The Best Shoes to Wear With Every Pant Style in 2025
I don’t know about you, but picking the right shoes to wear with different pants can feel like a puzzle sometimes. You get your outfit all together, look in the mirror, and something just feels… off. Nine times out of ten, it’s the shoes (or is that just me)! The truth is, the style of pants you wear really does determine what footwear works best. And in 2025, there are so many pant styles making waves—wide leg, cropped, flare, straight leg, cargo, barrel, and more. I’m breaking it down and taking the guesswork out of getting dressed.
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:
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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.’”
🙂I lov e all types of shoes. I can shop my closet and find almost all of these shoe types. It’s a problem!
🙂 Found it. Great ideas, thanks!
😊
I prefer a comfy low heeled sandal or dressy sneakers these days.
Love the bow mules and white flats with navy toes 🙂
☺️
Ok I’m giving in and trying some of those clear slides. They’re fab! Plus loving the “cloud” bag too!
Lol! I hope you like them.
🙂 Great information
🙂
Love those scalloped bow mules!
The link doesn’t work for the Kick Flare jeans in this article, ” Best shoes to wear”.
Can you please provide that info?
Ty
It was working earlier. I’m not sure what happened. Here is the new link: https://go.shopmy.us/p-16372024
🙂 Thank you for all the suggestions!
😁one of the best posts!! I struggle with picking shoes too!!!
😊 Great info on shoes, sandals, boots. Thank you Tania for all the work you put into these posts.
I just love your ideas! You have wonderful taste! I’ve shared your blog with my gurls in my book club! Thank you! Found it!😊
Thanks so much for sharing!!!
🙂Love all the shoes! Looking great!
😊 Thanks for the tips. In the summer I only wear sandals either casual or dressy depending on where I’m going. I like my wedge heel sandals too. I’m going to make notes for the rest of the year when I wear closed toe shoes.
🙂 Shoes can make or break an outfit.
I still love the twin sweater sets, and the bow tie shoes would be a perfect accessory. I found it. ( :
🙂 Found it!! Love the pink top with ruffles!!
🙂 Great suggestions. I still love my skinny jeans and hope they come back soon.
They are slowly coming back in style.
😃 good information
I really like the Brooklyn wide leg pants. In a prior post, you stated that you always size down in Athleta. The pants listed today are a size 8. Is that the correct size or a misprint? I’m trying to determine my correct size. Thanks.
I must have made a mistake. I bought a 6 in those.
Thanks for the info! Going to get them bought now!
😀 like the flats.
Thank you for a wonderful post! Such great information on shoe style! Appreciate all your effort!!
🙂
You are looking so slim Please share your diet. 😊
Hahaha! I loved the story of your daughter. I used to “grocery shop” at my Mom when I was newly married, in nursing school and BROKE! Her pantry and freezer saved us! Seems like a right of passage 😂
🙂 You are so full of knowledge about fashion. Over the years you have helped me out with my style. Do you remember or did you ever watch the show “What Not to Wear” I loved it. Grown kids are all the same. I remember my sister doing that (taking whatever food she wanted) in our Dad’s house after she had moved out. My poor Dad probably went to get something out for dinner and it was gone!
I think I watched every episode of that show.
😀. Appreciate knowing which shoes look best with all the different pant styles.
Good information! Thanks. 😊
found it and your posts are fun!! Top off white loafer is my fav!
😊
Lots of great shoe info. I’m all about my shoes! And I just ordered a pair of Sperrys! Love them.
🙂 found it
Ahhh shoes – wonderful shoes. Can’t ever have too many.
Found it. Great advice!
🙂
This shoe guide is so helpful! I’m going to file this away for future reference.
😊 Great information, Tania! Thanks!!
🙂 I frequently change out my shoes several times before I leave the house. Thank you for this
advice! Most helpful.
Thanks for the showing us which shoes go with different types of pants. 😊
🙂 found it. I love the leopard print sweater
😀!! this is the perfect post! I’m sure everyone one time or another has wondered what shoes to wear with a certain outfit. Thank you so much for sharing this! I learned a lot!
🙂A good reference post for the season!
🙂 Great article, looks of information
found it!
I like sneaks or ballet flats (with support in them)
😊 Thanks for this information it’s very helpful.
🙂 I often have difficulty matching shoes, I like the shoes in most all the pics of this blog!
Love the outfits! It’s good to know the type of shoes to wear for wide leg pants. 😀I found it!
I just had to have the J Crew outlet linen shoes with the bow and, at the same time, a pair of shorts and two tees jumped into my cart with them. I’m giving a heads-up that there’s an additional 50% off clearance for some items plus free shipping for today only.
