Would You Wear It – Oversized Turtleneck

Would You Wear It – Oversized Turtleneck

Happy Saturday ladies, and welcome to your weekend!  This is the last weekend in October so I hope you have something enjoyable planned. It’s time for would you wear it so grab a cup of your favorite coffee or tea and let’s get to it.

Each week my friend Pam and I share a random mannequin we’ve photographed and ask if you would wear what it’s modeling. Stores are dressing these mannequins to showcase their newest merchandise and hopefully give us styling inspiration. Please look this mannequin over and tell us what you think.

You can comment on any or all of this. They’re both wearing an oversized turtleneck.

Would you wear one? How would you style it to fit your shape and lifestyle?

Here are the top 5 posts on A Well Styled Life in October


I’m joining some chic blogging friends to share our fall fashion.

Sharing my thoughts on accessories and a style point system for you to try when putting your outfits together.

Great fall finds from Talbots and my favorite new boots!

In a year full of problems, it’s important to pause and remember all you can feel grateful for. We got a surprising reminder.

Wearing head-to-toe fads can look tragic. But it’s smart to know the direction fashion is moving so you can keep an eye out for the trends that fit your style recipe. Here are things to try…

Here’s what’s most popular on AWSL this week:

aqua madewell polo sweater

Lots of you love the look of this polo sweater as much as I do.

This Calf Hair Leopard Crossbody is also very popular. It’s a great size and a fun way to add a pop of leopard to your outfit. The most popular item two weeks running is this cashmere crew neck sweater! fashion blogger jennifer connolly of a well styled life wearing ahlogen cashmere scarf and camel colored sweaterIt is time to start or finish our holiday shopping and this makes a terrific gift in any of the colors:)

Here are a few weekend sales:

J. Jill – an extra 30% off all sale styles

Ann Taylor: 40% off sweaters and tops, or 50% off 2+ sweaters and tops.

Banana Republic: Up to 60% off everything, and an additional 60% off clearance.

Chicos: 25% off full-price styles with code 56306

Loft: 40% off fall tops and sweaters with code TREATS.

J. Crew: 40% off fall layers with code LAYERUP.

Macy’s: 30% off select regular price items and 15% off beauty with code FRIEND.

Madewell: Take an extra 40% off sale with code GOODBUY.

Talbots: 40% off regular-priced styles and 50% off markdowns.

Now let’s go over and see what Pam’s mannequin is wearing on Over 50 Feeling 40

Thanks for reading and remember to wear what makes you feel fabulous and confident.


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


  1. Pam
    November 1, 2020 / 4:13 pm

    I love a regular size cowl neck sweater its my fav but super large cowls on a short necked girl is not an option. And I just don’t like a sweater over a sweater too muck bulk for short chubby women. But the winter white sweater is a classic.

  2. Helen Howes
    November 1, 2020 / 7:47 am

    Love the outfit on the left, love the oversized turtle sweaters, especially in winter white – goes with everything. Your tweed blazer is a winner. I have a similar one and usually wear it with a T-shirt, as I can never seem to find a white shirt that buttons perfectly ! I do like the dark V-neck you are wearing and I will try this for sure. Thanks for the tips.

  3. Audrey Sojonky
    October 31, 2020 / 4:30 pm

    Yes to both outfits. I think the large turtleneck collar provides a very flattering neckline to outset the face.

  4. Judy Bell
    October 31, 2020 / 2:46 pm

    I like these looks! I would definitely do the “front tuck” for myself. Gives the waist some definition.

  5. Cyndi Murdoch
    October 31, 2020 / 2:18 pm

    I love both looks and if I were tall and lean instead of under 5’ I would wear them in a snap. Both look very polished, and like someone said they look very business casual.

  6. Katelyn K
    October 31, 2020 / 1:10 pm

    Both of these ensembles are stunning representations of business casual and wardrobe staples.
    Although I live in eternal summer Florida, I would wear every piece if I lived in a colder climate. The oversized cowl neck sweaters would be great with leggings and booties and I especially like the embellishments on the sweater on the right. The oversized cowls have me dreaming of sitting fireside while sipping hot mulled wine or coffee.

