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3 Ways to Wear Straight Leg Jeans

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how to wear straight leg jeans

Stripe Sweater, similar (mine is old TopShop), also love this one | Straight Leg Jeans (my exact pair is old, but love these)| Gemma Mules, also here

Now that the polar vortex is behind us, I’m working on getting my styled 3 ways series back in action! Shooting outfits in the winter is just so hard, so I apologize if you missed them, but I’m not risking frost bite for a few photos, ha!

Earlier this year, I asked for post suggestions and one that I got was how to wear straight leg jeans. Honestly, it’s a great question. They can easily make your legs look short or give you an overall frumpy look, which is exactly what we’re going to avoid today.

My biggest tip for wearing straight leg jeans is to do whatever you can to elongate your legs. I personally find that ankle length straight leg jeans help make that possible by showing a little more skin. If they’re too long, that’s when you run the risk of making yourself look short and stumpy. If you’re on the shorter side, have your jeans hemmed if you’re finding that they’re too long. I’m 5’8″ so that’s rarely a problem for me—if anything, my jeans that are suppose to be long end up looking like ankle jeans, ha!

Another tip—opt for the high-waisted pair, they naturally give your hips, booty and waist more definition. Plus, the high-waist gives the illusion of longer legs. Don’t you love all these mind games I’m sharing today?!

Best Straight Leg Jeans

When it comes to buying straight leg jeans, I always suggest opting for a high-waist. It helps with making those legs look a bit longer and the high-waist also defines your waist, which gives some shape to what could be a very straight outfit! Here are a few pairs I love! I think you can go with either a light or dark wash—it just depends on what you’ll be wearing them for. I always go for darker if I want a fancier look and lighter for a casual look.


How to Wear Straight Leg Jeans

How to Wear Straight Leg Jeans with Flats

striped sweater outfit

Stripe Sweater, similar (mine is old TopShop), also love this one | Straight Leg Jeans (my exact pair is old, but love these)| Gemma Mules, also here

Flats can be tricky since they don’t naturally elongate your legs, but you can still make it work. When pairing them with flats, definitely make sure you’ve got the ankle length jeans! Imagine if my jeans were just 1-2 inches longer here? My legs would look so much shorter and frankly a bit awkward.

Opt for flats that aren’t too heavy or bulky either. Loafers are also amazing because they show more of your foot which again, naturally makes your legs look longer. I paired mine with these slides that are a pretty natural tone that blends nicely with my skin color. Again, we’re all about making your legs look long!

ankle jeans outfit

ankle jeans and sweater outfit

I went with a thicker sweater on top because I loved how these jeans, that are actually more fitted in the hip/waist area, look with front-tucked sweater. Cozy proportions in my mind!

I’d wear these for work days, casual days around the house or running errands! Basically my everyday uniform over here!

Pair with a Blazer for Girls’ Night or the Office

how to wear a blazer

similar Blazer (mine sold out), also love this one and this one | Black Tissue Tee, wearing a small | Straight Leg Jeans | Newbury Boots, also love these | Saddle Bag, also love this one

Okay, so depending on your office’s dress code, this may or may not work, but I also love this outfit for girls’ night. Girls’ nights are my chance to wear something a little edgy and cool that’s also a little nicer than I’d typically wear for mom-ing around.

For this look, I wore a pair of ankle booties. The key to pairing ankle booties is to show just a little bit of skin between your jeans and boots to break up the proportions. The exception to this would be if you were wearing sock booties which are fitted around your ankle and give you that needed contrast. Essentially, we just don’t want our legs to look like non-shapely logs. Showing that bit of skin does that!

winter blazer outfit

womens outfit idea for fall

I kept the top half of my outfit more fitted this time. I have a simple turtleneck tee on with this blazer that I adore! I have such a tough time finding blazers that I actually like because I have a long torso. Usually they make me look shorter than I am. This one is pretty long and isn’t too bulky. It even looks cute with the sleeves rolled once!

how to wear straight leg jeans

Lastly, I tucked this top in to give more shape to my body. If you have a loose baggy sweater paired with straight leg jeans and NO tuck, it just looks a bit frumpy. Tucking it makes your legs look longer, defines your waist and makes you look polished!

For Date Night

winter date night outfit

Cashmere V-Neck Sweater | Straight Leg Jeans | Strappy Heels, similar | Leopard Clutch, also love this one

Honestly, this outfit could easily be worn to girls’ night or work too. You could dress it up with a fancier silk camisole and leather jacket (ugh, I should have done that!), but I was cold, so I went with the cashmere sweater—always a classy option!

I love this cashmere sweater and it was only $100, which is pretty much unheard of for cashmere!

white sweater outfit

jeans and white sweater outfit

how to wear ankle jeans

Okay, but back to the jeans. I absolutely love how straight leg jeans look with strappy heels. They make your legs look super long and make you look so effortlessly chic. These shoes are Tory Burch that I found at Nordstrom’s Last Chance outlet a few years ago, but these are nearly identical!

Again, I tucked my sweater for waist definition! A pretty long coat would complete this outfit for date night, but again, totally forgot to put that on too.

Key Tips for Wearing Straight Leg Jeans

So, in review, I realized as I was writing this that there were x tips that I mentioned over and over again, so if you’re reading this on the fly, remember these things when styling your straight leg jeans.

  • Tuck or front tuck your top: this defines your waist and gives shape to your body to avoid looking frumpy
  • Wear shoes that elongate your legs: whether you’re short or tall, you can choose footwear that gives your legs the illusion of being longer! Strappy heels, pumps and loafers all do a good job of this!
  • Show some ankle: showing some skin or wearing boots that fit your ankle tightly will give your legs definition. Especially great if you’re wearing non-fitted ankle booties (like my second picture), as it breaks up the width of the boot’s opening and your jeans.
  • Get the right length: make sure your straight leg jeans are ankle length. Too long and you run the risk of looking like your legs are short and stumpy. Also, opt for high-waisted to get more length!

I hope that helps give you some different ideas of how to confidently wear those straight leg jeans that have been sitting in your closet. And, if you have any questions on styling, leave a comment and I’ll get back to you asap!

photos by Hannah Schweiss

BTW, 2 ways to style a teddy coat, and 4 ways to wear overalls.



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