweatshirt zip up hooded cardigan with pockets. It’s pistachio colored, cute, from Kohl’s, and I wear it back home after my water classes at the Y.

45. Good for you, Cheryll!! Thanks for sharing.

46. I agree…every day would be a stretch! Thanks Judy!

47. I caught sight of myself in a sweatshirt while I was out and about. I haven’t worn one since. It has to be a quality sweatshirt and you need to be 100% put together or you just look homeless.

48. I love the fact that you noticed how their appearance can speak to friendliness. That is why one of my style adjectives is “approachable.” I want to dress in such a way as to say…let’s be friends…not I am above you.

49. Thanks Connie!

50. Love this discussion. My sweatshirts number maybe 1 and it is never seen outside of the house. For my short chunky frame sweatshirts are usually overwhelming. (Usually just too thick.) I prefer comfy clothing that actually look like something I might wear on a quick errand. Interesting details are a must. Example: crossover hem, mock neck, Cowell neck, cropped to fit my short waist…. Etc.

51. These street style videos have been great to see “real” people out and about. It’s refreshing to see how well-dressed and unique people can be.

    Personally, I find sweatshirts too sloppy. I would much rather wear a long sleeve tee or a simple pullover sweater.

52. Sigh, makes me want to be there. I noticed chunky footwear, fabulous accessories and skilled pattern mixing. Also more pant suits than I have seen stateside. All in all, tres chic. Thank you for sharing the video. I am enjoying these.

53. I love the idea of interesting details being a must! Thanks for sharing Suzi.

54. Thanks Nancy…glad you enjoy the videos.

55. OK…I will join you Penelope…made me want to be there as well.

56. The people in London look a bit more elevated than the people I see in Denver. Less puffer jackets and more wool coats and fur-look jackets. I’ll be in London late this Spring but I will probably look more like Denver than London. 🙂

57. Be your confident best, Jean and you will have fun!

58. Oh, yes! Love this “Street Style” format. Like a good movie, I will watch this again and again to pick out new details everytime. Things I noted: color combos, pant lengths and styles, shoes, and hair styles. I recently purchased pairs of both silver and rose gold sneakers. Not only are they incredibly comfortable, I get so many reaffirming remarks. As for sweatshirts, before retirement and Covid, I would barely wear one on a camping trip. Now, I have ordered and do wear several that are stylish, similar to long sleeved t-shirts, but of a heavy sturdier fabric. They are so comfortable, compliment many styles of jeans, don’t need to be dry cleaned (as do good sweaters), camoflage my “bubbly midrift” and skim my “jodphur” shaped hips. Incidentally, yours is the first blog I look for in the morning when I check email. You speak to me when you post, Thank you. Wishes for continued recovery andI hope it is not too long before you can wear those darling shoes!

59. Me too, Paula!! Thank you for being here and for commenting on street style and the sweatshirts!

60. Fascinating video. I find I am drawn to the understated rather than those wearing layers of clothing — top, vest, coat, scarf etc. etc. I love the look of the classic coat in a bright colour worn with a simple sweater or shirt, pants, and shoes or boots. While there were people wearing sneakers, I was struck by how many women wore low-heeled boots or shoes or flat comfortable-looking sandals. And so little denim!

    I did love the various boho looks with embroidery, ruffles, long skirts, etc., but while I would have worn some of these looks earlier in my life, I don’t want them now. The exception would be the boho coats or jackets worn with something simple underneath.

    How dressed up people are in London! How wealthy-looking these people are! And how colourful compared to Paris! Great choice of video, Pam!

61. Thanks, Cynthia and for sharing what you liked.

62. Good afternoon. This is another fun video to watch. London style is quirky and fun. When I was growing up,style was British influenced. I wore poor boy sweaters, short dresses, textured tights. Twiggy and Mary Quant were hot topics in Seventeen magazine. I notice that many British women from other sites that I cruise wear more maxi skirts then Americans. Confidence does reign , and perhaps woman are more accepting of differing body types in other countries. I am really attracted to the long wool coats, the accessories, the colors. I was very inspired (again) to work on outerwear. I love the women with the sedate layer under a gorgeous coat. I love looking at the women with the colorful shoes (flat red pair, purple boots). I love wearing accent colors with neutrals or combining my colors in unexpected ways. That is a goal for me this year- explore some different styles and color combinations, hopefully more from my closet.
    Sweatshirts are very common in my beach town, and I don’t care for them, but I will take one to the beach so I can either walk or take the coolness on a windy day. My ears are very sensitive to wind and pressure. I notice that there are now cashmere hoodies and I just might try one on for the heck of it. I saw a women with one under a lovely jacket. The way she draped the hood over the back was quite attractive. Never say never!

