Ask a Stylist: How to Build a Wardrobe When You Hate Everything You Own

Q: Okay, so I opened my closet this morning and thought... I hate everything in here. What’s wrong with me?

A: Absolutely nothing. Feeling like your wardrobe no longer reflects who you are is super common; especially during life transitions, body changes, or style ruts. Your clothes might still fit, but they no longer fit you. That’s your sign to start fresh, not to spiral.

Q: Where do I even begin? I can’t afford to toss everything and start over.

A: Start with a vibe check, not a shopping spree. Before buying anything new, figure out what you actually like. Save images that make you say, "Ugh, I want to look like that." This could be Pinterest boards, saved TikToks, Instagram folders, or outfits you see in real life.

Then ask yourself:

• What colors keep showing up?

• Are the silhouettes slouchy or structured?

• Do you gravitate toward clean lines or romantic details?

• Are you more tomboy, minimal, French-girl, coquette, or something else entirely?

This is about finding your visual language. Once you know your style vibe, you’ll stop buying random pieces that don’t feel like you.

Q: What if I like a bunch of different aesthetics? My mood changes daily.

A: That’s completely normal. Your style can evolve and be multifaceted. The trick is to build a base wardrobe of versatile pieces, then layer in fun items depending on your vibe that day.

Think of it like a capsule closet with a personality. You can keep things cohesive without feeling boxed in. Neutrals, great denim, solid basics are your foundation. Then mix in statement pieces that reflect your different moods.

Q: Should I do a closet cleanout first? Or will I regret it?

A: Definitely do a cleanout, but be intentional about it.

Try this:

1. Pull everything out and only put back what you’d buy again today.

2. If you're unsure, create a "maybe" pile and revisit it in two weeks.

3. If it’s stained, torn, or doesn’t make you feel good: let it go.

4. If it fits but makes you feel “meh,” also let it go. You deserve better than meh.

Take note of what you’re not wearing and why. That will teach you more about your style than any quiz ever could.

Q: I feel overwhelmed trying to define my style. How do I find a name for it?

A: You don’t need a name, but sometimes labels can help you shop and curate more confidently.

Here are a few examples to try on for size:

• Clean Girl Meets Downtown Cool

• Soft Femme With a Little Spice

• ’90s Minimalist With a Hint of Romantic

• L.A. Vintage But Elevated

You can also look up specific fashion subtypes like “coastal grandmother,” “indie sleaze,” “french minimalist,” or “old money aesthetic.” Even if you don't follow them exactly, they can give you direction.

Q: I keep buying stuff I never wear. How do I stop wasting money?

A: Try this rule: if you wouldn’t wear it three different ways with things you already own, don’t buy it. Period.

Also, stop panic-buying for events. Build a wardrobe that prepares you, so you're not rushing to the mall the night before your friend's birthday dinner. Focus on fit and feel. If something is even slightly itchy or hard to style, you won’t reach for it. Ever.

Q: Do I really need to “invest in basics”? That advice feels boring.

A: Basics are only boring if they’re not your basics. For some, a basic is a crisp white tee. For others, it’s a sheer black mesh top or a silky slip skirt. The point is to build a wardrobe with pieces that go with everything you love.

Your basics should:

• Work for multiple seasons

• Be comfortable and flattering

• Make you feel like yourself, even on low-energy days

Q: How do I make getting dressed fun again?

A: Treat it like play, not pressure.

Try outfit challenges. Lay out clothes the night before. Use an app to track what you wear most. Set a “no black” week or pick a moodboard to recreate. You’re not doing this to impress anyone: you’re dressing to express, experiment, and enjoy yourself.

And remember, you don’t have to have your “signature style” figured out to look and feel good. This is a process, not a test.

Want to Ask a Stylist Directly?

If you’re still staring at your closet wondering what to wear, you don’t have to figure it out alone. On pretties.chat, you can message a real stylist for personalized outfit help, wardrobe tips, or even style therapy. It’s like texting your chic older sister: the one who always knows what looks good and how to make you feel good in it.

Start chatting with a stylist →