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11 Ways to Step Up Your Leggings Game (and Get Away with Them at Work)

Hello my beautiful readers! The time has finally come for you to view The Leggings Lookbook - which I've made readily available within this post or at the link above.

This was the most popular Lookbook ya'll voted for earlier this year, so I appreciate your patience as I launched the Layering Lookbook first; it was only right with the weather we were having!

This lookbook is a little different from the rest (doesn't it feel like I say that every time?) and moving forward I'm hoping to continue with the way things were done this time around! In most of my past lookbooks I've used my own clothes because it allows for the most versatility and ease when styling outfits. However, this isn't the best option for you - my readers - because most of my items are over a year old and not readily available for you to purchase. So, what I've done here and what I'd like to do for the next little while is use some of the best resources Downtown Kingston has to offer and source my clothing from our local retail stores! Exciting right?!

You may have already seen online that this particular lookbook was curated using a collection of beautiful clothing and shoes from sister stores Fancy That & Roundstone.

Now in their 32nd year of business, The Fancy That Group has grown from one idea to three stores specializing in european clothing, stylish handbags and fashionable footwear.

In addition to their impeccable style and charm, the fabulous women who run the family business - Inger, Maria and Amanda - are three of the most loving, beautiful, and kindhearted people I've never had the pleasure of meeting. I'm so thrilled to bring you this collection of hand-picked quality clothing, styled with a focus on leggings to spark your imagination and get you excited for summer dressing.

In the gallery below I've included a full slideshow of the Leggings Lookbook, followed by an individual gallery of each outfit listed with the basic outfit formula for you to recreate. If you see an outfit or item you love, take a screenshot and show the ladies at the store when you pay them a visit! They'll be able to help you find everything you need.

P.S. Keep your eyes peeled on my social channels this week for a coupon code worth 15% off your purchase.

*If you're viewing on mobile, you can pinch to zoom in & use your finger to swipe.

Advice For Styling Leggings

As someone who doesn't wear and style leggings on the regular, I learned a thing or two from this experience I thought would be helpful in sharing for those who do (or would like to).

  1. Make a Commitment. If you want the luxury of wearing comfortable leggings for part of your everyday wear, my advice is to make the commitment to your wardrobe that you'll invest in the right pieces to make this a reality. I'm someone who prefers trousers and jeans to leggings, so I haven't made this commitment (which is part of the reason I sourced my clothing). You'll notice in all of the outfits I styled, every single top or dress is LONG - long enough to cover the goods. And that's because leggings AREN'T pants and I'm sorry but - no one wants to see your camel toe. If you're wondering why you can't style your leggings for something other than the gym or a casual look, maybe it's because of what you're working with! Which leads me to my next point...

  2. Prioritize Quality. I've found that styling leggings becomes easier once you have something of quality to work with. I'm someone who doesn't wear leggings on the regular, so I had to source mine from elsewhere. And as soon as I experienced what a quality legging feels and LOOKS like, I had no problem understanding the styles of tops and jackets that would look best. Fancy That/Roundstone has a great collection of quality leggings n a variety of colours and patterns, and I will be talking about my pair from Girlfriend Collective on the blog next week.

  3. Look for Variety. Through the experience of styling this lookbook, I've learned that certain styles of leggings are best for certain outfits. For example when wearing leggings under a dress, a thin pair is best to almost resemble pantyhose. And when wearing leggings as "pants," a thicker pair is warranted for obvious reasons such as camel toe and panty lines. And leather leggings are just really fun to wear.

  4. Mix & Match Highs & Lows. This is one of my favourite ways to style an outfit. An item classified as "high" is anything more polished, like a blazer, blouse or silk skirt. And an item classified as "low" is basically anything casual from your white tee, to a pair of distressed denim, or flannel shirt. Leggings are essentially considered a "low" so keep this in mind when styling. You can learn more about how to apply this trick to your everyday dressing here.

If you're a leggings gal and the above resonated with you, I recommend creating a Pinterest Board of Outfit Inspiration and Wish List of shopping items that you can slowly and intentionally purchase. This means not buying something just because you spent 3 hours shopping and it's "good enough." There's no race to building your wardrobe. A perfectly curated one that reflects your lifestyle and what you feel best in will take time to build.

Keep scrolling for a list of eleven different ways to step up your leggings game...

CASUAL OUTFIT IDEAS / Suitable for summer activities such as: bbq's, birthday parties, food dates, the carnival, farmer's market, music festivals, etc.!