63. Exactly…every time I say never in regards to a trend, I end up trying it. If I lived in a cooler climate, I would definitely try a cashmere hoodie! Great memories of British style, Twiggy, Seventeen Magazine, The Beatles girlfriends, big hoops, high boots.,,so much fun! Thanks Deborah!

64. What stood out to me was vast array of footwear. While most of the styles were a bit over the top for me, the lady in the green coat with the hot dress looked stunning. The white-haired lady in the read peacoat with the black trousers was the closest to my style. I wear sweatshirts & fleece at home, but when out & about, I prefer sweaters when it is cold. That is why I will spend more for a good sweater & less for fleece & sweatshirts.

65. Thanks Becky! I need to watch the video again and focus on the footwear!

66. Having done some traveling in Europe, you can pick out a North American traveler on any street. What I was drawn to in this video was in Britain wear a pair of pants that are not jeans, a button up shirt, a good blazer and carry a high quality leather purse. If that’s not your style a long oversized or belted coat preferably colour coordinated to your outfit, wide pants, a scarf and a high quality leather purse. I’d like to see next week’s video be one of well dressed women in a north American mall or shopping area ( not in New York or LA ). I wear sweatshirts for athletic activities, curling and hiking, but without logos or designs but with scarves. I do have a couple of blazer style jackets made from a heavier sweatshirt type material I would wear out to lunch with friends but not to an event.

67. Thanks for sharing, Linda. I have seen those jackets in sweatshirt material and like them! Great way to elevate casual.

68. These videos are fun! I’d like to see you do screenshots of several street style outfits and see what style adjectives your readers think of when they see them and/or what the person pictured is trying to convey. I have trouble choosing adjectives that describe my style and your readers thoughts might help me.

69. Great idea, Kate! That is something that will be easier when I am boot free. But I am going to work on a way to make it happen. I am here to help out any way I can.

70. Please keep this format and use occasionally. It was a real eye opener. The colors, shoes and flowing pants are an inspiration for me. I am well up in years and stay a little too conservative. Not these ladies! If they can do it-I can do it.
    I love sweaters and prefer to wear them rather than sweatshirts. Cashmere sweatshirts, Maybe.
    Thank You for this fun video. I enjoy your column and look forward to the next one.

71. Yes, Dotty! If they can do it…you can do it!!
    Have fun!

72. Enjoyed the seasonal mix in this video with favourite outfit being at 4.10 with the trio of women and the one with the fur hat/faux sherpa jacket, trousers etc. as a casual yet IMO, ‘polished street style’. On the note also for those who have an Instagram account (I don’t) they might wish to follow Grece Ghanem (a now 56 year old Lebanese-Canadian) who began her fashion influencer/modeling career by doing ‘street-style’ just as a hobby at first. Last but not least as to sweatshirts; currently only own three which I basically wear around the house during the cooler months because of their flannel-like lining. (Two of them have a fun Bo-Ho vibe because of their print that are tunic length (label Farm Rio) paired with leggings in various plain colors that work with them and the third being a relax fit plain zippered, polo collared one in a plain light gray (an Eddie Bauer brand). Also even though I consider them comfort/semi-active wear, I do not wear sneakers with them and choose flat footwear instead which I feel do bump the outfits up a tad. (Re the latter, JMO and to each their own.) -Brenda-

73. What a fun video. My top favs are the 2 ladies in the black leather leggings. Next is the hot pink dress with the green coat and green heels. Third is the wild print skirt with matching tights. I’d wear all of these. I noticed right away that most of these ladies had good haircuts. This video also made me even more negative on the topic of wide leg pants. I wear sweatshirts but not as dressy attire. Could that be possible, sure but I haven’t as yet. I am delighted that nobody in this video seems to have heard the term “age appropriate.”

74. LOL! Therese, what really is age appropriate?! I agree these upperclass people striding along to see and be seen have never minded age appropriate. I would like to see people striding in and out of the grocery store to see what middle class people are wearing in Europe. I live in rural mountain Colorado and they dress very casual in jeans, flannel shirts or sweatshirts, denim jackets not blazers in warmer weather. I was struck by all of the natural white and grey hair, but the much longer coats in many colors and all of the fur, faux and real. Here it is puffer coats, warm scarves and beanies. We all know what beanies do to our hair. Yikes!!! It is 25 degrees, blowing snow and I had a dental appointment! I wonder what many of these women of all ages would do with our weather conditions…. I thought that most were much thinner than Americans. It was a fun video to watch, after the dentist appointment.

75. I feel like I’m in the minority but I much preferred your earlier news format. It was one of the highlights of my week. I always found interesting things I would not encounter on my own. I especially liked the healthy recipes.

76. I am listening Cynthia…Thanks for letting me know.

77. I do love the new format too! My work is more casual these days so I have picked up a few of the two piece sets that have more of a sweatshirt top but I try to get the one that have more style and then pay attention to styling the whole outfit.

78. Thanks Missy!

Comments are closed.