I love it when they have a pop-up sale.
😀 I love the Sperry slim boat shoe.
🙂 Love the Bow Mule shoes. Those are super cute with a bow.
😊I tend to spend WAY too much time deciding what shoes look best
😀 Interesting story about your daughter robbing your pantry. Thanks for the very helpful tips and informative post.
🙂 I like your tip to wear clean not bulky tennis shoes to complete the look, do not wear our heavy running shoes which are not always clean!
😄. I love the dogwood necklace you have on in the cargo pants picture.
☺️ found it!
lots of great suggestions for shoes and what outfits they look good with. I ordered the Talbot’s sweater and vest. can’t wait for it to come.
☺️ Thank you for clearing up what shoes work best. I wear primarily straight legs and crops. It’s sandal weather here, so I’m ready.
😊
Such a helpful post!
🙂
This was SO helpful
😋 I like the pants that are roomy through the thigh and taper at the ankle. They look comfortable.
😊 Thanks for this post. Very good information because sometimes it is hard to decide what type of shoe to wear. The wrong shoe can definitely ruin a whole outfit!
:). Found it! Good tips! I never have the right shoes! Especially when traveling- I always pack too many!
🙂 Love that striped shirt.
😊. Like your Spring clothing
Found it! I have found ballet flats flattering and comfortable.
🙂Balance is the key
Good information!
Found it 🙂
😃great information. Thanks
Good information! :}
🙂 Those cargo pants are so cute and look comfortable….now not available until June.
🙂 Thank you for all the great information on which shoes to wear.
Adult children never really leave home.😏
🙂 This was a very informative post that I didn’t realize I needed until I read it!!
In fact, I jotted notes and have posted it in my closet for easy reference.
Cute story about your daughter-mine used to do the same thing and I even put things in the pantry that I knew she liked to surprise her.
That’s cute that you stocked it for her.
😊 Thanks for the suggestions!
🙂 I always appreciate help with shoes and different pant styles!
🙂 Good info. On a side note, two of your pictures showed tops that I purchased both this year and last: the textured tee (bought 2 colors) and the floral short ruffled sleeve. Love them!
I’m glad you liked them!!!
Thank you for these suggestions – something I will refer to again and again. 🙂
🙂 My best shoes are always “comfort” shoes. I hate my feet to hurt. Thanks for the ideas.
🙂 thanks for the recommendations!
🙂 I mostly wear my Ara sneakers, they are so comfortable!
I have always worn keds. The new keds I plan to buy. My favorite post is your Sunday posts on faith
Keep doing it .Brings peace and joy to my heart. Children grocery shopping at mom and dad’s is one thing my children have done(we have 5 children all grown now) It’s a joke between all of us. Keep doing what you’re doing ! 😊
🙂
I always struggle with what shoes to wear with each style of pants. Thanks for the tips!
😀thanks for the advise!
😊great ideas! I’m really liking the high waisted flare jeans on you! They don’t look the same on Amazon. How do you like them?
They fit great. I like them and kept them.
When my sister came to visit we both were wearing cargo pants just 2 different materials mine slick hers jeans! Yes we love them, me 69 her 67yrs old lol.
I will be looking at some dressy mules I think because I don’t have any. Thanks for suggesting.
😊Another great article!
Found it. Love the shoes. Shoes are my weakness. Always great to get new ideas
🙂 ah…shoes. I also love them! Especially now that I can find them reasonably priced on Amazon.
😊 thank you for the suggestions for all the types of pants!
🙂 Funny, my kids will be shopping at “Moms” store when they come home this weekend❣️
Found it! 😁
Love the casual look with the black joggers and tee with leopard cardigan!❤
Found it!
My daughter “shops” in my pantry, too!
😊 you always find the best shoes! Cute and comfortable! Just what I need being over 60……….🫢
🙂 You look great in the slim jeans!
😀 Great info, thank you.
😊I needed this information as I always seem to grab a pair of ballet flats
🙂 Shoes can really complete an outfit!
🙂 SHOES!! I love SHOES!! My sweet husband converted a room into a dressing room for me, complete with shoe racks. At one point he suggested that if I bought another pair of shoes, I should consider giving away a pair. So, when I did buy that next pair, he asked if I had chosen a pair to give away. I went to HIS closet and brought back a pair of HIS shoes and said, “These!”. He rolled his eyes and hasn’t asked since!
Molly, that is fantastic! That was a cute answer to his question.
😊 This post is one to keep for reference. I love the blue v-neck sweater & white jeans on you!
