Would You Wear It- Casual and Warm

Happy Saturday ladies and welcome to your weekend. I feel like I’ve eaten my body weight in turkey over the last 48 hours and still have tons of leftovers! I’m searching for a great recipe for Turkey Pot Pie so if you have one, please send it my way:)

It’s time for would you wear it, so grab a cup of your favorite beverage, and let’s have some fun.

Each week, my friend Pam and I share a random mannequin we have photographed and ask if you would wear what it’s modeling. Please keep your comments personal to your style.

Would you wear this outfit? Please share how you would style it to work for your shape and lifestyle. It’s fun to get inspired by your styling ideas!

I also spotted this camera bag-shaped crossbody that adds a fun touch to a casual outfit. I have a vintage Kate Spade in this square shape and know it holds a ton of stuff!

Here’s what’s popular with AWSL readers this week-

This Back Massager, which tells me I am not the only one with a stiff neck:)

jennifer connolly wearing 1901 star swatwe and blue jeans


Black Friday has turned into Cyber Week with massive sales and huge discounts which, to be honest, is often nauseating. In fact, one of my favorite skincare lines was closed yesterday to cut down on hyper-consumerism!

I can’t tell you how much I appreciate you shopping through my links, but I don’t want to overwhelm you so I’m just going to share a few of my favorite picks in my posts. You can see yesterday’s picks here.


40% off your purchase with code 79855 and an extra 60% off already reduced with code 26975.

J.Crew Factory

60-70% off everything plus an extra 10% with the code HOLIDAY!  60% off clearance with the code GIFTY.

  • This Vail Parka comes in Heather Dusk plus the most gorgeous shade of Eggshell Blue. It’s a classic bestseller that comes in regular and petite.
  • I love, love these flat Calf Hair Leopard Booties. They add zip to jeans and a simple sweater.
  • This Chanel looking cap-toe pump dresses up any outfit and looks especially good because they shorten the look of your foot.

Alo Yoga

up to 70% off sale and 20% off new while supplies last. You can give the gift of health to yourself or a loved one on your list.

  • The Alo Moves Annual Membership  What’s in this box: annual membership to Alo Moves brings at-home fitness, yoga, and meditation, not to mention the wellness, joy, and peace that come along with mindful movement. Alo Moves brings members the world’s best instructors, teaching epic video classes that turn anyone’s home into a home gym, yoga, and meditation studio! And you seriously can’t beat the value of 12-months of Alo Moves membership for $99.
  • The Ultimate Gift Of Wellness contains everything you need for you or your loved one’s practice. Are you reading this Santa??
  • Their super popular Warrior Yoga mat is on sale in tons of colors.

Ulta Beauty

up to 50% off your favorite products and devices. You can buy online and either pick up in-store, pickup curbside, or have things shipped.

  • This Super Sonic Deplaning Tool is on sale and to be perfectly honest, it did not live up to its promises for me. I have and love a lot of at-home beauty tools but this isn’t one of them. It was just a dud for me so I went ahead and bought these Schick Facial Razers which do an amazing job at a fraction of the cost! I’ll do a video for you on how I shave my face soon. I actually buy the giant pack at Amazon which saves even more money. Some things are well worth their price and others are not so I’m here to help to spend your money wisely.


Now let’s go over to Over 50 Feeling 40 and see what Pam’s mannequin is modeling!

This post may contain affiliate links which won’t change your price but will share some commission.


  1. Pam B
    November 30, 2020 / 1:08 am

    I would wear all of it together. And you could wear the shirt with another outfit also. I liked everything you showed today. It’s my first time giving opinion about the clothes I don’t like to say I anything negative about an outfit.

  2. Pamela Over 50 Feeling 40
    November 28, 2020 / 1:43 pm

    Sorry to be so late today! I would wear the coat…and both tops, but not tucked in. The jeans are a no go…I don’t care for the style or distressed look. I personally prefer a more tailored jean.

  3. Eve
    November 28, 2020 / 1:09 pm

    I like both but do prefer a V neck and longer pants. The color could be lighter too. Love crossover bags. I usually leave home with just my phone, credit card and glasses. Since my hair is short and I wear very little makeup, they work for me. I bought camera bags years ago to haul around my stuff.

