Levi’s are back in a big way, proving that a classic jean never goes out of style

Here’s my ultimate fashion rule (ready for it?):

Wear whatever makes you feel good.

Yep, that’s the rule. Wear what you feel good in and sometimes that means the same pair of cozy sweatpants and stained oversized hoodie you’ve worn for the last three days (fine 4 days). You need to feel good, and if it’s comfort, then it’s comfort. But sometimes, comfort and style can meet. No, really. It’s called “denim.”

Denim today is diverse! There are so many styles, washes, cuts, prices and ways to style them. I believe that everyone can wear denim. As for rules? meh – every ‘body” can wear every style, it’s all about how you feel in them.

Skinny Denim:

This is kind of my favourite style of denim. It is a classic and wardrobe staple. Even though 16 years ago when I bought my first pair of skinny jeans, I was like “what in the world are these?”

The Rocket Skinny by Citizens of Humanity are my ultimate favourite skinny jean

What to look for: look for one with stretch and structure because skinny denim are meant to hug you in all the right places. You want the denim to be thick enough to last but also to have enough stretch for the comfort factor and to avoid bagging at the knees or sagging on the bum area. A dark denim is a classic and can be easily dressed up. I love a mid to high waisted skinny jean as it extends your leg line.

Favourite way to style: they work with everything but I love adding a tall or an over the knee boot with them for fall and winter, or a pair of heels to make them work for a night out.

Investment Level: $$$$, this means that I would invest in the higher end of your budget for a good pair of skinny jeans, because I do believe they are a versatile wardrobe staple. You want a good quality denim that won’t easily rip on the knees either (at least not unless you want them to!)

Best For: EVERYONE

Shop my favourite picks for skinny jeans:

Boyfriend Denim:

Think of stealing your boyfriend’s pair of jeans that just magically fit perfectly, that’s the boyfriend jean. This style of denim is loose fitting, slouchy, and relaxed often heavily distressed (yes, Dad – I paid money for the rips).

These boyfriend jeans by AG have been well worn

What to look for: I like a thicker denim for this look, so it’s not too flimsy. It doesn’t have a lot of structure which is why a thicker denim is helpful to add structure. Look for the fit to be around the mid waist, so it sits just at your hip and then goes straight down from there.

Favourite way to style: It is a more relaxed style of denim which is why I love to keep my look with it as casual, yet polished. A pair of flat, belted and a sweater with a French tuck goes perfectly with a cuffed boyfriend jean.

Investment Level: $$$, this means that they are worth spending a little more on to get a good quality denim. I think the are meant to be your most comfortable go to pair of jeans.

Best For: All body types

Shop my favourite picks for boyfriend jeans

Mom Jeans:

I’ve already shared why I love these controversial denim style on my post here. They are also commonly called ‘balloon leg’ jeans. They sit higher on the waist and have lots of room through the hips, butt and leg area.

These mom jeans are from Zara Spring 2020

What to look for: Look for a pair that is a solid colour with no distressing or rips. Also look for a pair that slightly tapers at the ankle so you can roll it the cuff.

Favourite way to style: I love wearing these with a either a fitted bodysuit or a cropped sweater and even a pair of heels because it creates an unexpected look of dressing them up. But I’m also happy pairing them with birkenstocks and a t-shirt.

Investment Level: $ because these are a trend and may not be something that sticks around timelessly. They are definately more on the casual side, so you aren’t getting as much multi use out of them to justify spending a lot.

Best for: Moms, sorry young people, hands off! I’m joking, I’m just trying to take fashion back. But they do require someone who is comfortable with the style of them as they are more about comfort and trends than they are about being flattering.

Shop my favourite picks for Mom jeans:

Boot/Flare Cut:

I’m going to be controversial here, ready? These are my least favourite style. I mean, the 90s were great for so many reasons, but this style kind of lacks versatility. It’s mostly because I’m very tall and if the denim isn’t long enough, then it looks weird. Frankly all I call think back to is “floods!”

What to look for: Look for a structured denim that is high waisted and that the length almost skims the floor when you wear it with shoes. Buy them in a dark wash, and they can create the illusion of length for shorter frames. If you have wider shoulders or hips, or even a larger bust, then the wide leg could be a good option to balance out your frame. Here are some women who rock this look: here and here.

Favourite way to style: If I had a pair then I’d wear these in a dark denim, with a stiletto heel and a tucked in silk blouse. It’s actually a beautiful, classic look, but frankly I’m not getting a ton of wear from them so I haven’t yet bought a pair. But I would consider getting them in a white denim because the look lends itself to be less denimy and more classic.

Investment Level: $, because these are my least favourite style, I wouldn’t spend a lot. They seem to try to be making a comeback after almost 15 years, but they aren’t something personally I am looking to invest in.

Best for: Shorter frames and anyone who feels amazing in them!

Shop my favourite picks for boot cut jeans:

Straight Leg:

Straight leg jeans are the ultimate classic because they have an easy, effortless look. They fall between a skinny jean and a boyfriend jean. They are defined as having the width of the hem straight from the hip to the ankle.

Another favourite from Citizens of Humanity

What to look for: look for a pair that fits well at the waist and hips and sits mid waist. A medium colour wash makes it a classic look.

Favourite way to style: Think french girl style when you style these. A tucked in sweater and a pair of flats make this a classic staple. I also love pairing them with a pair of ankle boots that are begging to be shown off. But like any classic jean, a pair of heels and a classic button down can’t go wrong.

Investment Level: $$ because these are a classic jean and never really ever go out of style.

Best for: hmmmm, this one is hard. But I’ll go with – YOU!

Shop my favourite picks for straight leg jeans:

Wide leg:

Ok, I may have confused you a little with these. These are similar to the bootcut/flare jean but they are actually wide right from the hips all the way down.

The Denim Forum from Aritzia has a great line of affordable denim styles

What to look for: Have some fun and look for a culotte leg, which is wide leg and cropped above the ankle. If you do opt for a cropped leg, then look for a higher waist pant to help elongate your leg line.

Favourite way to style: Oh let me count the ways for these jeans. For a long time, I either wore heeled sandals or flat slides, but as I’ve grown more comfortable with them, they are versatile enough to dress up or down.

Investment Level: $$ because these are a trend and may not be something that sticks around timelessly. They are definately more on the casual side, so you aren’t getting as much multi use out of them to justify spending a lot.

Best for: Whoever wants to wear them!

Shop my favourite picks for wide leg jeans:

This Post has affiliate links where I earn a small commission from items purchased.