People often ask about my outfit creation process so I have been trying to break it down into a set of useful guidelines. This has actually been quite difficult because I don’t think about outfit creation in a structured way. The whole thing is very intuitive and quite chaotic. But having thought about it for a while I realize that there are definite steps along the way. 

One of the common ways that outfit creation starts is with a single item. Often one of my clients will show me an item they purchased that tickled their fancy, but that they are struggling to incorporate into outfits. So together we get down to business and come up with ways to wear the item to ensure that it deserves a spot in my client’s closet. 

I’m going to use the example of a client that bought the striped seersucker trousers on the right. In less than an hour we went through these steps to arrive at several outfits. 

Assess Fit to Set the Scene

My client tried on the trousers to ensure they fit and looked fab. The fit was similar to that of the model in the picture, except that they were full length with extra leg scrunch. They fit exceptionally well on the bottom, waist, crotch point and thigh, which opened the door to many styling possibilities on top. My client would probably not have been comfortable wearing a tucked top with these trousers had they not fit as well. 

Their tapered hem widths made a range of heel heights a possibility. A wide hem width would have meant committing to a particular heel height in order to sport perfect pants lengths. Their semi-dressy vibe meant that we could dress the look up and down, for work and for play. This information set the outfit creation scene right from the start by influencing the types of items we chose to match with the trousers. 

Keep Troubleshooting Tactics Top of Mind

Throughout the process of combining tops, toppers, footwear and accessories with the trousers, we have three questions top of mind to troubleshoot the combinations that don’t look quite right. 

1. Is it the length of the tops, toppers and trousers causing unflattering proportions? 
2. Is the contrast between the items and between the items and your skin tone too high or too low? 
3. Will the outfit look better with heels? 

I sometimes ensure that we keep these things top of mind by mentioning them to my client at this point in the process. 

Select an Assortment of Tops

The next step is to pull all the tops that might work from my client’s closet and lay them out on the bed with the trousers. As I selected tops from her closet I was thinking about her needs: her comfort zone, how to evolve her look, how to incorporate current trends into the outfits, how the outfit reflects her style descriptor, and the settings in which she’ll be able to wear these outfits.  

Because the blue and white pinstriped trousers are a Summery neutral, we selected tops in neutrals like white, grey and navy, and in colours like green, coral, brown and red. We pulled styles in Summery weights like cotton-rich and silky fabrications, both in knits and wovens, to match the weight of the bottoms. We had an assortment of solids and the odd pattern for a pattern mixed effect. The top silhouettes ranged from formfitting to oversized, long sleeved to sleeveless, blousy to T-shirty, and from high necked to scoop.

As I was pulling out the tops, my client thought some of the tops had great potential, but was unsure about the rest. Perfect! It’s part of my job to gently nudge clients out of their comfort zone by introducing them to new ways of wearing items that might evolve their style. That way their style will feel refreshed, which is part of the reason they asked for my help in the first place. Let the experimentation begin.

Depending on the style of the top, we tried the tops tucked, faux tucked, semi-tucked, and untucked, using the belt that came with the trousers. We scrunched sleeves and added layering camisoles when necessary. With troubleshooting questions top of mind we kept on fiddling with the outfit until the proportions were flattering. 

We scratched the combinations that were “okay”, and stuck with the tops we liked most with the trousers. They covered an assortment of silhouettes, colours, patterns and fabrications because my client had a lot to work with. You might not have as much to work with, which is fine. But you’re good if you have at least three tops that will work with the trousers. 

IMPORTANT: There is no way we would have been able to accurately assess which tops would look best without physically trying them on with the trousers. Looking at the ensemble on the bed is NOT good enough. You must try on the complete combination in front of a full-length mirror to check whether it’s to your satisfaction. 

Introduce the Optional Topper

A topper, either a cardigan or jacket, is not essential to the outfit but a great option in cooler weather or arctic air conditioning. Again, as I went back to the closet to select topper options, I was once again thinking about her needs. She wants to venture into the world of jackets because they look more polished, but she likes the comfort of cardigans and needs more casual options. So out came a cropped navy cardigan, a tailored navy blazer with plaid trim, a blue denim jacket, and a grey blazer with white piping. 

