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I have never really sat down and thought about my creative process when it comes to creating outfits. It wasn’t until I put a query out on Instagram and asked what kinds of things people would be interested in reading about that this became a forefront thought in my mind.

I think I would be intested in hearing about the method of getting creative with clothes. I have a lot of things I love that don’t get worn but I know I shouldn’t part with bc I always end up regretting the sale in 4-6 months. You’re so good at wearing things multiple ways, I feel like if you could talk about your creative process, it would be so helpful!

Charissa, @kalos_style

I must admit, I had to think on it for a while. I honestly didn’t really know if I had a method for creating outfits. I’ve been lucky in that I’ve always had an adventurous attitude when it comes to clothes. I have no other creative ability, trust me (just ask my hubby 😉) so creating outfits has always been my only outlet.

I am sitting in a window seat and looking outside, as if I am pondering about creating outfits. My hair is in a bun and I am wearing a striped grey and white jumpsuit with a tan robe over top.

Charissa is interested in styling something that she hasn’t worn in a while, something that she has debated getting rid of but hasn’t for fear that steel regret it. To be as helpful as possible, I am going to do the same thing with an item in my “maybe” pile. The maybe pile is a collection of clothes that has been moved to a box in my storage area. For the sake of this post, I am going to be cresting outfits with a jumpsuit that I’m not sure that I want to keep, but like Charissa, am afraid that I’ll regret getting rid of, which is why it’s been living in the maybe pile.

Step 1: What are my favorite attributes of the piece? What makes it stand out?

These are the things that I think about first when I decide to wear a certain thing. For this jumpsuit, I really like the back and I like the waist tie. I definitely want to illuminate these things as much as possible when styling it.

A series of photos that look like they're from a film roll. When I first thought of creating outfits with this jumpsuit, I knew I wanted to show the v back of jumpsuit.

Step 2: What colors work well with it?

In my case, the jumpsuit is made from a grey/cream striped linen, and being neutral, it works with pretty much every color. I am really enjoying the color combo of yellow and grey right now.

I am looking in a. mirror with my hands up to my hair. One of the things that I think about when creating outfits is what colors I can pair together. Here I am wearing a yellow sweater over the jumpsuit and I have tucked the front part of the sweater into the jumpsuit waist tie. I am also wear white high top converse sneakers.

Step 3: Can it be styled for a number of different occasions?

What situations can I wear a certain piece of clothes for? This jumpsuit, in particular, is a pretty casual piece. I tend to think of linen as a pretty casual fabric, especially given how easily it wrinkles. However, the color of this jumpsuit disguises the wrinkles that happen thoughtout the day very well. I think I could even get away with this in a business casual work setting…definitely something that I want to experiment with.

2 photos that look like film roll. The top one is of me in the yellow sweater outfit sitting on a stool with one leg crossed over my other knee and the bottom is a closeup of my leg over my knee.

Step 4: What favorite items do I have in my wardrobe that will work well with it?

It is at this point that I start to look at all of the different ways that I can create outfits with the items that I already own. I look at how different tops and sweaters can be paired with a piece…can they be layered on top, underneath, knotted at the waist, etc. Do I have any dusters or button front dresses that would look good with it?

2 photos of me in the jumpsuit with the tan robe over top, but this time I am standing in front of a white curtain. There is one on top of the other like a film roll. When I'm creating outfits, I like to look make sure that they are comfortable enough to lounge in!

Step 5: What accessories can I add to give it a different vibe?

I admit that I don’t look to accessories much when it comes to styling an outfit. Definitely not as much as I used to. I find that since I have started paying attention to the materials and textures of my clothing, I don’t need as many accessories. But I do like to add a fun pair of earrings or a belt for added definition from time to time. And I love changing up my shoes and purse depending on the outfit, which is why I never add accessories to my capsule wardrobes. I also think that styling my hair differently can give an outfit an entirely different vibe. Well, after writing that, I guess I do rely on accessories more than I thought I did!

Another thing I try to consider when I am creating outfits is the different scenarios that I can style it for. With this one and the following 2 pictures, I have styled the jumpsuit for work. I have tied a black silk shirt over the top of it, buttoned it all the way to the top and added a gold chain and pendant under the collar. I have added white slingback heels and a grey structured bag.
A closeup of the accessories.
I have added a black silk mid thigh blazer to compete the look.

Step 6: Time to try it all on!

After thinking about what colors will work, what occasions I would wear something for, the different items in my wardrobe that I think will look good and the accessories that would bring it all together, I spend a little time playing dressup! I don’t do it as much as I like but I’ll put on a little music (any Joni Mitchell fans out there?), grab a glass of scotch and have a little try on party…usually once the family has all gone to bed! I find that I am much more creative at night and it usually occurs on a whim!

Step 7: Take pictures of the combos that I like so that I have them for future reference.

I like to do this because then I don’t have to think about it again. And this way, I have a record of what outfits I really like that I was able to make with a particular item. I keep them stored in a folder in my photos app to refer back to…and eventually they end up on my instagram account so I can refer back to them there too, at which point they’re a little more put together.

Step 8 [Not really a tip, so we’ll call it a bonus]: Be an outfit repeater!

Once I have an outfit that I really like, I rewear it to my heart’s content! I think it’s important that we all get past the idea that we always need to be doing up with fresh, new outfits or else other people will notice that we’re wearing the same thing. Honestly, nobody notices. and if they Dom who cares! It’s nice to be able to rely on tried and true outfits that you have spent the time putting together that make you feel great!


I hope that this gave you insight into how I go about creating outfits. I hope that you are able to use it to make some new combinations of your own!

See more “how to” styling posts here, here and here.

Now I’d love to hear from you? Do you have a particular process when it comes to creating outfits? Are these tips ones that you would use to put together some new looks? Do you have any tips that you’d like to share?

Until next time,


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An infographic of my 7 step process for creating outfits.
A Pinterest ready image with the title "My 7 Step Process for Creating Outfits" and a flatlay photo of a cream colored sweater under and grey and white striped linen jumpsuit. A pair of clogs is at the bottom of the 2 items.

This Post Has 4 Comments

  1. Olga Gorbacheva

    Thank you for sharing! I have some difficulties with taking pictures, I want them to be, well, not professional, but of a good quality. And I feel that this habit might be very helpful. Also it’s often happens to me, that the same outfit works for a day, and doesn’t for another, and it’s because of weather conditions.

    1. Gillian

      Thanks for your comment, Olga! Coming up with a way to get the pictures that you like can be very challenging. I’m glad that you think some of these tips might help with that!

  2. Lene

    Hi! I found this post so inspiring! It actually made me exited to go through my wardrobe to see if I can make the clothes I don’t wear that often work better for me. My process of getting dressed is very intuitive, so I don’t have any good tips regarding that, but I find it really helpful to write down my outfits in a note book so that I can refer back to them later, sort of an analog version of your picture folder. If I really like an outfit I will highlight it so I can find it quickly in case of an outfit emergency. I also helps me to keep track of which clotes I actually wear.

    It gives me a lot of joy to read your blog posts, and I am so happy every time I see a new one come up!

    1. Gillian

      Thank you so much Lene! I’m glad that you enjoyed it! And I love your system of keeping track of your outfits, especially the part about highlighting your favorites so that you can refer back to them in an emergency!

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