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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See You in the Fall, Skinny Jeans—This Trend Is So Much Better For Summer With FlatsCasual, chic, and comfortable all in one.
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Lazy Luxury Is the New Quiet Luxury (Which Is Now Dead, BTW)Here's how to do it right.
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If a NYC Fashion Person Were Scrolling Through Amazon, They'd Buy These 27 BasicsOnly the best of the best.
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Of Course, 2025's Cali Summer Uniform Involves This Timeless Denim TrendCan you take any guesses?
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8 Pieces, 15 Outfits: Inside My Anti-Trend Summer Capsule WardrobeOutfit repeating like it's my job.
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Red Who? Sorry, But Cool Fashion People Are Only Interested in Wearing Jeans With *This* Sneaker ColorIt's the new red (and yellow, green, and silver).
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Is It Just Me, or Is Everyone With Cool Style Suddenly Wearing This Specific Rich-Looking Outfit?It's taking over with a quiet kind of authority.
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I Found It: The Only Denim Trend That Makes Flip-Flops Look Sophisticated Instead of CheapIn Kendall Jenner we trust.