We continued to experiment by throwing the toppers over all the top and trouser combinations. Eventually, all four toppers worked over the trousers with the right top. For example, an untucked and oversized silky navy high-low blouse looked great with an open cropped navy cardigan. A tucked white layering knit top was fab with the dove grey blazer because the white of the top picked up the white piping and buttons of the blazer. The denim jacket looked great over most of the tops, both tucked and untucked. The navy blazer with plaid trim made a delightful preppy and fashion forward statement because it added another pattern into the mix. We scrunched sleeves, turned back cuffs to showcase the striped lining of the grey blazer to add even more pizzazz to the look. We also frequently changed up the outfit by simply swapping out the topper while the rest stayed the same.

I kept on “reaching” for an imaginary light coloured topper in a shade of white to complement some of the outfit combinations. We recognized that this was a wardrobe gap and promptly wrote down the item onto the next shopping list. 

My client then tried on all the toppers with our favourite top and trouser combinations and looked at the outfits in her full-length mirror. Once again, there is no getting around this step.

Ground the Outfit with Footwear

An outfit might not need accessories, but it always needs footwear. The tapered hems of the trousers meant we could match them with any heel height. So we pulled out dressy nude wedged pumps, casual white peep-toe flats, taupe booties, and tan sandals. We made sure that the assortment of footwear could dress the outfit up or down. We paid particular attention to how the colours of the footwear harmonized with my client’s hair and complexion. She has gorgeous brown hair with red tints, so any light or dark brown shade of shoe picked up the colours in her hair and matched the belt, creating instant harmony. Of course, as we applied the troubleshooting questions to the outfit, the light brown and taupe footwear looked particularly fab because it created a low contrast against the pattern of the trousers. 

Further troubleshooting the outfit, we noted that some top and bottom combinations looked better with heels than with flats. For example, longer tops worn untucked over the trousers looked best with the heeled wedges to balance out proportions. Flats and low heels were more elongating when they created a low contrast against the pattern of the trousers. We also frequently changed up the outfit by simply swapping out the footwear while the rest stayed the same.

By the end of this process my client had tried all the footwear options with all the potential outfits and evaluated them in front of her full-length mirror.

Finish off with Accessories

Although I am outlining this process as a set of steps, it is seldom as ordered as this in practice. Although accessories are the last main area to address, in reality we are normally trying them on throughout the process as we get inspired.

My client does not like to swap out her bags so we ensured that all of the outfits worked with her neutral taupe bag. We also kept the belt the same because it was the only one we had to work with. I did suggest a taupe belt and white belt to match the shoes as a way of subtly changing up the look, and adding cohesion to the outfit. The belts were added to the shopping list. 

We wrapped a few scarves over some of the outfit combinations with and without the toppers. In some instances the patterned scarves added extra pizzazz as they picked up the blue/green tones of my client’s eyes. Sometimes the scarves created a fun pattern mixed effect, which was out of my client’s comfort zone. But I suggested that she be a devil and try the look on a day when she’s feeling brave. And often we preferred the outfit without a scarf. 

Evaluating the Outfit Shortlist

I mentioned my client’s needs several times above, and it is worthwhile to revisit those needs one more time with the final set of outfits. In particular, I make a point of thinking about when and where my client will actually be wearing the outfits we have created. After all, there is no sense in creating outfits for an imaginary lifestyle.

For my client above, the versions with the denim jacket were more casual and appropriate for Casual Fridays or casual weekend errands and evenings out. The ones with the navy cardigan were for relaxed non-denim days at the office, while the versions with the tailored blazers were for workdays when extra polish was required.

Then there is the all important happiness factor. Throughout the process we have been thinking analytically about fit and style descriptors and settings and many other factors as we decide which of the flattering combinations are best. But ultimately the thing that makes a good outfit goes beyond that into emotional territory. So during the process, and particularly at the end, I ask my client questions to get at how happy she feels in the outfit. Does it feel a dash fussy and uncomfortable? Do you feel fit and healthy in this outfit? Does it make you feel interesting and attractive? Does it make you feel dumpy and boring?

Of course, sometimes you need to push the boundaries of your comfort zone and violate your happiness factor to experiment with something new. The important thing is that you do this consciously. Let an outfit through if you know how it is testing your comfort zone, but never let one through if there is a nagging doubt that something isn’t quite right.

After we assembled about twenty-five outfits in front of the mirror, it was easy for us to identify the combinations that were the best of the best. So we documented those, as well as the few that were a little outside of my client’s comfort zone, just to have those options too.

Taking it on the Road

You can only take outfit evaluation so far at home in front of a mirror. You need to road test the outfits in motion, in real weather, and in the intended setting. Putting an outfit through its paces is always the best and final way of evaluating it. But being satisfied with what you put together at home has given the outfit a successful start.