  4. beth byrd
    November 28, 2020 / 11:46 am

    I like the casual vibe with both outfits. I think a black blouse with jeans is a classic look that can be worn by a woman of any age!

    I do the ‘tuck’ with my tops, but tailor it depending on the waist and look of the outfit. I think it is a fun look.

  5. Becky
    November 28, 2020 / 11:41 am

    The coat is a no. If past experience is any indication, the curly white trim would be matted & dirty looking after it is worn a few times in a Midwest winter. I would wear both tops. The patterns are interesting & not over powering, & both have classic styling. I wouldn’t wear the jeans. I prefer at darker wash & do not like frayed hems at all.

  6. Cyndi
    November 28, 2020 / 11:04 am

    The outfit is cute and I’d wear a version of it. Love the print on the blouse and while the neckline looked high on the mannequin, when I clicked on the link it looks fine. I’m a cooler natured person who lives in an area with true winter weather, so not sure those short sleeves would get much wear. On the fence about those particular jeans: the length and the frayed hem. I’m slowly adjusting to the lighter wash but think it pairs very well with black.

  7. Gerri
    November 28, 2020 / 9:16 am

    I would wear this outfit, with the long sleeve polka dot blouse. The only thing I would change would be the jeans. I abhor high water pants! I would go with a longer pant, probably boot cut.
    Coat looks very comfy.

  8. Caroline Lane
    November 28, 2020 / 9:14 am

    Hello, I’ve only recently found your site and am thoroughly enjoying the blogs. I was initially drawn to the site by the lovely photo of you wearing the navy edged ivory(?) jacket, so natural looking!….. and I love your navy star sweater.
    I like the metallic jacquard top in the first photograph.
    I’m from the UK and am very jealous of your Talbots clothes. I’m not sure if it was the same company, but there used to be a Talbots concession in one of our department stores, but I haven’t found one over here recently. Shipping is quite expensive for us from the USA, especially if the pieces don’t fit when they arrive!
    On my trips to the States, I have always ‘stocked up’ at Talbots, JCrew and Chico’s, but my favourites have always been White House Black Market and Tommy Bahamas.

    • Jennifer
      November 28, 2020 / 4:29 pm

      Welcome, Caroline, I’m so glad you’ve joined us!! Shipping and duty charges are really crazy, I know.

  9. Connie
    November 28, 2020 / 8:38 am

    I like both outfits, but I wouldn’t wear unfinished hem jeans. The calves hair purse is darling. The Nordstrom “Dallas Cowboys” sweater you showed again, made me buy another one…This time for myself! My sister lives in Dallas and I’m in CA, so I won’t run into her wearing it 🙂

  10. Joanna
    November 28, 2020 / 8:29 am

    I’ve been deleting many of the blogs I follow because it’s nothing but lists of all the sales. Too much! Thank you for only pointing out a few and still including your Would You Wear It.

    It seems a lot of women are shaving their faces. How often do you need to shave, does it grow back in coarser or darker… Look forward to your video.

  11. Jane
    November 28, 2020 / 8:14 am

    It’s a yes from me. On snow days I would add a knee high boot, slushy days a rain boot.

  12. Diane
    November 28, 2020 / 7:56 am

    I love both outfits and would wear them. I wear most any color or style as long as I feel comfortable in it.

  13. Elaine @ Following Augustine
    November 28, 2020 / 7:07 am

    I love the casual, comfortable look of today’s outfits. I would choose the blouses in a lighter colour though as black near my face doesn’t work well with my pale complexion. I’d wear the jeans as long as they’re not cropped as the shorter length isn’t suitable for our cold, snowy Canadian winter, but I would prefer a pair that aren’t frayed at the hem. Though the coat would look better on my if it was navy or grey instead of black, I would definitely wear it. I love the necklace!

    • Jennifer
      November 28, 2020 / 8:02 am

      Thanks Elaine. I know the necklace is at Madewell.

  14. Jackie
    November 28, 2020 / 7:02 am

    I agree with some of the other ladies, no black near my face anymore, no frayed or cropped jeans for me. I like the crossbody purse, but would need an organizer inside.

