Your styling process might benefit from starting with one item that you already feel good in, that is, a piece that fits and feels “easy.” This could be a pair of straight-leg jeans or a pair of trousers, a sweater in a neutral, a denim skirt, a white shirt, or a jacket that tends to pull you together. For the purposes of styling, call the chosen piece the anchor item. The anchor item anchors the outfit, meaning it gives you a place to start rather than leaving you in the center of the wardrobe, thinking, What’s my color? Silhouette? Fabric texture? Shoes? Accessories?
There is nothing wrong with an outfit with a strong statement piece or a very cool jacket as an anchor. However, often a less “exciting” item is better to anchor the outfit, because it gives you more clarity regarding the rest of what you’re wearing. Select something that fits, has practical relevance to your life right now, and can link to multiple other items. If it’s just something that works with one specific item, maybe it’s not a great piece to start with. A good anchor item gives you some room to play with layering, contrast, and weight of the fabric, scale of accessories, etc.
Once you have selected your anchor item, add one item to pair with it and consider how they go together as a duo. If your anchor is dark trousers, try the outfit with a light top, then notice the contrast between what’s on top and bottom. Or, try a skirt with a print with a light neutral piece, and see how it feels with that. If your jacket is oversized, see if you need accessories before you put it on. It’s easy to get caught up in the idea that more is more, so adding more pieces to get that look, but often the simplest pairing is actually what creates the balance (and confusion) we feel at the end.
Then look at shoes because it can really shift the proportions. The same straight leg jeans can appear with a flatter shoe like a flat, but sharper in a loafer; heavier boots. The same dress or skirt can be casual but not really ready for the evening or just look really awkward in a specific shoe. Look in the mirror at the full length of the outfit, from neck line to waist line to hemline. You aren’t trying to find the right thing, you’re looking for the thing that helps you to understand what each item does.
Consider three versions of the same outfit with the same anchor but a few different pieces added (the layer, the shoes, the accessory). Try taking photos because they usually show the silhouette better than your quick glance. Does one version feel too “flat,” or is the color palette too similar? Is one too busy, with both a statement piece and an accessory? Is there one that feels cleaner once you take a piece away? It can be helpful to jot a few notes after you wear the piece, because you’ll likely try to remember all the details the same way. Note what your anchor was, and what you thought worked, and what didn’t work. Maybe the colors were good, but not the weight of the fabric. Maybe it looked good in the mirror, but it was a bit uncomfortable. Maybe the shoes did a great job shifting the proportion, but didn’t fit the “event.” It helps to start building these styling notes to turn one outfit into your personal style formula.
There’s no doubt that building an outfit in this way takes a bit of pressure off; there’s less of it all to consider. It changes the question from “What is my style?” to, “What supports the anchor today?” The latter is an easier one to answer. You will soon begin to notice what anchors in your wardrobe work better with others, which feel natural and “right,” and which help make everything else make sense. That’s where the magic happens: where the styling feels more like observation than guessing.