As told to Hanna Flanagan, a Cut Shop editor who covers all the best fashion, beauty, and lifestyle products that are actually worth your money. Before joining the Cut, she wrote for Cosmopolitan and People.

Photo-Illustration: by The Cut; Photos: Allison Bornstein, Retailer

Dear Allison,

*I know what I don’t like, but I can’t figure out what I actually do like. I have a hard time styling so many of the pieces in my closet and constantly feel like I have nothing to wear. Should I get rid of these items, or is there a way to make them work? Help! *

*Sincerely, *

*A girl with a closet full of clothes but nothing to wear *

Hi fashion friend,

Have no fear, this issue comes up all the time in my styling sessions. Here’s how I handle it.

The first step is identifying the problem pieces. These are not the things you hate and want to get rid of. Instead, they’re the things you genuinely want to wear but every time you try to style them, you get discouraged and give up. I call these pieces “the hows.”* *

Start by making a pile of clothes you’re not so sure about. Photo: Allison Bornstein

I find most people are really good at identifying what it is about an item that doesn’t work and why it feels tricky, even if they have no idea how to style it. Is it the fit? Is it about proportions? Is it the color? Does it feel too sweet or too hard? Too feminine or too masculine? Is it too western or too boho? Whatever feels off, identify it. That’s really helpful because then we can create a solution.

If a skirt looks very soft and flouncy, you may be inclined to style it with a pretty ballet flat to match the vibe; instead, try the opposite. More often than not, pairing multiple feminine pieces in one outfit will make your look feel very literal and one-note. Swapping the ballet flat for a bitchy pointed pump and adding chunky silver hoops or incorporating some leather is a much better idea; the edge and toughness of those three will offset the femininity of the skirt and balance the look. I’ve talked before in this column about the idea of turning metaphorical dials up or down when it comes to style, and it really applies here — in this example, “turn down” the soft, pretty dial and “turn up” the hard, edgy dial to create harmony.

Tailored trousers and casual sneakers offset the femininity, opulence, and glamour of a vintage fur coat, making it feel more wearable for everyday. Photo: NEREJA

This comes up a lot with vintage pieces. We all love our vintage finds, but if you build an entire wardrobe of items from a specific time period, when styled together, it may read as old lady. People will tell me, “I have this really cool vintage dress, but when I wear it, it’s hard not to make the whole look feel vintage.” Does that mean they actually don’t like the dress and should get rid of it? No. Does that mean it doesn’t align with their personal style? Also no. It just means they need to make sure the other elements of their outfit — shoes, a jacket, jewelry, or something else — feel really modern.

For me, chunky shoes are a big red flag. I’ve owned several pairs over the years, but I never end up wearing them, and every time I clean out my closet, they get edited out. I don’t let myself buy them anymore, no matter how tempted I am by a new launch or how many photos I see of someone styling them well. It may be a color thing for some people; if you’ve always hated green and think it looks bad on you, don’t let yourself purchase an otherwise perfect sweater that unfortunately happens to be green.

Chunky shoes like these have become one of my red-flag items. Photo: Allison Bornstein

So what’s the difference between a “red flag” item and one that’s challenging to style but still worth keeping? The former is a category you’ve tried (and failed) to style several times, whereas the latter is a specific piece. It’s not that I have trouble styling a certain pair of chunky cream ankle boots; it’s that I have trouble styling chunky shoes* in general,* regardless of the silhouette, brand, color, or price point. Next time you clean out your closet, decide what the theme of your giveaway pile is and build your nonnegotiables list from there.

This Colleen Allen coat isn’t something I wear all the time, but when I do wear it, I love it. From left: Photo: RetailerPhoto: Allison Bornstein

This Colleen Allen coat isn’t something I wear all the time, but when I do wear it, I love it. From top: Photo: RetailerPhoto: Allison Bornstein

There are special pieces in my wardrobe that I wear only once a year, but when I see them hanging in my closet, they spark joy. Style is meant to be functional, yes, but you should also have pieces that evoke emotion and feel really special to you. Those that evoke emotion are the ones you genuinely love, no matter how challenging they are to style or how many times you’ve worn them.

‘I Know What Styles I Don’t Like But Not What I Do Like’