Skinny Jeans Are Back—Here's How to Style Them for Your Hourglass Shape in 2025

I'm a millennial and I'm not apologizing for it: skinny jeans are back for fall 2025 and I'm thriving. But here's the thing—wearing them now isn't the same as wearing them in 2015. We need to style them in a way that feels current and actually flatters our individual bodies.

That's exactly why we built LookSky. Think of it as your personal AI stylist with virtual try-on built in. We scan all the trending outfits from your favorite influencers and the freshest new arrivals, then filter everything to show you only what works for your specific body type, color season, and style. And because we know online shopping is basically a gamble, we added realistic virtual try-on so you can see how pieces actually look on you before you commit.

I'm breaking down three complete outfits built specifically for hourglass shapes. Not hourglass? Don't worry—we're doing an entire series on styling skinnies for every body type, from pear to apple to rectangle and beyond.

Q: What tops work best with skinny jeans for hourglass shapes?
Fitted or semi-fitted styles that define your waist—think wrap tops, belted pieces, or cropped lengths that hit at your natural waistline and balance your proportions.

Q: Should hourglass body types wear high-rise or mid-rise skinny jeans?
High-rise skinny jeans prevent waist gapping and sit securely at your natural waist, creating the most flattering silhouette for hourglass curves.

Q: How do you style skinny jeans to flatter an hourglass figure?
Focus on fitted tops, structured jackets that nip at the waist, and high-rise jeans—the goal is to emphasize your defined waist while balancing your curves top to bottom.

Download LookSky's now and take our style quiz to see exactly which outfits we recommend for your body shape.

• Why it works: The ultra-high rise sits at your natural waist (preventing gapping) while the vintage stretch fabric holds its shape through curves. The slim leg balances your hips and creates that coveted hourglass line from waist to ankle.

• Why it works: The cropped length hits right at your natural waist, emphasizing your most flattering feature without adding bulk. The V-neckline draws the eye vertically and balances your proportions, while the fitted silhouette follows your curves. Cashmere adds polish without sacrificing comfort—this is elevated casual that works for the office.

• Why it works: The single-button closure hits right at your waist, creating instant definition without bulk. The structured shoulders balance your hips, and the slightly longer length elongates your torso while still showcasing your shape. This is the blazer that actually fits hourglass bodies.

Expert Tip: Ballet flats can look a little dated with skinnies. Try Mary Janes instead.

Want to see this outfit styled on your exact proportions? Try it on virtually in LookSky—no dressing room, no guessing, just outfits that actually work for your hourglass shape.

• Why it works: The high-rise waist sits securely at your natural waist (no gapping), while the straight leg creates a sleek line that balances your hips. The black wash adds instant polish and elongates your legs, making this the perfect date-night denim that actually fits your curves.

• Why it works: The square neckline balances your proportions and draws attention to your décolletage, while the long sleeves add sophistication. The fitted silhouette follows your curves without clinging, and the slightly cropped length emphasizes your natural waist—the most flattering point on an hourglass frame.

• Why it works: The cropped length hits right at your waist, creating perfect hourglass proportions without hiding your shape. The structured shoulders balance your curves, the asymmetric zip adds edge, and the luxe suede elevates the entire look. This is the moto jacket that finally understands how to flatter an hourglass body.

Expert tip: Pair this with pointy slingback kitten heels or pumps.

See how this look translates to your frame in LookSky's virtual try-on—because hourglass styling isn't one-size-fits-all, and you deserve to know what works before you commit.

• Why it works: The ultra-high rise prevents waist gapping and sits securely at your natural waist, while the stretch fabric moves with your curves. The stacked hem adds visual interest and a fashion-forward edge, and the slim leg creates a sleek line that balances your hips. This is the jean that finally fits hourglass bodies right.

• Why it works: The oversized rugby silhouette balances your proportions when styled cropped or half-tucked, while the horizontal stripes draw the eye across your shoulders and bust. The collared neckline adds structure, and the relaxed fit creates that effortless cool-girl vibe without drowning your waist—especially when paired with high-rise bottoms.

• Why it works: The belted waist is everything for hourglass shapes—it creates instant definition at your narrowest point. The structured shoulders balance your curves, the midi length adds drama and sophistication, and the classic trench silhouette elevates the entire look from casual to polished. This is the coat that celebrates your shape instead of hiding it.

Expert tip: Pair this with burgundy penny loafers.

Ready to get inspired by the creators in our Discover feed? Each day we'll pull today's viral OOTDs that are matched to your lifestyle, vibe, shape, and more.

Q: Why do skinny jeans gap at the waist on hourglass figures?
Standard sizing doesn't account for the hip-to-waist ratio common in hourglass bodies. Look for high-rise styles with contoured waistbands or curvy-fit denim that's cut specifically for defined waists and fuller hips.

Q: Should hourglass shapes tuck or untuck tops with skinny jeans?
Tuck or half-tuck to define your waist—it's your most flattering feature. Leaving tops untucked hides your natural shape and can create a boxy silhouette that works against your proportions.

Q: What jacket length is best for hourglass body types with skinny jeans?
Cropped or waist-length jackets that hit at your natural waist create the most flattering proportion. Longer jackets should have a defined waist (like a belted trench) to maintain your hourglass shape.

Q: Can I try these outfits before buying?
Yes—LookSky's virtual try-on lets you see how these exact pieces look on your body type, color season, and proportions before you commit. No guessing, just outfits built for your hourglass shape.

Q: What's the difference between styling apps and LookSky?
Styling apps guess based on trends. LookSky shows you what actually works—for your shape, your measurements, your life. It's virtual try-on meets personal shopping, without the personal shopper price tag.