Leggings can have a very love hate relationship with the fashion world. Many fashionista’s don’t like leggings and would never wear them for anything but the gym, but I personally love leggings. I wear them the majority of the week, and know that many of you do too! They’re super comfy, they fit on those bloaty days, and they can be worn in so many different ways.

So to help all of you, my everyday kind of gals, I’m going to show you how to style 4 different kinds of leggings outfits, that’s right, 4! Each look, casual, festival, work, and concert/night out, has a few different tips for styling leggings for each occasion. This is a longer post than I normally would do for a fashion post, but it’s jam packed with lots of tips for you. Please let me know in the comments below if you like this style of post, or if you prefer something shorter that is easier to look over during your busy days.

Casual Leggings Outfit

Leggings are my go to for a casual look. They’re versatile, comfortable, and great for running errands.

Wear a Graphic Tee

When styling a casual leggings outfit I always opt for a graphic tee or flowy tank. A graphic tee is an easy go to when you’re on the go and with a few simple styling tricks you can make that baggy tee go from frumpy to fabulous.

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The 3rd Piece

For this outfit I used a long comfy vest as the 3rd piece. It has a few pockets which are really nice to have when out and about, and it also has some great detailing with the buttons and hood.

Generally the #1 rule of leggings outfits is to keep a top piece long to cover your butt, but to be honest, I frequently break this rule when keeping it casual. Sorry, not sorry. I just feel like you have more wiggle room when you’re styling a casual outfit with more of an athleisure vibe. If this is the look you’re going for try layering a cute bomber jacket as your 3rd piece, and top things off with a cute baseball cap.

Keep the Shoes Casual

When styling a more casual outfit keep the shoes comfy and casual. Sneakers are your best bet but cute flats would work too.

I love these Converse slip ons. They’re comfy and give off the rocker, old school Converse vibe without being high tops. Another great choice would be some white sneakers which are so on trend right now.

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Work Leggings Outfit

Not all workplaces allow leggings, but if you have a more casual work culture take advantage of it and stay comfortable for your work day.

Button it Up

When wearing leggings for work you want to make sure the rest of your outfit is dressy enough to offset the casualness of the leggings. I highly recommend sticking to a button up top, and it must be long enough to cover your butt. There’s no breaking that rule when it comes to wearing leggings to work.

I love this INC one I found on sale for $7 at Hudson’s Bay. It’s a great length, fits well, and I like the panel that covers the buttons for a more put together look. I couldn’t find the same one, but I’ve linked some similar styles for you below.

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Shop Polka Dot Tights and Flowy Skirt - Happy Stylish Fit - Shop Instagram

Add a Dressy Versatile 3rd Piece

A blazer is a great go to when styling leggings for work, but I like to go a bit more adventurous and wear a versatile scarf. Blazers are great, and many offices require them, but I think there’s something so feminine and classy about a beautiful well made scarf.

I fell in love with this one from Aldo. I didn’t buy it at first, but I could’t stop thinking about it and rushed back to the store. Thankfully they still had one! It’s super soft and has such a beautiful pattern. It works great for outfits like this because you can wear it as a normal hankerchief scarf, toss it over your shoulders as a classy shawl which keeps you warm too, or you could tie it around your purse for some extra pazazz.

Wear Heels

Heels aren’t an absolute must, especially if you’re on your feet all day, but you should keep your shoe dressy and close toed to keep your outfit office appropriate. I highly recommend heels as they dress up leggings that much more, but if they’re not practical you could opt for some cute loafers or dressy flats.

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Festival Leggings Outfit

Festival season is here and why not wear some comfy leggings if it’s still not warm enough for shorts or dresses? They’re super stretchy so you can run around and dance your butt off without feeling too restrained.

Crop Top

Crop tops are a huge trend right now and they’re great for festivals. If you’re a little self conscious or want a more modest look keep the leggings high, and layer with a longer sheer top like the patterned one picture above.

Keep the Accessories Fun

I always love to stack jewellery, but festivals are a great chance to go bold and layer those jewels. Try statement earrings with big bracelet stacks and a fun boho scarf like I did above. You could also layer long necklaces, or try a fun body chain.

You don’t have to stick with jewellery for fun accessories. Try some fun hair pieces, or my favourite, fun braids. You could also wear a super cute cross body bag too.

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Strappy Shoes

Strappy shoes are fun for festivals, but the most important thing is that they’re comfortable and secure. There’s nothing worse then wearing painful shoes that ruin your fun festival vibes. Make sure you can wear your shoes for long periods of time with no issues.

These wedge sandals are super comfortable for me, someone who wears heels frequently, but you could also style this festival outfit with some fun gladiator sandals or even some fun cage detail booties like the ones I’ve found below.

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Night Out/Concert Leggings Outfit

When dressing up for a concert or night out I like to add a bit of edge, but you could easily swap these items out for something a bit more glam if that’s the look you’re going for. Instead of the tshirt you could wear a flowy off the shoulder top, or even a crop top with a cute little jacket.

Detailed Leggings

Instead of opting for your usual go to black leggings try some with added detail. It’s hard to see in the pictures, but these leggings are actually slightly sheer leather type leggings with a cute lace detail. Something with sheer panels, cut outs, or lace up details are a great way to add some sex appeal as long as they don’t look too much like workout leggings. Finding some with nice details like gems or studs are another great option.

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Go for a Bold Lip and Blinging Accessories

An easy way to instantly make your look evening ready is to go for a bold lip. It looks great, and gives you that boosted confidence that comes from a great bold lip colour.

Give your look that fun party vibe with some sparkle. I’ve been loving this jewelled choker from Aldo, but you could also opt for a great pair of statement earrings, or a big statement ring.

Wear Heels

Again, this isn’t always practical, but a heel instantly brings your look from day to night. If heels just don’t work for you I recommend trying a bootie which can be more comfortable, or an over the knee flat boot.

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There ya have it, lots of tips for styling 4 different kinds of legging outfits. As I said i the beginning this kind of post is a little long, so thank you for sticking to the end! Please let me know your thoughts below if you like this longer type of post, or if it’s easier to read small amounts of information if I break it up into separate posts. Stay tuned for Friday’s tutorial where I’ll show you 3 different fun braided hairstyles for festivals and concerts.

xo Jannine

How to style leggings for any ocassion. Styling tips for a work leggings outfit, festival leggings outfit, casual leggings outfit, and night out leggings outfit. Stay comfy and chic.

How to style leggings for any ocassion. Styling tips for a work leggings outfit, festival leggings outfit, casual leggings outfit, and night out leggings outfit. Stay comfy and chic.

How to style leggings for any ocassion. Styling tips for a work leggings outfit, festival leggings outfit, casual leggings outfit, and night out leggings outfit. Stay comfy and chic.

How to style leggings for any ocassion. Styling tips for a work leggings outfit, festival leggings outfit, casual leggings outfit, and night out leggings outfit. Stay comfy and chic.