The Best Shoes to Wear With Every Pant Style in 2025

What Shoes to Wear with What Pants in 2025

Straight-Leg Pants

Straight-leg pants are a classic that just won’t quit—and thank goodness. They’re versatile, flattering, and easy to wear. Whether you’re styling jeans, trousers, or casual cotton pants, the right shoe can polish the whole look.

Best shoes to wear with straight-leg pants:

• Loafers: They give just the right touch of polish for a smart-casual outfit.
• Ballet flats: A favorite comeback in 2025, they’re comfortable and pair beautifully with straight jeans or trousers.
• Sneakers: Clean, minimal sneakers give a laid-back look that’s great for everyday.
• Ankle boots: Choose a slim-fitting boot that fits close to the ankle and tuck the pants over or let them skim the top.

Avoid: Chunky platforms or shoes with too much volume—they can make your feet look heavy compared to the clean line of the pant.

Wide-Leg Pants

Wide-leg pants are everywhere right now—from linen beachy pairs to elegant high-waisted trousers. But they can be tricky when it comes to shoes, especially if you’re not super tall.

Best shoes to wear with wide-leg pants:

• Platform sandals or wedges: These add height without sacrificing comfort.
• Pointed-toe heels: Great for elongating the leg, especially under full-length wide-leg pants.
• Chunky sneakers: A great option for a cool, modern, off-duty look.
• Mules: Sleek mules with a bit of a heel look effortlessly stylish.

The key here is balance. Because the pants are wide, a little height from your shoes goes a long way.

Cropped Pants

Cropped pants show off your ankles and your shoes, so you’ll want to make sure you’re stepping out in style.

Best shoes to wear with cropped pants:

• Low-profile sneakers: Think white leather or canvas options that are neat and tidy.
• Loafers or slides: Chic and comfortable, these look great with cropped straight or flare styles.
• Block-heel sandals: A stylish and supportive option when you want a little lift.
• Ankle boots (with a low shaft): Choose boots that stop just below the hem so your pants don’t bunch.

Watch out for: Shoes that come up too high on the ankle or cut off the leg line—they can make you look shorter than you are.

Flare Pants

The 70s called, and they’re still loving flares! This retro style is back in a big way for 2025, from denim to knit pants.

Best shoes to wear with flare pants:

• Heeled boots or booties: Classic under denim flares and perfect for fall and winter.
• Pointed-toe heels: These add instant polish and lengthen your legs.
• Platform heels: Yes, they’re back! And they’re great under dramatic bell-bottoms.
• Sneakers (with a thick sole): Casual, comfortable, and works with more relaxed flares.

Important: You want your pants to nearly skim the ground (without dragging), so your shoe height matters more here than with other styles.

Barrel-Leg or Balloon Pants

This is a newer silhouette that’s becoming more popular—think pants that are roomy through the thigh and taper at the ankle.

Best shoes to wear:

• Slim-fitting ankle boots: These work well because they fit snug at the ankle and don’t compete with the volume of the pants.
• Sleek sneakers: Not too chunky, not too dainty—find a happy medium.
• Flat sandals: Especially if the pants hit above the ankle, a strappy sandal looks feminine and fresh.

Avoid: Bulky shoes that add more volume to an already voluminous silhouette.

Cargo Pants

Utilitarian and laid-back, cargo pants have come a long way. Now they come in satin, twill, even denim—and women over 50 are rocking them.

Best shoes to wear with cargo pants:

• Fashion sneakers: These keep the vibe casual and on-trend.
• Combat boots: Lean into the utilitarian style with a lightweight pair for spring or fall.
• Slides or sport sandals: Perfect for warmer weather and travel days.
• Low heels: Add just a touch of elevation for a more dressed-up look.

Don’t: Go too dainty here. Cargo pants are meant to look a little relaxed and rugged.

Skinny Pants

Skinny pants may not be the trendiest option anymore, but many of us still love the way they look tucked into boots or worn with long tops.

Best shoes to wear:

• Knee-high boots: Still one of the best options for tucking in skinnies.
• Ankle boots: Make sure they’re snug around the ankle for a smooth silhouette.
• Flats: Pointed-toe or almond-toe flats help balance the slim cut.
• Sneakers: Keep them sleek and streamlined.

Skip: Overly chunky shoes—they can throw off the proportions.

Kick Flare or Cropped Flare

These are a fun update to both cropped and flare styles, and they show off your shoes beautifully.

Best shoes to wear:

• Slingbacks: Feminine and flirty, perfect with this style.
• Heeled booties: Great for fall, especially if the boot hits just under the flare.
• Mules: An easy, breezy choice for spring and summer.
• Sandals with a little heel: Just enough to dress things up.

Watch the length: These pants are meant to hit above the ankle—your shoes will be on full display.

Joggers

Comfy, cozy, and yes—you can dress them up. Joggers have officially crossed into “real pants” territory in 2025.

Best shoes to wear with joggers:

• Sleek sneakers: Classic white or tonal shades work beautifully.
• Slides: Perfect for casual errands or a relaxed weekend.
• Low block heels: Yes, you can elevate joggers with a structured top and heeled sandal.
• Loafers: A little unexpected, but very polished.

Avoid: Anything too fussy—joggers look best when the whole outfit feels effortless.

The Best Shoes for Women Over 50 for 2025:

Now that you know the best shoes to pair with your favorite style of pants, take a peek at these posts to see some of my top picks!

Ballet Flats:

• Are Ballet Flats Back? How to Wear Them in Spring 2025
• Rothy’s Flats: Are They Worth the Investment?

Sneakers:

• Keds BlissWalk Sneakers Review: My Honest Thoughts
• Amazon’s Bestselling White Sneakers to Wear With Everything
• The Best New Balance Sneakers for Women Over 50
• Fantastic Retro Sneakers To Buy Now

Heels:

• Kitten Heels for Women Over 50
• 7 Must-Have Heels for Every Fashionable Woman
• The Best Block Heels for Women Over 50

Sandals:

• Best Vionic Sandals for Women
• The Best Sandals for Women Over 50
• Olukai Sandals: Stylish Support for Everyday Comfort
• Stylish and Affordable Sandals from Amazon You’ll Want for Spring

Boots:

• The Ultimate Guide To Wearing Boots with Jeans
• The Best Black Leather Boots for Women Over 50
• Affordable Leather and Faux Leather Boots That Look High-End 
• My Favorite Ankle Boots For Women In Stores Now

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Verse Of The Day

Matthew 21:13 (NIV)
¹³ “It is written,” he said to them, “‘My house will be called a house of prayer,’ but you are making it ‘a den of robbers.’”