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What shoes to wear with straight and wide-leg pants and jeans + 15 Outfit Ideas

Jan 19, 2022

What shoes to wear with straight and wide-leg pants and jeans + 15 Outfit Ideas

Happy Wednesday, friends!

Halfway through the week! This is the first week of January where things are finally feeling somewhat back to “regular programming” and it feels good to start getting back into a routine after returning from Cabo. We had the best time and it felt good to get away, and also so good to be back home with our Junebug.♥️

Today’s post is a highly requested one! How to style NON skinny jeans/pants and the best shoes to pair with them! It seemed like overnight denim styles other than skinny jeans became popular and the spectrum of style variations became endless — wide-leg, straight-leg, girlfriend, boyfriend, mom jeans, dad jeans. (Remember when it was JUST skinny jeans?) It seems like the straight and wide legs in particular are what leave everyone with the most questions on how to style!

What shoes to wear with straight and wide-leg pants and jeans + 15 Outfit Ideas

I love that both straight-leg pants and wide leg pants can look both vintage-inspired and elevated. The fit/silhouette works for so many materials — denim, chino, knit, linen, cotton — making them great for every season. I love dressing them up or down as well.

Don’t get me wrong, I’m still team skinny jeans and still believe they are a wardrobe staple (especially for Chicago winters–because nothing else tucks into tall boots!), but I also love both straight and wide leg styles. (Switching up your denim style can make you appreciate the rest of your wardrobe in a whole new way, too!)

That being said, initially branching away from skinny jeans can be a little intimidating — it can take time to find the best style, fit and brand for you — and then you have to experiment with which shoes to pair with them. So if you’ve been looking to take the straight-leg pant plunge or are searching for ideas on how to style the pair you already have, this post is for you! I dove into the archives and rounded up 15 outfit ideas with straight-leg jeans to highlight ways to style them as well as my favorite shoes to wear with them. Let’s jump in!

Tips for styling straight leg + wide leg pants and jeans: 

Explore different lengths + fits of pants: 

There are many different styles of straight and wide leg pants! Some straight legs have a slimmer leg, some have a tapered leg, some wide legs are a slight flare, others are super wide–you’ll have to experiment with what feels best to you! A jean like the Everlane Cheeky jean or Madewell stovepipe, or Madewell vintage straight, which have a slimmer straight leg, might feel more approachable to you than say, a Levi’s 501 jean, where the leg is a bit wider. Both are considered a straight leg, both are great,  but you might feel more comfortable in a slimmer leg, especially if this is your first foray into non-skinny jeans!

Length makes a huge difference: a cropped length just feels more approachable to me than a full length straight. The full length straight is definitely more trendy/Gen Z/90’s, and that’s awesome if that’s your style, but that’s not personally MY style and is definitely more of an edgy/trendy look, whereas my style is more classic. If you are like me, you’ll probably find that a cropped style may feel more “you” and also feels much easier to style with booties. (Which brings me to my next point that we’ll get to in a second).

If you aren’t sure of the right length for you, try rolling your jeans at the ankle. I have also created my own raw-hem jeans by taking off an inch or two with some scissors. I love a raw-hem look, and this is very easy to DIY, but you could also take your favorite jeans to a tailor if you have an existing pair you love and just want to hem. You have a lot of options!

Tips for Styling Straight and Wide leg pants with booties:

Tip #1: 

When styling a bootie with straight or wide-leg jeans, my tip is to ensure the bottom of your pants hit right where the top of your boot hits, or even leaves a little tiny bit of room in between. You don’t want TOO much room, but a little bit is good!

Tip #2: 

AND/OR ensure you are wearing them with a bootie that has a higher shaft and is slim around the ankle. This will ensure that it’s a flattering look and won’t make you look like you have odd cankles or tree trunk legs.

Tip #3: 

Sometimes you can get the shape of the pant/bootie right, but the color scheme is off. Try playing around with the color of your bootie based on what you’re wearing. I find that a color scheme here is best. A camel sweater with jeans and tan boots, or a tan sweater with black pants and black booties (with black socks, if needed). You can use the same approach you would with tights–if there’s too much color-blocking, it may look funny. Try going with a more minimalistic color scheme if you can’t put your finger on why your outfit looks off. Don’t be afraid to mix and match–try a different wash of jean, a different shade of top, a different color of pant, a different colored shoe, etc!

Troubleshooting: 

Some common reasons your outfit might not look quite right:

When the shoe and the pant leg are the same shape–that’s when it feels odd to me. (I.E. tree trunk scenario). OR, if the shaft of your bootie is cut too low and too much of your foot is showing–that can also look strange. Or you may find that you need a shoe with a bit of a heel, or a different shaped toe, or like referenced above, a different color! You may need to try a different bootie. Absolutely keep playing around–it may take a few tries to get it right, but you’ll soon get the hang of it!

What shoes to wear with straight and wide-leg pants and jeans + 15 Outfit Ideas

(Everything in this photo is old so can’t link–so sad Everlane doesn’t make these booties anymore!) 

Can you wear socks with booties to keep ankles warm? 

