A Chic Way to Wear Skinny Jeans Over 40 in Fall

Are you a fan of skinny jeans?  They’re not just for casual looks! Let’s explore the chic and sophisticated side of skinny jeans this fall by pairing them with an oversized sweater.


Creating a classy, slimming, sophisticated look with skinny jeans starts with the perfect jeans. These Paige jeans have a high waist and a stretchy fit, making them comfortable and stylish.


Black is always chic and slim, especially when paired with skinny jeans and black suede booties. Your legs will look like they go on for miles.

For a chic look, an oversized sweater is a must. But here’s the key: balance. If you’re opting for skinny jeans, go for a wide and oversized sweater on top. This elegant green rib knit sweater with a deep V-neckline is perfect.



Cool sunglasses help, too. The pair I’m sharing are the  Ray-Ban Hexagonal Flat Lenses. This style is a cross between a circle and a square and has a refined look and feel.

The lenses are called Silver Flash. They’re a hybrid surface of lenses that provides super high shine, but the mirror coating helps reduce glare big-time!

A great bag, like this Michael Kors one with lots of gold hardware and texture, adds fabulous glam to this look.


Be sure to tuck the sweater in at the front. Try a half-tuck so the sweater gently drapes over and hangs at the back.


Finish with a beautiful layered chain necklace, and you have a great way to wear skinny jeans that is chic at any age!

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16 thoughts on “A Chic Way to Wear Skinny Jeans Over 40 in Fall

  1. Tops with skinny jeans: must cover tush. My rule for a classy look: is solid neutral colors and layers. Prints: absolutely no cheap-looking synthetic print tops. A cheap top looks like a cheap top, and sometimes expensive print tops look cheap, too, if the fabric isn’t quality and doesn’t drape well. SCALE is significant to me in putting a layered top over skinny jeans. Ex: just the right amount of white should show. Scale is significant with prints, too. I.e., the size of the person matters. I have to say that I am just much more comfortable in subtle, simple clothes, and comfort is essential.
    I would add that I am over 60, and these are my rules. This blog is excellent; I love the interactive aspect. I would occasionally add photos –but so far, I don’t see that option.

  2. I agree about models that all should be 40+. That’s why More magazine went out of business… it wasn’t real; they abandoned their loyal audience, then couldn’t compete with younger mags…
    Also, while I enjoy your site, it would be nice to include clothes for gals 60+, flabby arms, necks, hanging jaws, pooched tummies, varicosities in legs, Wider hips, etc. the old grey mares aren’t what they used to be. If you know your stuff, make it work for women over 40! And yes, weight often increases, and breasts enlarge!

    So 40/50’s attractive, more youthful looks are terrific. But how about beautiful eyes for women who know who they are, are older, more limited, and a bit more challenged in the fashion world, yet still want to be classy?
    Again, on appropriate models… ;0-)

    1. Hi Deb, Thanks for your insightful comments.

      The topic of 40+ models comes up often, and the reality is my hands are tied. I show clothing from all the major brands, and none of these brands hire 40+ models, or if they do, they sure don’t look it. I often cut the heads off the models in these photos and show the clothes. It’s not perfect, but it helps a bit.

      I also try to supplement by showing 40+ bloggers and Instagrammers in outfits they own in my Styleblazer series. I’m also starting to model more clothes.
      I’m trying to let brands know what my readers want, but they are still chasing the young demographic. It’s frustrating for us all.

      As for the 60+ requests, they’re growing. I would love to get some feedback from other readers on this too. What are everyone’s biggest dressing challenges at 60+? What is different about how you want to dress at 50 compared to 60?
      Would you like to see a special 60+ section on the blog?
      Please leave your comments below.

      Thanks again, Deb, and if you have more suggestions, feel free to write. I always welcome feedback from everyone! Cheers! Deborah

  3. I never stopped wearing pants with a flare or wider leg…skinny jeans don’t look good on my pear shape. Closest I’ve gotten is a regular, straight leg of jeans. My dressy trousers are always with a slightly wider portion. Polka dot pants would make my big thighs look bigger! However, I have been wearing straight legs with the hems rolled up about ankle-or-shorter-length, which is a good look for me. One must know what looks good on one’s body, no matter what is “trendy.”

  4. I love these looks, but I keep seeing that jeans and pants look too short. As a tall person, I have bad memories of these being called ‘high-waters.’ Is that fashionable now? Or those cropped pants? Please explain.

  5. Hmmm. I do love the look – but unfortunately, not on me! I feel like they accentuate my hips. I have worn them this winter with chunky boots, which helps, but I think I will be staying with my bootcut jeans and maybe capris with a little flare at the bottom for the spring and summer.

  6. I purchased a pair of pin dot jeans that were boot cut and a bit boring. I altered them to make them skinny and have gotten tons of compliments.

  7. I love the skinny look, but the dots would not be for me on the pants or the top. I’m tiny in stature, and beads always make me look/feel like Minnie Mouse, though I love the mouse! I prefer solid colors, so I am not overwhelmed with too many patterns. I LOVE the perforated tan boots with look #3. The chunky heel is perfect for me. I went to the website to check them out, and the price is reasonable.

  8. I love tunics; they hide many sins, e.g., my arms, waist, and butt; however, I don’t have the figure for skinny jeans, leggings, jeggings, etc., because I have big legs though I am a size 12.
    Are straight-leg jeans my best bet with tunics?

    Thanks, Deborah; this way, over 40 gal always looks to your website for inspiration.

  9. I’d be interested in reading a post on when you shouldn’t wear skinny or how women who aren’t toothpick thin can wear them and look good. I’m a size 10 (and 5’6″) and feel ridiculous in skinny jeans, even when paired with a long blouse.

    1. I feel like this too. I have found I can wear them in the place of leggings and wear boots! They are great tucked-in boots with no extra fabric to fold over! Then the fancy stitching on the shoes shows as an extra.

  10. It would have been helpful to show how women over 40 could wear skinny jeans and look ok in them! Instead of photos of 20-year-olds with perfect bodies.

  11. Fantastic outfits! I’m so in LOVE with those polka dot skinny jeans!!! Thank you for all the inspiration!!!

    1. Skinny jeans, the late 80s, early 90s throwback/throw-up do not look good on 6’2″ supermodels & they sure don’t look good on your average 40+-year-old. Stacey of “What Not To Wear” fame said high-waisted, tight-to-the-ankle pants make a woman look like an ice cream cone & she is SO right. Low-waisted flared & boot cuts are even worse. Let’s show off those fat rolls, ladies; they are SO sexy!

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