As I’ve covered before, my 60-year-old mom, Nancy, is all about investing in staples to beef up the classic wardrobe she’s been honing for years. Her latest purchase? These timeless skinny jeans from Madewell. She gravitated toward this specific cut because, as she told me, "I liked the classic look and the fact that there was just enough stretch for comfort, but not too much.”
While she has a standard ensemble she tends to wear with her skinny jeans—basically a crew-neck T-shirt/knit and sneakers/ankle boots—she approached me with interest in uncovering a few fresh fits she could potentially try with her new skinny jeans this spring. Naturally, I sent her a range of forward looks from some of my favorite fashion people. What she loved about the outfits in question is that they were all seamlessly easy to put together and really could work for anyone at any age.
Interested in fresh skinny-jean 'fits as well? Keep scrolling to check out the chic outfits my mom wants to try (complete with her notes on why she’s into them). Plus, shop each look as well.
Skinny Jeans + Tucked-In Sweater + Draped Knit + Heeled Loafers
"Now this is a great everyday look. A timeless black sweater with skinny jeans is one of my go-tos, but I like how this one has the sweater slightly tucked in with another sweater on top for a cool layered look."
Skinny Jeans + Turtleneck + Trench Coat + Knee-High Boots
"I live in Wisconsin, so it's still cold outside. Therefore, I'm very into this outfit with the turtleneck (always sleek) and skinny jeans tucked into boots. I may actually try this one in the spring as well with a trench coat."
Skinny Jeans + Blazer + T-Shirt + Sweater + Booties
"I guess you really can't go wrong with skinny jeans, a T-shirt, and a blazer, right? Classic. I like how this look has the sweater tied off to the side as well. If I'm feeling a bit daring, I may try that too."
Skinny Jeans + Statement Jacket + Tee + White Boots
"I'm all about a statement jacket to make a jeans and tee outfit feel even more fashion-y."
Skinny Jeans + Blouse + Tank + Heels
"I tend to button my blouses all the way up, but I like how it's undone here to showcase a tee or tank. That paired with skinny jeans and my favorite little heels is great in my book."
Next, check out more 2020 trends my 60-year-old mother is eager to try.
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If You See Cool Girls in "Perfect" Jeans This Fall, They're Probably From This BrandYou're guaranteed to see them on Kendall Jenner and Hailey Bieber.
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The Chic 2-Piece Outfit Busy Fashion People Always Wear in SeptemberAwkward weather, conquered.
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See You Next Summer, Light-Wash Jeans—for Fall, This Is the Only Denim Trend That MattersAs seen on Hailey Bieber in L.A.
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You're 100% a Fashion Person If You're Styling Your Jeans in This Chic Way for Fall 2025A game-changing styling trick.
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Spotted on Kendall and Hailey: The Pant Color Trend People Are Swapping Blue Jeans ForIt girls with good taste know best.
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Cool It On the Skinny Jeans—Chic People Are Wearing These 6 Fall Denim Trends InsteadAre you taking notes?
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Jeans, Flats, Jackets, and Sweaters—The Best of the Best In Each Category For FallMeet your new hero pieces.