An equally as popular question from those who live in colder climates–can you wear socks to keep exposed ankles warm? Yes! You absolutely can with heeled or flat ankle booties.  I just choose sock that goes with the color scheme of my outfit. Let’s go through some example scenarios:

Sometimes that will be in the same color as my pants (i.e. black socks with black pants), other times that will be the same color as my top (grey socks with a grey sweater) or the same sock color as my booties (i.e. tan socks with tan booties). You may have to experiment with these three options to see which one looks right–it will depend on the outfit!

I recommend going with a wool sock that isn’t too thick–as socks that are too thick won’t look flattering and will give you cankles. I really like Smartwool socks–they’re very warm, but not bulky and they hold up really well! Amazon also has tons of neutral sock options with great reviews if you are wanting a little more bang for your buck!

Shop sock options here: 

What To Wear With Straight-Leg Pants + Outfit Inspiration

Straight-Leg Pants with heeled ankle boots:

Straight-Leg Pants with heeled ankle boots | What shoes to wear with straight and wide-leg pants and jeans + 15 Outfit Ideas

ABLE Top (TTS, wearing small) // ABLE Belt (TTS) // ABLE Booties (TTS) Use code JESSKEYS10 on almost all ABLE purchases for 10% off // Levi’s Jeans (TTS)

Transitional Ways to Style a Blazer | What shoes to wear with straight and wide-leg pants and jeans

Old Blazer, Old Booties, Everlane straight-leg crops (TTS, wear 25) Everlane washable silk blouse,  Everlane Tote 

What shoes to wear with straight and wide-leg pants and jeans

Dudley Stephens Park Slope Turtleneck, Everlane Wide Leg Crops, Similar Sock Bootiessimilar headband 

ABLE Leather Jacket

ABLE Leather Jacket (sized up to M for a roomier fit), ABLE wide leg crops (TTS), ABLE Booties (TTS) **Use code JESSKEYS10 on almost all ABLE purchases for 10% off

wide-leg pants outfit ideas

LOFT Pants, (Run TTS if not SIGHTLY big. Wearing small. See more ways to style them here), Sezane Top (TTS, boxy fit. See how I styled it in Paris here!) Sweater blazer: Mine is the J.Crew Sophie blazer which they have discontinued and they’ve replaced it with the new iteration: The Eloise sweater blazer. Also super cute and versatile! ABLE Booties (TTS) **Use code JESSKEYS10 on almost all ABLE purchases for 10% off

Straight-Leg Pants with flat ankle boots:

best shoes for straight leg jeans

Similar sweater, Madewell “Perfect Vintage” Jeans (TTS, but if you’re on the fence, go up a size if you prefer a roomier fit), Similar boots, Similar scarf

best shoes for straight leg jeans

Old jeans (similar here), old Chelsea boots (similar from Madewell here), socks, trench (mine is very old but linking this year’s version–it runs oversized in my experience!), old sweater. 

Straight-Leg Pants with Sneakers:

Straight-Leg Pants with Sneakers

Everlane cropped straight leg pants, Similar T-Shirt, Everlane Sneakers

Straight-Leg Pants shoes

Similar Pants, Old Shirt, Ray Ban Sunglasses, Tretorn Sneakers

Straight-Leg Pants outfit inspo

Everlane Jeans, Similar T-Shirt, Everlane Sneakers

Straight-Leg Pants with Loafers:

Straight-Leg Pants with Loafers

ABLE Sweater,  Madewell Jeans (run TTS IMO- love the dark wash!), Gucci Loafers (go one size down! I’m usually a size 8 and I got the equivalent of a 7), Ray Ban Sunglasses, Old Scarf, ABLE Backpack Purse (use code JESSKEYS10 for 10% off!)

what to wear with loafers

LOFT Pants (Run TTS if not SIGHTLY big. Wearing small), J.Crew Turtleneck (TTS), Gucci Loafers (I also love the Sam Edelman loafers for a more wallet-friendly alternative!),  Similar Cardigan

Straight-Leg Pants with Flats:

Straight-Leg Pants with Flats

Similar Sweater, Everlane Pants (TTS), Rothy’s Shoes: c/o (I went with my normal size but size up if you’re in question), ABLE Maha Leather Jacket, (Use code JESSKEYS10 for 10% off! I sized up so it’s roomier but it’s TTS.), Similar Scarf, Ray-Ban Sunglasses, Similar Headband

What shoes to wear with straight and wide-leg pants and jeans

Sezane Sweater (ordered my regular size but size down for a slimmer fit), Similar Levi’s Jeans, Schutz Ballet Flats (TTS), Similar J.Crew Coat that i also have and love!

wide leg pants outfit ideas

LOFT Pants (Run TTS if not SIGHTLY big, Similar Blazer, Everlane Silk button-down (my exact one is years old but this one is their latest iteration!) Rothy’s Shoes: c/o (I went with my normal size but size up if you’re in question)

What shoes to wear with straight and wide-leg pants and jeans

ABLE Shirley Utility Jumpsuit (TTS), ABLE mules (TTS) Use code JESKEYS10 for 10% off your ABLE order!

I hope this sparked new ideas for shoe pairings with your favorite straight-leg pants!

You might also like: 

Two Pairs of Super Comfy Works Pants + 8 Ways To Style Them!

What I wore in Paris: Outfit Recap!

5 cute and comfy fall/winter outfit ideas 

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