Jean styles come and go, for sure, but honestly, I think the best game plan for “keeping up with changing trends” (we get asked so often, it deserves quotes, haha) is to find what jeans you love best and stick with them.
I still think it’s important to explore (I’ve tried on SO many jeans over the years), but what do I feel most myself and most comfortable in? Straight-leg jeans. They’re a classic fit and honestly so versatile. I don’t have to try hard to make them work, but I do get asked quite often which shoes work with them.
I get it. You don’t spend your days trying out a bazillion combos, so that’s where I come in to help. Here are my current favorite shoe styles to wear with my beloved straight-legs!
Jean Options: Here are few of my favorite straight-leg jeans. Size up for the non-stretch options here and TTS for the pairs with stretch. Levi’s 501 Original | Levi’s Wedgie Straight | AGOLDE Riley | Madewell Perfect Vintage Straight | Risen Straight-Leg (so comfy!)
Similar Top | Jeans | Sambas (or these)
The 10 Shoe Styles I Love To Wear With Straight-Leg Jeans
So, the main reason this can be a tricky undertaking is length of the jeans + the shoes you’re wearing.
Now, I say straight-leg jeans are versatile, and they truly are, but the thing is, you might have to A. have a few pairs in different lengths to accommodate your favorite shoes or B. decide you’re going to be on board with the full-length-jean thing right now… That works with a ton of different shoes.
The only thing with option B is that the overall vibe will be a little different than the vibe you get cropping your straight-legs just slightly above or right at your ankle. For me, I’m still liking both vibes, but I’ve been leaning more toward full length. I do love showing off my high-tops, though, so I keep the cropped options in rotation for mostly that reason!
This is why I do think it’s helpful to share lots of pics and options. I’ve got some of both below for ya!
1. Pointed-Toe Boots
Pointed-toe boots are some of my favorite shoes to wear with most jeans, but they look really great with straight-legs. I love them with any length straight-leg jeans, whether they’re a slim straight or a bit wider. The pointed toe really elongates the leg, especially with the full-length styles we’re seeing now.
Jacket (6) | Similar Jeans | Similar Boots | Similar Bag
Similar Tee | Jeans (29) | Similar Boots
Similar Sweater | Jeans (29) | Similar Boots
2. Chunky Lug-Sole Loafers
Lug-sole loafers are huge right now, and I’ve been loving them with all my straight-leg jeans for a few years now. I think the chunkier the loafer, the cuter they would look with full-length straight-leg jeans. I haven’t landed on the perfect combo yet, but I’m leaning toward black jeans and chunky white or taupe loafers.
Similar Blazer | Similar Tee | Similar Jeans | Loafers
Sweater (S) | Similar Jeans | Loafers
3. Low-Profile Sneakers
Sometimes low-profile shoes are a tougher sell for me, but I’ve discovered I love them especially with full-length straight-leg jeans I’m seeing more of lately. Adidas Samba sneakers (or similar pairs like this) look great under a bit of a puddle of a hem. Classic Vans slip-ons go perfectly with my cropped pairs of jeans OR with full length (you can see that here.)
Similar Top | Jeans | Sambas (or these)
4. Short Cowboy Boots
The key here with short cowboy boots is to let the hem of the jeans come out over half the front of the boots, then otherwise don’t worry about it. This one may not be for everyone, but paired with a structured blazer…I love it. The blazer balances out the Western-boot vibe that can lean almost costume-y sometimes.
Blazer (6) | Similar Jeans | Similar Boots | Bag
5. Mid-Top Sneakers
Love ’em or hate ’em, my Golden Goose Mid Stars have been one of my best shoe purchases ever. They look cool and have lasted for years. I love them much more than the low-profile GG options, but any mid-rise sneaker is perfect with ankle-length straight-leg jeans.
Sweater (M) | Jeans (29) | Sneakers
6. Retro Running Shoes
I wasn’t always for (actually for a while I was vehemently against) running shoes and jeans together, but as I saw more and more of this trend, I came up with some combos I do like for myself. I love retro-style running sneakers most, personally, and a fun pop of color is a bonus.
Similar Shacket | Similar Jeans | Similar Sneakers | Similar Bag
Similar Blazer | Tee | Similar Jeans | Sneakers
This pair of jeans above is a leetle bit of a wider-cut straight-leg (here’s a similar pair), but I think that works well if you’re gonna go full length + running-style sneakers.
I wouldn’t call this pair a wide-leg because of how it fits versus other wide-leg jeans I’ve owned (and honestly mostly disliked — I’m not a big fan of wide-leg jeans on my frame). This combo works well, though, and goes with just about any running sneaker you have in your closet.
7. High-Top Sneakers
Nike Blazer high-top sneakers are always a good idea for me. These work especially well with straight-leg jeans.
Sweater-Blazer | Tee | Similar Scarf | Similar Jeans | Nike Blazers
8. Slip-On Mules
Easy slip-on mules are a great option for the office if you have a casual Friday or casual work sitch. Mules fit with just about any leg shape, but I really love how it elongates the leg with a straight cut. These are my favorite style “dressy-ish” shoes when I don’t want a heel.
Tee (M) | Similar Jeans | Mules | Similar Bag
9. Any Kind Of Heels
Hi, date night! This is a fun, easy, cozy look for going out to a casual dinner, movie, etc. I’d also pop on this heels-&-jeans combo for brunch with friends.
Kitten heels are my vibe these days, and d’Orsay heels are always my go-to for a pretty flattering look on the foot. Heels look good with most jeans, but it’s nice to see them pictured with straight-legs since we’re talking about them. 🙂
Similar Cardigan | Jeans (29) | Similar Heels
10. Platform Sneakers
Platform sneakers are a newer addition to my closet, and I’m loving them for a classic look — but with an on-trend twist. Plus, it doesn’t hurt as someone who’s 5’4″ to have that added height. These work with my ankle/cropped straight-leg and full-length jeans really well.
Whew, friends. Hope this somewhat epic post proves helpful for our upcoming fall season, answering the age-old question of which shoes to wear with which jeans. I may dabble in other cuts for fun, but I’m still a forever a straight-leg-jean gal here.
If you’ve found any seriously comfy options out there lately, let me know! Until next time…
xo,
L
Would love for you to follow over on my Instagram, if you’re so inclined, for more outfits of the day, pet memes and motherhood musings from Portland, Oregon. xo