1. Add A Pair of Patterned Leggings to Your Wardrobe

Outfit: Tie Front Top + Long Tank + Gingham Leggings (thicker material) + White Sneakers

Accessories: Neck Scarf + Straw Hat + Statement Earrings + Matching Nails + Lip

2. Wear Them With a Shirt Dress & Funky Shoes

Outfit: Shirt Dress + White Tee + Textured Cut-Out Leather Leggings + Patterned Heels

Accessories: StatementEarrings + Waist Belt + Matching Nails + Lip

3. Wear An Off-The-Shoulder Tunic & Ankle Boots

Outfit: OTS Dress/Longline Top + Thin Leggings + Ankle Boots

Accessories: Straw Hat + Statement Earrings + Beaded Bracelets + Tote Bag

4. Layer a Bright Knit Over A Long Basic (or Collared) Shirt

Outfit: Long White Tank + Thin Knit Sweater + Shirt Dress Worn Open/Utility Jacket + Textured Cut-Out Leather Leggings + White Sneakers

Accessories: Ball Cap + Beaded Bracelets + Pendant Necklace + Matching Nails + Lip

The necklace in this particular outfit is by Whitney Haynes Designs.

5. Wear Your Shirt Dress Open Over A Tunic

Outfit: Longline Top + Shirt Dress Worn Open/Utility Jacket (Rolled up) + Textured Cut-Out Leather Leggings + Cute Flats

Accessories: Fedora + Beaded Bracelets + Matching Nails & Lip

6. Style Them With A Long Top + Poncho

Outfit: Longline Top + Poncho + Textured Cut-Out Leather Leggings + Ankle Boots

Accessories: Fedora + Beaded Bracelets + Longline Pendant Necklace + Tote Bag

This fedora is available at Whit Kingston!

WORK OUTFIT IDEAS / Suitable for a work environment, interview, out of town shopping, fancy lunch, dinner, baby shower, date night, business-casual occasions, etc.!

7. Add A Longline Blazer To Your Wardrobe

Outfit: Longline Tee + Longline Blazer + Gingham Leggings (thicker material) + Mules

Accessories: Scarf + Longline Necklace + Drop Earrings

8. Layer A Vest Over A Long Knit Sweater

Outfit: Longline Thin-Knit Sweater + Longline Vest + Thin Leggings + Loafers

Accessories: Fedora + Scarf + Longline Necklace + Statement Earrings

9. Match The Colours in Your Patterned Leggings

Outfit: Longline Top + Longline Cardigan + Gingham Leggings (thicker material) + Loafers

Accessories: Neck Scarf + Layered Necklaces + Matching Nails & Lip

10. Dress Them Up in a Flirty Dress & Cute Shoe

Outfit: Polka Dot Dress + Thin Leggings + Cute Flats

Accessories: Waist Belt + Statement Earrings + Matching Nails & Lip

11. Style Them With a Classy Tunic & Blazer

Outfit: Longline Top + Longline Blazer + Textured Cut-Out Leather Leggings + Loafers

Accessories: Thin Waist Belt + Matching Nails & Lip


  • All of the beautiful clothing and shoes you saw were provided by Fancy That/Roundstone in Downtown Kingston! You can find them at the corner of Princess and King.

  • The earrings and necklaces that added the perfect touch to each outfit are by the very talented Sherry Jefferey. You can check her stuff out here and find her for sale at the Hochelaga Inn, or Kelly's Shop.

  • The pretty little beaded bracelets included in a few of the looks are from Beads by Meg, another talented local artist who makes jewelry.

  • My adorable, custom Tote Bag is by local Graphic Designer & Artist Taura Hanson of Art by Taura. Wait till you see how cute it is!

  • The oh so sweet ClosettCandyy Mug you may have seen is by the lovely Anna of Lettering by Rose.

Important To Note

These Lookbooks are not created with the purpose of making you want to buy more clothing or feel like your wardrobe is inadequate. They're created to inspire you to try new styling ideas, show you something you might be missing, and teach you that your clothing can be worn in a variety of ways and that in fact, I encourage you to spend more time wearing what you already own (as long as you love it) in different ways. We live in a world where the media tries to tell us we need NEW and we need MORE, but I'm just here to tell you to slow down, be intentional with your purchases, and get creative with your wardrobe.

Thanks for reading!

xo Jesse

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