  15. Rose
    November 28, 2020 / 6:58 am

    Yes I love both outfits! Haven’t worn bootcut jeans in a while but am ready to try

  16. Lisa
    November 28, 2020 / 6:31 am

    Love the look for both outfits, but not crazy about some of the details. The sleeves for the metallic print wouldn’t work for me, and the length of the bootcut pants is a no go. The pajama blouse is a nice find and would be a good wardrobe addition.

    • Jennifer
      November 28, 2020 / 8:00 am

      I love that pajama blouse too. What an odd name it has.

  17. Sharon
    November 28, 2020 / 6:25 am

    YES to both outfits! I’m very small and both outfits would work for me and not overwhelm my frame! I think they are styled beautifully.. love your stars sweater too..

    • Jennifer
      November 28, 2020 / 7:55 am

      Thanks for the recipe!!

  18. Marcia
    November 28, 2020 / 6:06 am

    Yes to both outfits. Colours are great, as is the casual styling. I would wear all pieces.

  19. Susan McClelland
    November 28, 2020 / 5:56 am

    I like both outfits. The crop length jeans and the short sleeve blouse are not super practical for winter in Ontario, but I would wear them in the spring and fall. Same with the coat. Casual is my mantra these days

  20. MRSBEN2
    November 28, 2020 / 5:53 am

    Re the metallic print blouse; not that I dislike it but am not fond of crew neck styles (would prefer the v-neck one to the right of it or the polka dot one shown). Also I personally like a longer sleeve length. As to the 3/4 (parka) length jacket regardless I consider it casual it would depend upon its quality of fabric (many overtime pill) and faux fur detachable collar plus its zipper but even then I might pass because of its large patch pockets and I would also consider its weight. In respect to the ocelot pattern CB-camera bag; since its a tad larger from what I am toting these days and shall also add I feel that the piece of leather securing the strap could be a better match; it too is a ‘no’. (FTR it runs at $225.00 CA and feel I could find something similar but more to my liking/need.) Last but not least; a ‘yes’ to the jeans.
    P.S: Re the pull-thru faux fur scarf; purchased similar last year to wear with my (casual) puffer coat however bought two and constructed removable cuffs out of one to dress it up a wee bit. Also do love the Chico’s double collar/wool blend coat and would snap it up if I was sure of my size as consider both its camel color and style ‘classic’.

    • Jennifer
      November 28, 2020 / 7:54 am

      You are so cleaver to make cuffs from the second scarf!!

  21. Jan
    November 28, 2020 / 5:46 am

    First impression, I love both of these looks! I would definitely like to try on the coat. Our winters can be brutal and this coat with it’s length and full zipper would help block out those chilly winds. I prefer the 2nd top with the muted polka dots but would wear it untucked.
    The basic, simple lines of these outfits appeal to my typical choice for comfort and confidence.
    I do like the cross body bags also. They seem to elevate the look to a bit more youthful?

    • Jennifer
      November 28, 2020 / 7:52 am

      I love your explanation. Comfort and confidence…hard to go wrong with that.

  22. - Vicki Mikola Dack
    November 28, 2020 / 5:41 am

    Fabrics are too light for CO weather! Need Warmth…Not flimsy material garments. Recently moved from AZ (mid-way between PHX & FLG) and need heavier[thicker] style gloves, jackets, socks, sweaters, and tunics to keep from freezing. At least for the first winter here. Hopefully by the 2d year of winter months — blood has thicken up a bit. And make sure to use sunblock lotion [daily] due to higher elevation!

    • Christie Newman
      November 28, 2020 / 6:46 am

      Love the look of the muted polka-dot shirt and the coat is perfect for California, but I would pair it with skinny jeans with a pair of high boots .

    • Jennifer
      November 28, 2020 / 7:51 am

      That’s a fun move!! How exciting

  23. Tina
    November 28, 2020 / 5:34 am

    Yes! I would wear both outfits. Bootcut is my favorite jean. I would prefer a lighter gray or navy for blouse color but can find a way to add color by my face.

  24. Lori Stewart
    November 28, 2020 / 5:33 am

    I love the outfit. I haven’t tried the partial tuck, but would give it a go to see how it looks (probably not good with my muffin-top). Although I do like the purse, I might try a bright color, I have a red cross-body purse that might add that pop of color, or add some color with my footwear. The Anorak looks nice and cozy and I like that it is longer. On cold days, bomber jackets only keep your top half warm, the longer jacket provides warmth to almost your whole body.

