We’ve all been there: you spot something on a super-duper sale, you click buy, it arrives, and then it hangs in your closet, untouched. Why? Because when you finally try it on, it triggers an unexpected identity crisis.
For me, it was this Tibi black mini tunic dress. A piece with an elongated collar and sculptural sleeves that I bought because it filled a gap in my closet. But the moment I put it on, I felt a little too sweet, a little too 60s/70s go-go dancer, and frankly, too young (not age-wise, just the overall vibe). My core style words are chill, modern, commanding. The dress was just not commanding enough.
Instead of letting it gather dust or immediately selling it, I decided to run a divergent thinking exercise during this LIVE to truly understand the piece, figure out what was blocking me from wearing it, and break it down through design theory.
If you have a hard-to-style piece sitting in your closet, try breaking down the problem using this framework:
Identify the block: What is keeping you from wearing it? (For me: It felt too sweet and fitted at the waist.)
Identify the appeal: Why did you buy it in the first place? (For me: The gorgeous sculptural sleeves and the elongated collar.)
Find the opposite: If the vibe is too sweet, look for its structural opposites, like masculine, weird, oversized, or even edgy/sexy elements to balance it out.
During the styling session, I tried everything from oversized outerwear to sheer skirts, trousers, and ‘belts’. Here are the winning formulas that transformed the dress from a closet mistake into a staple:
The Oversized Layering formula: To combat the fitted, sweet waistline, throw something oversized and boxy on top. Layering an unstructured white jacket or a dramatic trench over the mini dress instantly modernizes it. You still get the benefit of a short dress, but the volume completely unsweetens the look. Add a pair of contrasting boots or loafers to ground it.
The “Tucked-In” Trouser Trick (my fav!!): Inspired by my recent Balenciaga challenge, I tried tucking the tight dress straight into wide-leg trousers (like my Stellas). By pulling out a bit of extra fabric to create a long torso look, the dress transforms into a sleek, incredibly cool top. It’s surprisingly comfortable, practical for work, and completely reinvents the silhouette.
Sheer Bottom Layering: Since I bought the dress in black partly to layer under sheer skirts, pairing it with a balloon sheer skirt or a contrasting white pencil sheer skirt added instant architectural interest. It turns a risky item into a wearable, textured outfit that feels intentional.
At the end of the day, playing in your closet should be fun. You don’t need to take every experiment too seriously. Some things (like my brief experiment with lavender cowboy boots or the peplum belt ring-dress) won’t work, and that is entirely okay!
The magic happens when you stop looking at an item as a static finished product and start treating it as a design element.
Are you holding onto any hard-to-style pieces in your closet right now? Let me know in the comments below what kind of items you want me to tackle next time!
Okay, that’s a wrap for this one!
If something in here made you nod, send it to the friend who would also nod. That’s genuinely all I want, along with a few more things of course:
🔁 Restack or quote the part that hit, it helps more than you’d think. Especially since I don’t do paid subscriptions, Substack won’t push this one out without your help
💖 Like or comment if you have feelings (I will read every single one!)
🔔 Not subscribed yet? Subscribe, friend!
Find me on Instagram @astahearts for more outfit overthink-ery!
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.