Fall/Winter
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How to Wear Loafers & Flats with Straight Leg Jeans This Fall

Last week, we talked about what shoes to wear with flares and bootcut jeans this fall. I promised a similar post for straight leg jeans, but as I got further into the post, I realized it was just wayyyyyy too long.

And the fact of the matter is, you can wear pretty much any type of shoe with straight leg jeans… but not all shoes work with all straight leg jeans.

Since there are so many variables, I decided to focus this post to how to wear loafers & flats with straight leg jeans for fall 2022. I’ll follow up with posts on boots and sneakers next week.

How to Wear Loafers with Straight Leg Jeans for Fall 2022

First, let’s define our terms. Straight-leg jeans hang straight up and down the entire leg from hip to hem. They be relaxed and slouchy, or sleek and slim-fit; and they come in crop, ankle, and full lengths. (On the average woman, ankle length jeans have a 27″–29″ inseam. Shorter than 27″ is cropped, and longer than 29″ is full length.)

Mom jeans, barrel jeans, cigarette jeans, balloon jeans, and stovepipe jeans are all variations on straight leg jeans. (I explain all those terms in my post, Women’s Pant Styles and Hem Lengths Demystified)

Also, remember that body type plays into how straight leg jeans fit. I have wider hips and thin legs, so a slim straight style hangs straight on me rather than hugging my calves, but slim straight leg jeans look more like skinnies on women with larger legs. All that to say, you may have to try different styles to find the style that looks best on you.

SIZING NOTES: I’m 5’5″ and I usually wear a small in tops, a 28 or 29 in jeans, and a size 8 shoe. Gifted items are indicated by c/o; everything else I purchased myself.

Straight Ankle Jeans

Pairing straight ankle jeans with flats such as loafer mules exposes a few inches of ankle, which is flattering because it draws the eye to the slimmest part of the leg.

left: Frame Le High Straight Ankle (size 28) // similar loafer mules // Frame silk tee
middle: Frame Le High Straight Ankle (size 28) // Steve Madden mules // Gap Factory sweater
right: Fidelity Cher (size 28) // Dolce Vita mules // Equipment sweater

The jeans I’m wearing in this section have a 27″ inseam with a 14″ leg opening. I’m 5’5″, and they hem is just above the ankle on me.

I like this look, but I realize some women will feel like it shortens the line of the leg, especially when there is high contrast between the denim wash and the color of the skin.

One way to soften that line that is to wear jeans in a lighter wash that doesn’t create such a stark contrast, as in the outfit below.

Frame Le High Straight Ankle (size 29) // Steve Madden mules (8) // Treasure & Bond sweater (S)

The same general principles apply for loafers. The AGOLDE Toni Mid Rise Straight has a 28″ inseam with a 12 1/2″ leg opening, so they’re right in between the Frame Le High Straight (27″) and the AG Mari (29″). These are about as ankle length as ankle length gets for me!

AGOLDE Toni (size 28) // Vince Camuto Prenten Loafer (8)

I love this length and fit of jeans with loafers. There’s just enough space between the hem of my jeans and the top of the shoe in the back to give the eye a place to rest, but not so much that it shortens the line of the leg.

AGOLDE Toni (size 28) // Sam Edelman Christy (8) // Michael Stars Muscle Tee

Lug sole loafers are trending this season, and these work well with straight ankle and straight crop  jeans because the bulky shoe balances out the wider leg of the jeans.

Frame Le High Straight Ankle (size 28) // Me Too lug sole penny loafers (8) // Gap Factory cardigan (S)

If you don’t like the lug sole, the darker color with more foot coverage also provides some balance, but with a more elegant look.

Frame Le High Straight Ankle (size 29) // Jeffrey Campbell Velviteen Bit Loafer (8.5) // Treasure & Bond sweater (S)

STYLE TIP: You also want to pay attention to the length of your shirt when wearing crop or ankle length jeans. I usually front tuck or wear a shorter length to balance out the proportions.

Full Length Straight Leg Jeans

Wearing a full length straight leg jean can be tricky with loafer mules because of the high vamp. (The vamp of the shoe is the part that covers the foot.)

This AG Mari slim straight has a 29″ inseam with a 13″ leg opening, which is technically considered ankle length, but it’s a little longer than that on me.

You typically don’t want your straight leg jeans to break on top of the foot, but it’s okay if the hem touches the top of the foot. However, I don’t care for how the hem of these jeans tries to slide under the top of the shoe.

AG Mari in 15 Years Shoreline (size 29) // Dolce Vita mules (8) // Madewell sweater (S)

The solution? Wear these these jeans with shoes with a lower vamp, or wear a shorter jean with those shoes.

Here’s the AG Mari in a darker wash with a chunky loafer. While the vamp is slightly lower than the Dolce Vita mules above, so the length of the jeans looks good to me, I feel like the slim straight cut is off balance with the chunkier shoe.

AG Mari in 10 Years Highline (28) // Madewell The Bradley Lugsole Loafer (8) // Treasure & Bond sweater (S)

Here’s how the same jeans look with a pair of low profile loafers. The balance is better, but the overall vibe is very conservative and almost frumpy, and I still don’t like how the jeans touch the vamp of the shoe.

