Would You Wear It Halloween Edition with Pamela & Jennifer

Would You Wear It on Halloween on over 50 feeling 40

Happy Halloween to those who will celebrate, and welcome to Would You Wear It with me and my friend, Jennifer, with fall clothing displays.

This is the day we post fashion displays which have captured out attention and make us wonder what you would think of the styles. 

Would You Wear It on Halloween on over 50 feeling 40

I confess that I decided to share this one because it fit the Halloween color scheme with an orange and black style.   But please look it over and explain in detail why you would or would not wear this look.

Keep it personal and please do not comment in such a way that you insult someone else who feels differently from you.  

But, explain constructively in order to help other women understand why some styles do work or don’t work for certain body types, lifestyles, colorings or ages.

My look today features a black faux leather skirt…just in case you wondered!

Would You Wear this look at Dillards

So, ladies, give this your best stylist eye and tell us……………………………………………………………………………………………..


Full Moon on Halloween for Over 50 Feeling 40

Remember two things about tonight….it will be a rare full moon on Halloween, and for many of us, we gain an hour of sleep and fall back with the time. Don’t forget to set your clocks.

Tomorrow, I will officially kick off the holidays on Over 50 Feeling 40 with a special announcement...so make it a point to come back here!!

Now, tell us what you think, then go visit Jennifer at A Well Styled Life….and make sure tonight you


Shopping?  Please consider using these links and if you don’t see the brand you need here, ask me about it!





Eileen Fisher






Nordstrom Rack






Rack Room Shoes

J Crew Factory

Eloquii (for Plus Size)

GOLI on over 50 Feeling 40

For everyone who agrees with me that Apple Cider Vinegar is great for the metabolism and other health benefits, then order your GOLI today.  Just go to my page at GOLI HERE.  




  1. Happy happy Halloween Pamela! I’ve been sitting here with my coffee looking over these mannequins, and have decided that neither works for me. The long pleated skirt on left is not my style at all. I don’t care for longish skirts, nor pleats.
    The top would look awful on me. I see the top on a taller woman with long arms and an overall slim shape. The look on the right just wouldn’t work with my age, though if I were young, I’d pair that skirt and top with tall boots. To be honest, the today ME is a more classic, preppy dresser so I’d walk right by.

    1. I have a long black knife pleat skirt and it’s one of my favourite pieces. Not keen on the pleather but that’s a personal choice. I like the shape of the sweater, particularly the sleeves, but I look awful in orange.

  2. While I probably wouldn’t go for a faux leather pleated skirt, but I find the color combinations very inspiring. These tones can easily go into Thanksgiving -leave the black pointy hat at home. I also like the spare lines of the sweater.

  3. I wouldn’t wear the long skirt since I’m so petite., It would wear me. I like the short skirt, again since I’m so short it would be knee length! The orange sweater is gorgeous if the sleeves aren’t to wide I would definitely try it on. Orange is a great color for me.

  4. Happy Saturday Pam! I like the peach/orange top very much and would definitely wear that. The neckline is low enough to be flattering even though it’s a crew neck (often they don’t do me any favors unless they dip a little lower). The sleeves are interesting, the color is gorgeous, so yes to that. I do like pleated skirts very much but would pass on this one due to the fabric. Just looks too over the top for my taste. I like the style of the two piece, and with the right jewelry it would be very pretty. The other one with the short skirt, that’s a no for me. I don’t like the neckline on the top, nor do I like the print, and the skirt is much too short. I do love a pencil skirt, but no more mini skirts at my age. I wore them in the 60’s and 70’s, but that was then and this is now! Have a great weekend! I’m going to meet my son’s and daughter-in-law’s new puppy this afternoon and I’m excited!

  5. I would stop and think how I might change the look to suit me. I don’t wear that colour and the drop shoulder is not great on my slightly sloping shoulders. The skirt would accentuate the tummy area I would prefer to keep flat but the length is great. This type of display does make you stop and think what would I have at home to do a similar style. I would also add tall flat boots and either a large statement necklace or scarf tied artistically. Happy Halloween and looking forward to tomorrows post.

  6. This doesn’t appeal to me. I’m not a fan of pleated skirts on me and the orange color is very unflattering on my skin tone. I’d walk right past this display.

  7. The first outfit is a no for me. The drop shoulders and funnel sleeves would not suit my petite but not tiny body. Also being short waisted the belt would be a cumberbund and the skirt floor length. If I had the body for it I would add a long necklace or drop earrings to add some interest.
    The second outfit is O.K. as the skirt would likely be to my knee and could be worn with tights but I find the blouse a little fussy with the jean type style of the pockets and it looks like it has pockets on the back. I think it would be better with a plaid shirt or cozy sweater.

  8. The only thing I like about this outfit is the colour of the top. It would be very flattering with my complexion. I don’t like the style, however, especially the wide sleeves which I think I’d find bothersome. I don’t care for pleated skirts and the fabric in this one looks too stiff and shiny for my liking. I also don’t care for the length.

  9. I don’t wear orange tones so first of all, the color of the top would not work for me. I have a short neck so I prefer necklines that are a little lower than the one shown. I used to wear pleated skirts but these days I prefer a pencil or a flared skirt. I avoid anything that would add bulk around the waist or tummy.

  10. I like the color of the tops (that shade of orange would be good for my coloring) and the neckline but don’t care for the sleeves (the drop shoulder, the wide bottom) No to both skirts (one is too long, the other too short – do I sound like Goldilocks?) and I’m not a fan of faux leather. But, I think the outfit on the left would be cute for a holiday party, not too dressy, not too casual…not sure I have many, if any, of those in the 2020 schedule.

  11. A half a century ago I would have worn the outfit on the right without hesitation (often wore mini skirts, love suede plus small prints) however as I am now vintage-matured (☺) I’m afraid I have to pass . As to the outfit on the left; I do like the color of the top but not necessarily its style nor does the skirt necessarily appeal to me BUT if that is a tuxedo leather or pleather belt (and not the skirt waistband) that would interest me.

  12. I’m not sure I “get” the orange outfit. I like the color/style of the sweater. The skirt is different. I’m not sure I would put the two pieces together. The sweater seems too casual for the skirt? I would dress up the skirt with a fitted black cashmere sweater and flashy jewelry. I will say this is a sophisticated way to do Halloween without looking like a kindergarten teacher.

  13. I like the first look even though the orange would not work for me and I probably wouldn’t wear real or fake leather. Still I am thinking how I can recreate this look next week with items in my closet. I would wear the second look if the top were a different color, assuming the skirt would be longer on me which is usually the case. This could be dressed down with tights and boots or athletic shoes, or up with sheerer stockings and low heels for work.

  14. I am misquoting,I think, But from the movie Bambi-“If you can’t say anything nice, don’t say anything at all” Applies here to those outfits!. Happy Halloween

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