7 Skinny Jean Outfits That Won't Feel Dated in Fall 2019

Skinny jeans could easily be classified as one of the most timeless denim silhouettes out there at this point (despite their sometimes polarizing nature). That said, new denim cuts (baggy styles and the like) enter the scene season after season to give those classic skinnies a run for their money. But there are actually a few simple ways to keep your favorite skinny jeans feeling fresh. It really just comes down to pairing them with forward, of-the-moment pieces.
To help replenish our index of modern skinny jean outfits, we often turn to our favorite fashion girls for inspiration. In fact, after scrolling through the 'gram, it became evident that many of the style elite are wearing denim looks that feel particularly current and unique. Naturally, we rounded up the front-running ensembles for you here. Think of this as your guide for making skinny jeans impossibly cool right now and well into fall.
Style Tip: Experiment with an architectural statement top as an alternative to a standard button-down blouse. A pair of Mary Jane mules complete this A+ look.
Shop the look:
Style Tip: Add just the right amount of edge to your favorite black skinnies with a band tee and an oversize leather jacket. If it's slightly warmer outside, consider on-trend minimal sandals to soften the overall silhouette.
Shop the look:
Style Tip: Elevate distressed skinny jeans in your off-duty life with a pretty polka-dot blouse. While just about any shoe style would work here, a playful pair of feathered sandals brings the entire vibe to a forward dimension.
Shop the look:
Style Tip: The classic white tee and jeans look will feel so current with a cool outerwear pick like an oversize flannel jacket. If you really want to go for it, test out the matchy-matchy trend by coordinating booties in a similar hue.
Shop the look:
Style Tip: Whether you're looking for a polished denim look for travel or in your 9-to-5 life, this fit is for you. A blazer in a muted color (very right now) mixed with black skinnies and timeless loafers is a no-fail outfit formula.
Shop the look:
Style Tip: While a trench coat paired with skinny jeans may seem pretty simple, it's all about the shoe choice here. An electric pair of pumps offers up an unexpected twist to this now statement-making look.
Shop the look:
Style Tip: A white blouse that feels slightly offbeat (note the slouchy fit) tucked into sleek skinny jeans with loafers is actually quite modern if you're into that effortless, pared-down feel.
Shop the look:
Next, check out the skinny jean mistakes celebs over 40 never make.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
See You in the Fall, Skinny Jeans—This Trend Is So Much Better For Summer With Flats
Casual, chic, and comfortable all in one.
-
Lazy Luxury Is the New Quiet Luxury (Which Is Now Dead, BTW)
Here's how to do it right.
-
If a NYC Fashion Person Were Scrolling Through Amazon, They'd Buy These 27 Basics
Only the best of the best.
-
Of Course, 2025's Cali Summer Uniform Involves This Timeless Denim Trend
Can you take any guesses?
-
8 Pieces, 15 Outfits: Inside My Anti-Trend Summer Capsule Wardrobe
Outfit repeating like it's my job.
-
Red Who? Sorry, But Cool Fashion People Are Only Interested in Wearing Jeans With *This* Sneaker Color
It's the new red (and yellow, green, and silver).
-
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.
-
I Found It: The Only Denim Trend That Makes Flip-Flops Look Sophisticated Instead of Cheap
In Kendall Jenner we trust.