AG Mari in 10 Years Highline (28) // Jeffrey Campbell Velviteen Bit Loafer (8.5) // Treasure & Bond sweater (S)

Next, I tried the same loafers with a pair of more relaxed straight leg jeans. These are the AGOLE Lana Vintage Straight Jeans, and they’re a true straight. They have a 31″ inseam and a 16″ leg opening, and they’re more of a rigid vintage denim.

AGOLDE Lana Vintage Straight Jeans (size 29) // Jeffrey Campbell Velviteen Bit Loafer (8.5) // Evereve sweater vest (S)

I am not a fan of this combination because I don’t like how the jeans buckle on top of the shoe. Ideally they would be an inch shorter; I think 30″ is probably the length for a full length straight on me.

I also tried the AGOLDE Lana with the Madewell lug sole loafers, hoping for a better balance.

AGOLDE Lana Vintage Straight Jeans (size 29) // Madewell The Bradley Lugsole Loafer (8) // Halogen sweater (S)

I changed tops as well, but I just don’t know. I’m not feeling these jeans overall, although my opinion is subject to change without notice. I just like a slimmer, more feminine silhouette.

Straight Leg Jeans + Flats

Pointy toe flats and ballet flats work with almost every length of straight leg jean, but with these straight ankle jeans, I feel like the wider leg opening looks a little off-balance with the exposed ankle and more delicate shoe.

left: Frame Le High Straight Ankle (28) // Sam Edelman flats (8.5) // Madewell cardigan (S)
right: Mother Dazzler // Tory Burch Minnie (8) // Vince Weekend V-Neck (S)

I think I actually prefer these shoes with the longer jeans. Because of the lower vamp of the shoe, you still see some skin, and the full-length jeans make my legs look longer and leaner.

AG Mari in 15 Years Shoreline (28) // Sam Edelman Wheaton Pointed Toe Flat (8) // Roan + Ryan Arlo Tank (S)

And I also really like these jeans with these slender pointed toe flats, but this doesn’t look fashion-forward to my eye.

I’ll be curious to see if these more delicate styles are coming back. I hope so because I really like them. I realize they’re a classic style, and I can wear them if I want to, but I’m not feeling this quite yet.

AG Mari in 15 Years Shoreline (28) // Veronica Beard Champlain Chain Pointed Toe Flat (8) // Roan + Ryan Arlo Tank (S)

Here are the same shoes in black with the straight ankle jeans. I think they work okay since I’m wearing shorts sleeves, but I don’t know that I’d like them if I had more of my skin covered.

I feel like you need to balance the skin at the ankle with some skin on top — either arms or neckline. I also might like this outfit better with black jeans. It would look more cohesive.

Frame Le High Straight Ankle (size 29) // Veronica Beard Champlain Chain Pointed Toe Flat (8) // old ATM tee (M)

And finally, I tried the AGOLDE Lana with the pointed toe flats, just to verify what I already assumed to be true. I do not care for this look. The jeans are relaxed and almost sloppy, and the shoes are too precious by comparison. There is probably a way to juxtapose those two elements in a pleasing way, but I don’t think this is it.

AGOLDE Lana Vintage Straight Jeans (size 29) // Sam Edelman Wheaton Pointed Toe Flat (8) // Halogen sweater (S)

As you can see, there are a lot of variables at play when pairing straight leg jeans and flats. You really have to try things on and see how you feel about them. I also realize that what is pleasing to my eye may not be pleasing to yours, but these are all the things I consider when putting outfits together.

The good news is, once you find pairings in your closet that work, you have a formula you can wear over and over again and recreate in different ways.

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22 thoughts on “How to Wear Loafers & Flats with Straight Leg Jeans This Fall

      1. I still like them for ultra casual looks, but I feel like I’m moving away from them for the most part. I do love the raw hem, though. It adds a bit of texture and toughness to an outfit without being over-the-top distressed. And it is so easy to cut if you don’t like the length.

  1. Great post! I still love the way those Toni’s look on you, even though I recognize they are not the most current look. That said, I love those Lana jeans on you! Yes, I know you don’t love them, but before you return them, I’d try them with other shoes – chunkier loafers or sneakers. To me, the shoe you paired with them is too business-like, but I think that cut of jean is flattering on you! And so hipster!! You are making me want to try them (and fwiw, I noticed Nordstroms has a similar version with a 30 inch inseam).

  2. You sure do a lot of work on your post and much appreciated. 🙂 I agree with all you said in this post. I am very picky with what shoes, with what jeans, now that I’m not wearing my skinnies. I still have a couple skinnies that run more straight leg, so still will wear them. I found a pair of my old LOFT, dark wash I had put away that were mid rise, but like one oft the first skinnies that came out and they actually are more straight and I think they will work. 🙂 They look brand new. Boy, skinnies were so much easier. You just put on a pair of jeans and any shoe/boot you wanted. 🙂 I like the Evereve Agolde Toni on you a lot with the leopard flat. I wish they told the rise. They just say mid but some reviews people say they fit tight and like high rise. Did you get your normal size? The price has really gone down and they might work for me. Have a fun day. I like full days. I’m headed to the beach with some friends in my bible study. We do it annually for 1 day.