Found it! Picking the right shoes can be so stressful. Thanks for helping us gurls out!
😊 Very helpful!
🙂 Great post. Thanks!
Found it 🙂 Love the Ryka white sneakers. I find that brand so comfy.
Found it 😊. Good advice as always.
😃 Great information and very helpful.
😀Great post about proper footwear. I’m always working on this. Love the story about your daughter grocery shopping your pantry 😂 When my daughter was moving into her first apartment ,she was pilfering my silverware, unbeknownst to me at the time. Visiting her home now years later I’ve discovered my missing silverware in her kitchen drawers!😳 Kids!
I had two sets of silverware. She took one of them until she finally bought her own set.
🙂 Great post packed full of useful info. I didn’t like the wide leg pants at first but I’ve found a few pairs that work for me.
I’m like you. I like some of them better than others.
😀 I so appreciate the work you put into your posts. I struggle with choosing the right shoes to go with my outfits. Have a great day!
Found it 🙂 Like the loafers with jeans.
Thank you Thank you! This is very helpful, appreciate all of the suggestions.
:). I’ve avoided buying kick flares as I did not know what shoes to wear with them. Thanks for the informative post. I have an abundance of shoes and now I know what looks best with different pants.
Deborah, they are becoming some of my favorite to wear.
😊Thanks for adding the shoes to avoid with each style. Very helpful.
found it
Found it!
Great advice for shoes.
Found it! Cute shoes.
Thank you. Very helpful information. Balance is the key! 😊
🙂 this list is very helpful.
; )
😀 Very helpful post for all the different pant styles out there!
😊
Thanks for all the great shoe style advice. I’m loving the Sperry boat shoes.
I do too! I have never had a pair!
🙂
🙂 Shoes are always my problem because I need very supportive shoes for my problem feet. So, I do the best I can and select the pant to go with the shoes I can comfortably wear. I agree about your comment regarding the barrel jeans. I’ve seen them styled many ways and, on every shape, and it’s just not a flattering style. It’s one of those trends I won’t be participating in! Lol
FOUND IT! 🙂 Such helpful fashion advice! Now to put it to the test! 😉
🙂 My son does his grocery shopping in my pantry too!
🤣🤣
😁Great post!
😊The barrel jeans look great on you but not sure I could pull them off.
I’m not sure I can pull them off either.
You look fabulous & I’d be a happy girl when I am your size again. My hubby & I started carnivore 3 weeks ago. Love to know where you’re finding variety in your meals.
We actually keep it really simple. But, you can use crushed pork rinds for a coating to make things like fried chicken, salmon patties, etc.
😢🌿💜🌱🥗🥑🥭🥝🍏🍍🍉🍇🕊
😊Great post.
Found it 😊 Thanks for the tips. I often struggle with what shoes to wear with the different types of pants.
What a helpful post!! I always have found choosing the right shoes to go with various outfits (or pants styles) to be a challenge. These suggestions demystified it for me!
Yay! I’m glad it helped.
Found it. Good post and love the baggy jeans.
😃😃very helpful! With all
The new pant lengths it’s confusing to choose which shoe is right!
🙂 Was wondering about the joggers. Wore some yesterday.
😊Such a helpful guide. I tend to favor the straight leg pant with flats, sandals, or ankle boots in the cooler months.
I found it‼️‼️‼️😀😀😀😀
🌸🌺🌸🌺
😀Thanks for this post!
Found it!
Such a helpful post❤️ I am always guessing about which shoes to wear with my pants. Thank you!
Found it!
Such a helpful post❤️
🙂
🤗 😀. Love the “what shoes to wear” post.
🙂 Thank you for the great suggestions. I think kick flares are the hardest to pair.
🙂 Love your posts, thank you for sharing.
🌞 it’s nice to see the outfit with shoes. Lately my feet aren’t cooperating with my shoes.
😂 I loved the salt & pepper comment. That’s just the way our boys are.
Great suggestions.
🙂 Shoes are a challenge, especially finding something comfortable.
😊 great post. I always have difficulty choosing the right shoes
😊
First I’ve heard of the barrel pants.
Barrel jeans have been around since last year. But, I’ve not found a pair I love.
😊
This was a really useful post. One I will save for future reference.
😊Found it. Love the cargo pants. Thanks for the shoe info.
I’m glad you liked it.
😀
Lots of great shoe choices!
😊 Thank you for his information. Takes the guessing out of what shoes to wear.
It can be hard to figure out. I hope this helped.
😊 i really like those cargo pants
😀 great post! Very good info!!
😀 a great blog to save, thanks!
🙂 Great post. Picking the right shoe is tricky.