Start with the one item you actually wear. Is it trousers with a straight-leg cut? A soft knit sweater? An effortless white shirt? A denim skirt? A simple dress? A jacket you never find difficult to wear? You choose one item you regularly wear and wear easily. This item has already passed the real-life test because you wear it. You don’t have to start from zero to discover what an outfit is all about: you can work with this item.
You hang the item on a hanger or lay it on your bed, or you place it in your lap or on a chair. You look at its color, its fabric, its weight, its cut, its neckline, the position of its waist, its hem length, its overall vibe. A white crisp shirt looks different to a white draped blouse, even if they both are white. Wide trousers alter the silhouette differently to a pair of slim jeans. Because the item’s features determine what you need next in terms of the remaining outfit. If the item is structured, you need some other item that is softer to balance. If the item is loose, you need some other item that is straighter to balance.
You choose one other item that works and test it with the chosen item to make a balanced outfit. If it is trousers, you test two other tops, one or two other bottoms, one or two other dresses; if it is a jacket, you test it with two bottoms and two skirts to find a combination; you observe the proportion before you start testing accessories: do the tops end in a good spot on your waist or hips? Does the trouser break work with your shoes? Does the outfit look boxy everywhere? A tall person will look top heavy. A short person will look bottom heavy? You need help of a full-length mirror or you need a mirror phone app to check the balance as this helps more than looking downwards in the mirror.
You look at color, too. You know your natural color palette even if you have never tried to name it because you have never tried to define it because the one item you wear often already shows you your palette. You test the item once with a neutral and the other time with an accent. Do the colors blend peacefully or are they clashing? You find out if you need a more neutral bottom or top because the color of the outfit is too loud and bright. If the outfit feels too monochromatic and flat, you need to add an accessory, such as a belt, a bag, a scarf or some jewelry. It will make the outfit more interesting without altering it completely.
You notice that the shoes or a layer often make the biggest difference. Your trousers and knit may be casual if combined with trainers, smart if with loafers, and professional if with ankle boots. You may wear your trousers with one coat and one jacket. You will see that a long coat makes the whole outfit look vertical. A cropped jacket changes the waistline position. You may test one outfit with two different pairs of shoes and one coat to see which combination is suitable for the task, the errands, work, study, the dinner, the holiday or the date.
Finally, if the shoes and a layer make a lot of difference, do the accessories, too? If the basic outfit is bright in color, a loud texture or a bold shape, you wear it without too many accessories because your jewelry, belt or bag need to remain more subdued. But if the outfit is a bit dull, it is time to add an accent to make the overall look feel completed. You may test one or two pieces and then remove those that make the outfit look too busy. Some outfits will get better not because you add more but because you remove something.
Now you are in a better position to choose one or two items that fit with your favorite item. If you know how to wear your favorite item, you will also know how to wear an item that matches perfectly.
Keep a style journal of combinations that work. Write down the piece, what you pair with it, how you style the piece, which shoes you wear, what color you pair it with, the overall vibe and mood. You write: “black trousers, cream knit, brown belt, loafers: good for smart casual because it’s balanced at the waist and easy to walk.” You use your style journal to identify your formulas and you do not expect to learn what to wear and what not to in a single session. It takes time. You are learning how to build an outfit with your best piece of clothing so that it teaches you the lesson of proportion, how to choose colors, how to layer, how to make different outfits and combinations.