    1. Skinnies are versatile, for sure, but I don’t remember them being particularly easy either. Every different shoe seemed to require a different length of jean, and then the question was when to cuff or cut, etc. I can’t tell you how much traffic my post about how to wear ankle boots got b/c they were tricky to pair with skinnies with the various shaft heights and styles.

      Also, people were very reticent to try skinnies when they first came out. But it was so long ago, I think we’ve forgotten that.

      I’m afraid to give you advice on the Toni b/c the pair I have is a different wash and they may not have the same measurements as the pair at Evereve. I can tell you that AGOLDE no longer has the Toni on their website, so I think the style is discontinued. If you like it, you may want to grab it and give it a try. I still have mine, and I plan to wear them this fall.

      Have so much fun at the beach!

  3. I appreciate these posts because I am having trouble with full-length straight leg jeans. I did an inventory of my jeans, and I have several pairs of straight legs–more than I thought. Most are ankle-length. I even made a list of cut and length for each pair! It was helpful,and made me realize that I only have 1 pair of bootcuts, and they are a little too snug. So that’s a hole I have to fill! I have 2 pairs of flares.

    I am not crazy about flats, although I recently bought a red pair…actually they’re similar to loafers now that I think about it. I love loafers–never thought I would! I have a few pairs, but also would like some with the lug sole. I love them! Thanks for the helpful post.

    1. I think ankle length for straight leg jeans is the most versatile length. I don’t love the full length styles… of course that may change, but there’s nothing wrong with wearing the ankle length if you like them.

  4. Great post! Thanks for the reminder about what the vamp is on shoes. I also like to see more skin on my ankles and feet. Sounds like you have a busy day and night. Enjoy dinner tonight!

  5. Thanks for including all the inseam information. I just got a pair of straight Levi Wedgie jeans that are a 28 inch inseam. I’m 5’4 and they aren’t quite long enough on me to be full lenth but aren’t short enough to be ankle length either so I’m going to carefully cut an inch off and go up from there. I have a feeling I’m going to probably end up 26.5 for me to like them at ankle. And I bought these in a lighter wash with the intention to have these be my fall running about jeans. I’m still shopping for a darker wash bootleg.

    1. Thank you, Jody, I’m 5’4 as well…..so that helps me narrow it down!!! I’m trying to get a handle on the new jean styles!

  6. Very informative post Jolynne! I’ve always struggled with ankle length jeans in fall/winter because I feel like they look like highwaters (somehow this doesn’t bother me with sandals in summer). I notice this more with boot/straight ankles than skinnies. These pictures were a lightbulb moment when I realized the higher vamp of the shoes helps counter this (the loafers vs flats)! As to those baggy Agolde jeans, I think they’d look much better with heels. It would keep the leg line from looking short and wide, but would also make it more feminine.

  7. What an informative post and certainly lots to take in.. it’s never easy so this gives great direction! I don’t think I have as much issue with footwear as I like an ankle length which may require me to buy petite as I’m 5’2and 1/2 as I found out this week I’m apparently not 5’3 anymore 🤷‍♀️but for some reason I’ve never liked my jeans long.. I’m going to look for a higher shaft bootie for when it gets colder but for now the the mules and fashion sneakers will work! I’m still wearing skinny with updated shoes or jackets/ blazers and I’m also wearing slim straight and straight to change it up! I found a cute pair of flares at Banana Republic but needed a petite and they were cute! I’ll be staying away from the wide leg and long slouchy look… seems like the younger ones can pull that look off.
    As far as denim wash goes do you find the medium wash more flattering? For some reason I’m not a fan of the darker washes on me and like length I’ve always been that way!

    1. Yeah, I think I just discovered why I like lighter washes or darker ones with distressing. It makes sense, I just never thought about it before, but I tend to be slightly top heavy, with thin legs, and lighter colors tend to make you look bigger. If I wear dark on top, light on bottom, the dark helps the top recede a bit, and the eye is drawn to the lighter area. So as far as medium wash to be more flattering… I think it depends partially on body shape and proportion.

  8. I’m 5’0” and petite, currently I’ve been cuffing my longer straight leg jean so it shows my ankle with a flat sandal or mule. I feel like it looks good and in proportion to what I’m wearing on top. Is this (cuffing to shorten) okay to do or would I be better off and more “current” if I cut the jeans to above the ankle instead? We live in the mountains of Colorado and it’s already getting colder at night, sadly, feel like I won’t be baring my ankles too much longer! Thank you for all that you do, I’m 65 years old and have been following you for a number of years.

  9. Love this post! When you say cut your jeans, do you mean literally take a pair of regular scissors and cut? And how precise do you have to be? Thanks 😊

  10. Thanks for the informative post! I just can not embrace the long, full AGOLDE Lana jeans. I just see 90’s teen! Like, put a pair of Doc Martin’s with those jeans! 😂

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