    October 31, 2020 / 11:26 am

    I would wear the ivory oversized turtleneck and the tan skirt. It is so European in styling and so me!

    • Jennifer
      October 31, 2020 / 3:31 pm

      That would be pretty

  8. Marian
    October 31, 2020 / 11:23 am

    Oversized turtlenecks look really nice if I have enough hair to balance the look. I have a small head, a long neck and broad shoulders. When my hair is short, the oversize neckline overpowers my face. When my hair get to shoulder length, I can wear it well. Right now I’m in that awkward in between stage (not much haircutting these days), so I don’t know how it would look.

    It’s not my favorite for comfort. If it’s cold enough to wear a turtleneck sweater, I need the tight fitting one to warm my neck. I’d wear this oversized for looks more than comfort.

    BTW, I’ve enjoyed so many of your posts lately, especially from Canada. You’ve added a lot of great content and photos to your posts. However, now they load much slower on all my devices and it’s getting harder to leave a comment because I often get a forced “page refresh” and lose what I started to write.

  9. Cyndi
    October 31, 2020 / 10:41 am

    I like both outfits but would want long sleeves (outfit on right looks like shorter sleeves but might be pushed up above the elbow?) and closed toe shoes (rather than the open ones on the left). The soft white/ivory color would be more flattering for me than a white and the front tuck on the right looks modern and chic

  10. Pamela Over 50 Feeling 40
    October 31, 2020 / 10:29 am

    I like both looks and yes.,.would wear them!

  11. Nancy Walden
    October 31, 2020 / 10:11 am

    The coat/pant outfit is attractive but not something I’d wear. I prefer slim or straight-legged pants. I like cowl necks but oversized heavier fabrics would add bulk that would not flatter my body shape. I like the skirt and boot combo but I would not wear them with an over-sized sweater. I’d wear the skirt/book combo with a thinner knit that hit at the top of my hip.

  12. Cladette
    October 31, 2020 / 9:40 am

    I really like the outfit on the left. I could wear it in the area I live in for most of the winter. I do like the oversized neckline. I could not wear the outfit on the left.

  13. Patricia
    October 31, 2020 / 9:25 am

    I love both examples. I love oversized turtlenecks but, being 5’1”” and tiny, I couldn’t wear the cowl neck……too much material for one thing and getting the cowl neck to lay properly would be an issue. I like both the skirt and slacks. I love midi skirts worn with high boots only…..otherwise they would overwhelm my small build. These are 2 very classic looks that absolutely have a WOW factor and with a few changes to compensate for my small frame, I’d definitely wear them.

  14. Linda
    October 31, 2020 / 8:35 am

    I love the one on the left and wouldn’t change a thing! I have worn sweaters like these in the past too!

  15. Ann
    October 31, 2020 / 8:31 am

    Yes…I would wear both. I have a few similar sweaters and like that I can add a pin to the collar for some occasions!

  16. Dianne
    October 31, 2020 / 8:08 am

    Love both outfits so much!! Something I would definitely wear if the weather ever gets cooler her in Florida LOL Love all of the other outfits you are showing in this post. You look so sophisticated I all of them !! Happy Halloween 🎃🎃🎃👻👻👻

  17. MRSBEN2
    October 31, 2020 / 7:47 am

    What really caught my eye in this display is the coat as appreciate its pattern and neutral color however purchase would depend upon its fabric type, versatility and fit. (Weight/Purpose/Sleeves) As to the pants, prefer a straight or tapered leg but could see them working with many of the tops you featured in your Top Five October List which could make them an ideal wardrobe staple. Regarding the footwear; though do like the height of the kitten heels for myself would opt for something a little more stable. Also I’m not a fan of exaggerated pointed toes as in the boots whereas I do love open-strap shoes so weather conditions would dictate when I’d wear them otherwise my choice in a ‘shoe’ with either outfit, most likely would be a peep-toe with a substantial heel.
    Last but not least; do wear over sized turtle necks but would be more apt to wear the one on the left as shown whereas the short sleeved one as an overlay with a long sleeved top underneath and definitely not half-tucked. May belt either and would inquire if they came in other colors or even a winter white .