    • Jennifer
      November 28, 2020 / 7:50 am

      I agree about longer coats. If my bum is warm, I’m warm.

  25. Melissa
    November 28, 2020 / 5:32 am

    I like both of these outfits. Loved that first blouse until I saw the sleeves. And I love your star sweater!

  26. Linda L
    November 28, 2020 / 5:31 am

    I like both looks but they wouldn’t make the cut in this climate. I gave all my wool coats away when I moved to SoCal; there is really no need for them. Love the camera bag!

    • Jennifer
      November 28, 2020 / 7:49 am

      I don’t need too many coats either but I love them!!

  27. Paulette Levy
    November 28, 2020 / 5:17 am

    Yes yes! I would wear both outfits- they’re part if my usual casual going out style nearly all of the time. I sometimes mix it up by just adding that classic white shirt with silk scarf knitted at neck…vibrant colors!
    And I love that boxy cross body bag too….nice and good to know it holds a bit more! Tres chic.

  28. MP
    November 28, 2020 / 5:15 am

    I like the coat. I don’t like the large pockets in the front — I prefer seam pockets. The large pockets can stretch out and look awful. I like the print of the metallic blouse – not the sleeves. The fabric would make a nice v-neck tshirt. Frayed hem jeans no. I am a polka dot fan but the dots on the blouse are too big for me. Subtle is my game. Happy Saturday!

  29. Deb
    November 28, 2020 / 5:10 am

    I would wear both outfits. Home run this week!

  30. Leslie B
    November 28, 2020 / 5:07 am

    I love everything today and would wear everything. The only thing I would do is wear both tops outside of the jeans. I love the half tuck on other people but every time I try it I look too bulky and am afraid people will think I’m trying to look too young.

  31. Michele
    November 28, 2020 / 4:58 am

    These would both be a yes as long as the jeans were full length. I’m usually not a fan of polka dots, but the pattern on the button-up blouse is so subtle. It actually gives the blouse a touch of added interest. I prefer the style of the crew neck over the button up…just a personal preference. I love a crossbody bag and the camera style is a favorite of mine. You are correct about them being able to hold a lot of stuff. The patterned one shown adds a perfect pop of color.

    • Jennifer
      November 28, 2020 / 7:48 am

      Thanks For explaining the details. I love how much those bags hold yet they’re compact!

  32. Linda
    November 28, 2020 / 4:34 am

    I like both outfits! I would prefer longer jeans though. Love both purses too!

    • Jennifer
      November 28, 2020 / 7:46 am

      I hear you! Being short, these may be long enough for me. Most models are 5’9 or more

  33. Linda V
    November 28, 2020 / 4:33 am

    I love the necklace in the first picture. where would I get that????? also love the polka dot blouse

    • Jennifer
      November 28, 2020 / 7:45 am

      It’s at Madewell.

  34. Linda R Gaertner
    November 28, 2020 / 4:31 am

    I would wear both outfits and I love the leopard print crossbody bag.

  35. Nancy
    November 28, 2020 / 4:22 am

    Ditto to the above comments. I would wear both outfits but not in black. Not flattering near the face. Particularly as I age, I find that black near my face washes me out and makes me look tired.

  36. Candace McElroy
    November 28, 2020 / 4:17 am

    Yep to both. Luv the casual but yet classy looks.

  37. Lorraine
    November 28, 2020 / 4:10 am

    I love these outfits. Casual just like ME! I would add a pop of color with a great scarf or wool beanie for those cool winter days!

    • Jennifer
      November 28, 2020 / 7:41 am

      Beanies are so fun!! I have to dig mine out.

  38. Shelley
    November 28, 2020 / 3:56 am

    Yes, I would definitely wear both outfits, although I would want the blouses in different colors because black near my face makes me look sallow.

  39. Lori H
    November 28, 2020 / 3:34 am

    I love both outfits! Simple and classic.

  40. Cindy
    November 28, 2020 / 3:10 am

    These outfits are ok, I’d just prefer the blouses in a lighter color. I tend not to wear back right next to my face. I like the jeans. And the crossbody bag i sa definite yes!

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