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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I'm an NYC-Based Dad Who Is Always on the Move—This Is How I Redefined My Everyday WearEffortless, easy, and cool.
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Ignore the Haters—I Still Love These Versatile and Comfy Pants and Bet You Do TooSee how fashion people from NYC to Paris to London wear them for fall.
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My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic Rich-Looking Pieces for Fall 2025Everything is under $100.
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All of the Coolest People I Follow Just Bought Into This New Fall Denim ShapeNo, it's not barrel, wide leg, or bootcut.
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This Just In: The Denim Wash That's About to Dominate Every Cool Outfit This FallWill you love it or hate it?
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This Classic Shoe Is Every Parisian's Secret to Making Jeans Look Elevated in FallAnd you probably already own it.
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I Just Started Investing—31 Chic Pieces That Will Have Me Dressing the PartEffortless and elevated is the goal.
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Summer or Fall, This Is the Casual But Elegant Flat-Shoe Trend That Always Looks Good With JeansAs seen on Jennifer Aniston.