    • Jennifer
      October 31, 2020 / 8:28 am

      Thanks for sharing your styling ideas and why! Happy Saturday.

  18. Kackie
    October 31, 2020 / 7:35 am

    The turtleneck sweaters look soft, warm and comfy… But they would not be for me. The large turtlenecks would negatively emphasize my ample bosom! Not for me!

  19. Linda
    October 31, 2020 / 7:35 am

    Love both outfits. Best you’ve chosen yet. Sophisticated but not stuffy. Classic style. Lots of mix and match. Could wear either of these anywhere.

  20. Jackie
    October 31, 2020 / 7:13 am

    There’s way too much bulk in both turtles for my short self, I would look overwhelmed in either. Also way too warm for me these days.

  21. Lin
    October 31, 2020 / 7:03 am

    Love the look on the left. Right is not me.
    Would wear an oversized turtle neck. Very classy.
    Happy Halloween!

    • Jennifer
      October 31, 2020 / 8:26 am

      Happy Halloween

  22. Melissa
    October 31, 2020 / 7:00 am

    Echoing the previous comments. This is a WYWI that I would actually wear! These looks appeal to me. Neutral and sophisticated. I love turtlenecks for their warmth so not sure a sort sleeved one would get much wear.

    • Jennifer
      October 31, 2020 / 8:24 am

      Thanks Melissa, I hadn’t noticed the sleeves on the right.

  23. Joan
    October 31, 2020 / 6:28 am

    The one on the left has some appeal for me. I like the tunic length over dark pants but would choose leggings or jeans without the flair at the bottom. I wouldn’t choose tweed for the sweater/coat over it. But I’m assuming that the cowl neck is comfortable and stays in place exactly as shown. I’d skip the look on the right. Not a fan of the partial tuck look, but this sweater is way too bulky to pull off that look.

    I am still in love with your tweed blazer in those exact colors. If you ever find another one, please please provide a link. Also like the blue velvet jacket and would consider getting that one too. But my first love is that blazer.

    • Jennifer
      October 31, 2020 / 8:23 am

      I will keep an eye out for a blazer in those tones for you.

  24. Rose
    October 31, 2020 / 6:24 am

    Both outfits look very elegant. I’ve never quite got the hang of tucking in a thick sweater. Being short I would simplify and wear the sweaters with leggings. Nothing else would probably work for me.

    • Jennifer
      October 31, 2020 / 8:21 am

      I have a hard time tucking in chunky sweaters too.

  25. Susan McClelland
    October 31, 2020 / 6:13 am

    Both sweaters look cozy. I like the texture and length of the one on the mannequin on the right and would wear it as long as it has long sleeves (can’t tell from the photo). I like the bootleg pants and the skirt but wearing mostly jeans and leggings these days.

  26. Sue
    October 31, 2020 / 6:12 am

    Love the look of the outfit on the left. I agree with the comment about the sweater though—Short sleeves? Tucked in with all that fabric? I find oversized sweaters and cowls difficult to wear because they never seem to work well under coats for me…I end up looking like a sausage even though I’m tall and slim and the cowl doesn’t fit inside or outside of the collar. Wearing the coat open and with the more open neckline works here.

  27. Linda L
    October 31, 2020 / 6:12 am

    I like both of these looks but living in SoCal neither would get much play! I love the large cowl neck with the skirt; I used to own a very similar look when I worked & lived in ny. A short sleeve sweater with a cuddle duds cami underneath used to be a staple in my wardrobe.

  28. MP
    October 31, 2020 / 5:53 am

    Your pictures are not too clear, and I can’t see the sleeves. The sweater on the right looks to be sleeveless or short sleeves? Either way, what would be the purpose of that?
    I like the color and the details of the knit, but the cowls are too big for me. I would also like to know the fabric content — I like 100% cotton – not cheap acrylic.

  29. Jan
    October 31, 2020 / 5:47 am

    To me, both of these look just scream “gorgeous “!! I have always been a huge fan of the oversized turtleneck with the slouchy neck. It is such a versatile sweater, especially in this beautiful, neutral color. Today, I would pair it with pants or slim jeans but in the past, it would have been my choice to wear with a skirt. This is a classic look that I have always been drawn to and I guess it satisfies my need for comfort and confidence.
    Thanks for a fun post Jennifer.

