Some of you may know that my relationship with straight jeans has been, shall we say, tumultuous. I’m a 30-something millennial. I had to do a whole jump and roll to get into the skinny jeans I grew up wearing. The lower the rise and the skinnier the fit meant you were right on-trend. So, when the straight leg jeans, the Mom jeans, the Dad jeans, and all the other looser-fitting styles came on the scene, you can imagine my hesitancy to get excited about them. If you also have had a hard time finding the perfect pair, I’m sharing a millennial’s guide to styling straight jeans.

If you’re transitioning your wardrobe to fall, this post has 10 fall essentials to have in your wardrobe.

A Millennials Guide to Styling Straight Jeans

How Should Straight Leg Jeans Fit

Before we get into how I like to style straight jeans, let’s talk about finding the perfect pair of straight jeans and how to get the right fit. I’ve tried several pairs now, and I think I’ve cracked the code on which ones look the best on my body type.

Find the right length

For straight leg jeans, you want to aim for them to hit at the smallest part of your leg, ideally between your ankle bone or one inch above.

Many retailers offer short, regular, and tall lengths to help you get the perfect length for your body. However, if a certain pair of denim jeans doesn’t come in varying lengths, consider looking at cropped options, if you’re more on the petite side.

It’s important to also consider what type of shoe you plan to wear with your jeans. I love to pair cropped style jeans with taller fitted boots.

If your goal is to lengthen your legs, then look for slightly longer pairs and wear them with a heel to give the illusion of more height.

The Stretch of the Jean

The next tip in this millennial guide to styling straight jeans is looking at the stretch of the jeans. I’ve found that non-stretch is more flattering, especially with higher-rise. They’ll maintain their shape better, and won’t have that whole saggy situation happening in the back. But if you want a little stretch, I recommend finding a jean with 1% elastic, no more than 2% for the jean to maintain proper shape.

If you’re a fellow millennial who loves jeggings, then know this will be a big adjustment going from stretchy jeans to something more structured. I like to have extra room in the waist to make sitting more comfortable. Most of the jeans I’ve tried have stretched slightly after sitting in them a few times, too.

Overall fit recommendations

The younger generation prefers baggier-fitting clothes, but I would recommend finding a pair that fits well in the waist. Look for styles that say “fitted” straight leg or just fit closer to the thigh instead of baggier. This will also help you avoid the “flat mom butt” look.

When you’re checking the fit, you also want to check the back pocket placement. If the pockets are too big or too small, too high or too low, it can change the shape of your hips.

Consider your proportions

Proportions are important when styling straight leg jeans. If your torso is shorter, choose a mid-rise option. However, if you have a longer torso, you can opt for a higher rise. This creates a classic, polished look.

If you have wider hips, you will most likely prefer a curvier fit, like the Abercrombie jeans I reviewed.

You also want to be sure your waist is accentuated at least somewhat when wearing straight leg jeans. Your shape can easily get lost in looser-fitting jeans. If you’re wanting to wear a looser-fitting top like an oversized sweatshirt or a tunic, leggings or straight leg jeans would be a better option.

To make sure your shape doesn’t get lost with your straight leg jeans, you can use these styling tips:

• Front tuck your sweater or tee
• Wear a cropped shirt that meets at the top of your jeans
• Wear a fitted top or bodysuit
• Fully tuck in your shirt

Shoes To Wear With Straight Leg Jeans

Gen Z loves a chunkier-style shoe. But for millennials looking for a more classic look, here are a few shoe options to wear with straight leg denim:

• Flats
• Loafers
• Slim-fitted booties or ankle boots
• Low-profile white sneakers
• Skinny-strap heels
• Nude heels

To accentuate your length, style a pointed or almond-toe shoe with your jeans. And don’t be afraid to embrace bright colors!

Shop Shoes

What To Wear With Straight Leg Jeans In Your 30’s

Here are a few outfit ideas to get you more comfortable wearing straight leg jeans. I bet you have most of these items in your closet already!

Straight Leg Jean with a Bodysuit and Blazer

Shop the Look

The first look in this millennial guide to styling straight jeans features a boyfriend blazer with a bodysuit. An oversized boyfriend blazer is on-trend right now, and you can balance out a shorter torso with a longer piece like this.

Make sure to pair it with something fitted underneath like a bodysuit or form-fitting top to keep your shape. If you have a longer torso, a cropped blazer can help you look more proportioned.

Straight Leg Jean with a Cropped White Top

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The next look is a cropped white top with light wash straight leg jeans. If you’re wearing a peplum-style top like this one, you want to make sure the end meets at the top of the jeans. Because the top isn’t technically form-fitting from the ruffle at the bottom, it has the potential to lose your shape, if it doesn’t meet at the top of your jeans. I finished the look with quilted sandals that dress the look up a bit. This would be a cute and casual date night look.

Straight Leg Jean with a Tucked Sweater

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Another option for tops to wear with your high rise straight leg jeans during the colder months is pairing them with a sweater. This is the ultimate fall uniform! For chunky sweaters, be sure to tuck it in, or give it a front tuck, to balance out the overall look.

If you’re worried about the sweater adding extra bulk when you tuck it in, just tuck the very bottom of it slightly inside your jeans. I finished the look with a pointed toe flat to elongate my legs. *Peep baby Josie. 🙂

Straight Leg Jean with a White Button Down and Silk Scarf

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You can’t get much more classic than a white button down styled with a scarf. This would be a great casual Friday office look. I don’t have a scarf technically on in this photo, but you can drape it around the collar of your button down and tie a knot at the end to let it loosely hang around your neck. Complete the look with one of my all-time favorite fair of loafers. Such great quality and incredibly comfortable!

Straight Leg Jean with a Fitted Turtleneck Sweater

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The next look in this millennials guide to styling straight jeans is a fitted turtleneck sweater. You can either tuck in or leave untucked. Because it’s close-fitting to the body, your shape won’t necessarily get lost with this type of fit. You just have to watch where the sweater lands on your waist or hips. If it goes past around the tops of your thighs, then it might be better to tuck it in. That way your waist doesn’t look elongated.

Straight Leg Jeans with A Cropped Floral Top

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For a feminine look, pair a cropped floral top with a fun pair of heels. These heels run small, so I recommend reading this review on them if you’re interested in the purchase! This outfit would be perfect for date night or a dinner out with the girls.

Straight Leg Jean with a Trench Coat and Flats

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A chic and modern look to wear out shopping is pairing a trench coat with straight leg jeans. This would also make a great travel look when pairing with comfortable flats or white sneakers.

Straight Leg Jean with a Graphic Tee and White Sneakers

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For the ultimate edgy-cool look, pair a graphic tee and white sneakers with your straight leg jeans. If your graphic tee isn’t fitted, do a simple front tuck. A good pair of white sneakers are a great investment shoe because they pair well with denim, skirts, and dresses. I love wearing dresses and sneakers when we’re exploring a city.

Straight Leg Jean with a Moto Jacket

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The last look in this millennials guide to styling straight leg jeans is the perfect fall and winter look. A moto jacket is made for straight jeans because of its cropped fit. They’re also usually a more form-fitting jacket. Finish the look with neutral booties for a fun and casual date night look.

Hopefully this helps in your quest for finding the perfect pair of straight leg jeans!

Do you have a favorite pair of straight leg jeans? If so, where are they from? Let me know in the comments below!