The picture of me in 2017—wearing skinny jeans and boots—sparked lots of questions about how to wear the 2025 version: slim or straight-leg jeans with tall boots. The look is making a comeback, and I know many of us are thrilled. But we also need to recognize that the styling has evolved, which means our approach should, too.
See below for a replay of my Tipsy Tuesday Facebook live on this topic!
Fit Matters
- Choose skinny or slim-taper jeans, ideally high- or mid-rise, to enhance the waist and smooth the silhouette.
- Avoid light washes and distressing; instead, opt for dark, sleek denim.
- Ensure a clean tuck into tall boots for a seamless vertical line.
- Remember “high rise” is relative – find the best rise for your vertical body type (i.e., long waist, short waist, or proportional).
- Tuck them neatly into the boots to form a clean, uninterrupted line from waist to toe.
Here is a great example, from a favorite brand – Quince….high-quality designer-like jeans for $50. The Bella style on the left has a 10.5″ rise, and the Luna on the right has a 9.75″ rise. Both come in 26″, 28″, and 30″ inseams – intended to hit at the ankle bone.
Pay Attention to the Boot Style
- Stick with minimalist designs featuring a moderate 1–2 inch heel for subtle lift and comfort. Avoid bulky details or slouchy shafts that can shorten your silhouette.
- Suede is ideal—it molds to your leg and adds softness. Dark neutrals are versatile.
In the private Fall Style System group, I help members find the perfect boot for her unique frame, calf width, and budget—because when it comes to boots, there’s truly no one-size-fits-all.
Here are two examples (HERE and HERE) that are simple and sleek—great starting points.
I also have some budget options in my Amazon storefront linked here.
Create Balance with Your Top
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Pair slim jeans with boxy blazers, oversized button-downs, or chunky sweaters for contrast—but be sure your waist is still defined to avoid shortening your legs.
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Favor monochrome looks or open layers to elongate the body.
- Skip tunics that hit mid-thigh. Instead, try front-tucked knits or waist-length open jackets.
- Here’s a YouTube video by a petite influencer who does a good job of demonstrating this.
Try a Longer Jacket—Strategically
If you prefer more coverage over the hips or midsection, you can wear a longer jacket or blazer—just choose one with intention:
- Choose a structured jacket or blazer that tapers at the waist for shape.
- The ideal length hits just below the widest part of your hips—not mid-thigh—to elongate your legs.
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Pair it with a shorter or tucked-in top underneath to lengthen the leg line.
Stylist tip: Match/coordinate your jacket, denim, and boots for a continuous color column—especially enhancing for petite frames.
My 2017 photo reminded me just how much we loved our skinny jeans and tall boots—and it’s exciting to see the look making a comeback in 2025. But here’s the key takeaway…
While the core elements may be the same, the styling details are what make the updated version feel fresh, modern, and flattering—especially for those of us in midlife.
It’s not about chasing trends or tossing out what used to work.
It’s about knowing how to tweak and modernize those old favorites so we don’t get stuck in a time warp.
✅ Swap the tunic for a loosely front-tucked sweater or shape-defining jacket.
✅ Choose a boot with a sleeker shaft or slight heel for elongation.
✅ Try a longer jacket—with structure—if you want more coverage but still want to look pulled-together.
✅ Keep proportions intentional and the silhouette streamlined.
Small changes = major impact.
It’s a fresh way to revisit what we once loved—without getting stuck in the past.
Ready to Make the Shift Without Starting from Scratch?
If you’re thinking, “I still love my skinny jeans and boots—but I want them to feel modern,” you’re in the right place. The Fall Style System helps you:
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Make smart styling tweaks
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Shop only if needed
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Refresh your wardrobe using what you already own
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Receive done-for-you outfit prompts every evening—eliminating the daily “what to wear” stress and encouraging creative, fresh ways to wear your favorite pieces
No starting over. No chasing every trend. Just practical guidance to help you feel confident and stylish—effortlessly.
👉🏼 Join the Fall Style System now and I’ll walk you through it—step by step.
Scroll down for the replay of my Tipsy Tuesday Facebook Live on this topic!