    • Nancy
      October 31, 2020 / 6:11 am

      I love the oversized turtleneck because the regular one are always too tight on my neck. I like the look and would wear it with some slim jeans. The neutral color is perfect! This is a good one!!!!!!

    • Jennifer
      October 31, 2020 / 7:54 am

      Thanks Jan! I love them too

  30. Terri
    October 31, 2020 / 5:42 am

    I like both outfits. They are casual yet put together, the colors are neutral so can be mixed and matched with other clothing, and they look very comfortable.

  31. Diane B
    October 31, 2020 / 5:32 am

    These look so comfy and warm. The loose neck on this type is the only turtleneck that I wear, as the others make me feel like I am strangling. My fav. is the look on the left with the fuller leg pants and looser jacket. I would not tuck in the bulky sweater on the right and find it a strange look with that much fabric. These looks I would style with just larger earrings and bangles or rings as there is so much going on at the neckline already. Not sure why there are bare toes showing with a cold weather look. The sweater on the right would also look fantastic with skinny jeans and flat boots. Guess with temps at -8 C this morning I am thinking cosy sweaters.

  32. Cynthia B
    October 31, 2020 / 5:17 am

    Love love love oversized turtle necks in the winter. I really like both of the styles today, but wouldn’t feel comfortable wearing them. The one on the left, maybe…but to rock that on a 5’3 frame I’d have to wear high heals, which I’m liking to do less and less. The one on the right is gorgeous also, but the tucked in waist is problematic for me with a short waist….cuts me off in the wrong place.

    • Linda Simpson
      October 31, 2020 / 6:09 am

      Wow! Cynthia B, you nailed it on the head. I ditto your comments as a 5’3″ sized person.

  33. Penelope
    October 31, 2020 / 5:16 am

    Have worn these styles for years whether they were
    in-the-moment trends or not. I think they are classic and flattering.

  34. Doris Harding
    October 31, 2020 / 5:04 am

    Really love both of these looks and would totally purchase/wear either or both – as a matter of fact, both outfits remind me of outfits I had in years gone by! (Showing my age here!)

  35. Ann M
    October 31, 2020 / 5:02 am

    If I was going out, then yes, I would wear these loose turtlenecks. The outfits look sophisticated and stylish to me. That said, I’d never lounge around the house in any of these clothes. Perhaps crazy, but true… lots of extra fabric makes me feel cluttered to the point that I can’t get anything done.

    • Jennifer
      October 31, 2020 / 7:53 am

      That’s an interesting observation. Thanks Ann

  36. Susan
    October 31, 2020 / 4:33 am

    I bought a white oversized turtleneck last winter and practically wore it out!

  37. Jacki
    October 31, 2020 / 4:21 am

    Not for my petite 5’1″ self. Have never felt comfortable in a turtleneck of any type; this type has too much material and looks “fussy”. I prefer crew, boat, ballet or v-necks and will often add a scarf. I am getting itchy just looking at those photos!

    • Jennifer
      October 31, 2020 / 7:52 am

      Lol, I hate itchy sweaters 😉

  38. Paulette Levy
    October 31, 2020 / 3:37 am

    Both mannequins appeal to my sense of how to dress for my body type. First off, I wear oversized turtlenecks all winter, every winter. I love them with my leggings, skinny jeans and with our frosty winters they definitely work to jeep me warm.
    I love the look on the left. I will have to try with the wider leg pants as shown. I don’t own any right now. The skirt on right is just about the longest I would go. (Personally not a fan of midi skirt length). With the tall boots, this works in my opinion. The oversized turtlenecks are a win for me!

    • Valerie
      October 31, 2020 / 6:53 am

      I love the oversized turtle neck. I would wear it with leggings or my skinny jeans. The outfit on the left I would definately wear. I can not wear anything tucked in it cuts me in half.

    • Jennifer
      October 31, 2020 / 7:52 am

      Thanks for your thoughtful comment Paulette. Happy Saturday.

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