8 Casual Outfits & How To Style Them Yourself




One of the most common wardrobe challenges women face is styling their clothes in new ways. I'm often asked how I know what works well together and my answer is simple—I have lots of practise. I've spent many hours with myself and my wardrobe and have over 10 years of retail experience. To get better at something, we need to exercise that muscle!


So, in an effort to help you with outfit styling, I've rounded up eight different outfit combinations for you to try recreating with what you own, to practise the art of outfit styling. You might love an outfit, or you might hate an outfit. That's cool! Whatever you end up loving is a reflection of your personal style and how you like to wear your clothes.


The below outfit combinations have been broken down into simple formulas that will help you replicate these outfits (or variations of the sort) on your own. I've included tips with each one to help you along with styling, but please keep in mind that your final look vs. mine is mainly dependant on the colour and fit of each item; my clothes are a reflection of my style and vise versa.


Plain Tee + Duster Cardigan + Jeans + Colourful Scarf/Neckerchief

The type of jeans you wear will dictate the overall vibe of this look - ripped are more casual and edgy and skinny/bootcut are more classic and chic. This look can be repeated with various scarves, jeans and t-shirt or cardigan colours!



Fedora + Button-Up Shirt (unbuttoned) + Plain Top + Neck Scarf + Wide-Leg Pants + Flats

The proportions of your unbuttoned shirt and wide-leg pants will have an effect on the overall vibe of the outfit. All of my pieces are loose and flowy because I wanted a more comfortable, relaxed look. Keep this in mind when pairing items from your closet together!



Fedora + Layered Shirts + Pendant Necklace + Boyfriend Jeans + Ankle Booties

The key to the layered shirt look is to play with proportions and layer a longer loose top underneath a shorter, equally as wide one. Think: loose, relaxed tops you feel comfortable in. Another element that aids in the a well-layered look is a curved hem. As soon as I added a white tee with a curved hem to my wardrobe (as seen here) - my layering game changed. The high neckline helps too because if you get double exposure - top and bottom - the whole look changes. Additionally, the outer layer also has a split hem, which is hella visually appealing with any hem for that matter.



Duster Cardigan + Plain Tee + Denim Skirt + Belt + Pantyhose + Cute Socks + Ankle Booties

Denim skirts exude a cool-girl vibe and can be worn a variety of ways - just like jeans. In the warmer months just before and after winter, you can get away with pantyhose and cute little socks (or OTK socks) to keep your legs and feet warm. The key to breaking up this look is tucking in your shirt and adding in a cool belt.

P.S. Coordinating socks that peek out of your boots is an easy way to take a casual look up a notch.


Choker + Graphic Tee + Blazer + Cropped Jeans + Loafers

Picking a tshirt that coordinates with the blazer (one or more matching colours) will pull the look together for something a little more chic.



Baseball Hat + Plain Tee (or Graphic) + Pendant Necklace + Utility Jacket + Jeans + Ankle Booties

Because this look is so simple, the jacket and shoes will set the tone. A structured jacket and studded boots make this look edgy and tomboyish, but a simple change to a brown boot and softer jacket would be a completely different style.



Fedora + Tank Top + Mock Neck (or Turtleneck) + Jeans + Booties

The key to pulling off the layered tank + long sleeve look is to ensure your first layer is fitted (especially under the arms) and your second layer is more forgiving.

When it comes to the colours of your tops, try mix-and-matching your options to see which ones you like best - and if you're not satisfied, hit up Pinterest for to find inspo on the colours you like and set out to find your dream combo.


Baseball Hat + Jean Jacket + Baseball Tee + Dressy Skirt + Sneakers

Matching a colour in your top to a colour in your skirt is always an easy way to look stylish. Here I matched tones instead of exact colours, and took things up a notch with coordinating socks as well. An edgy alternative would be to swap out the denim jacket and hat for just a leather jacket.



Thanks for reading! My advice to you for recreating these looks - or for simply upping your casual style game - is to spend some quality time with your wardrobe. You could start by trying to match what you have with what I'm wearing in the photos above - or you can stick to the bare bones of the formula and try a variety of different combinations to see which ones you like best. My best advice is to just have fun with what you have.


And if you're really stuck? Send me a message and we can get you booked in for a style session.

ClosettCandyy is a wardrobe consulting service created by Jesse Whale serving the areas of Kingston and beyond. Virtual sessions are available.
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