How To Take Your Wardrobe From Your 20s To Your 30s

“Clothing is a reflection of your current life status,” celebrity stylist Amanda Massi tells Betches

And she’s right. That Forever21 crop top that was a little too tight got you your first free (legal) drink from that finance bro at the bar, and those high-rise skinny jeans? You don’t think you would’ve felt sexy after your last breakup if you didn’t have them. But as the days and eventual years flew by, you reached for both less and less, and eventually they were shoved to the back of your closet where they would never see light again. And if that hasn’t happened yet, it definitely should. 

As your 30s get closer and closer, the person you were in your 20s seems to fade farther away. And trust me, that’s a good thing. The clothes that came with the decade should do the same. 

“Most 20-year-olds are figuring out who they are as an adult, as an individual,  and are exploring different ways to make money,” Massi says. “Clothing really reflects that.”

Personal stylist Samantha Dawn explains that the way you dress in your 20s has a lot to do with the psychological torment you’re going through to try to be liked and accepted. This is why trends — which Dawn calls “terrible” — are a thing

“And then when you approach your 30s, it’s different because you have a better sense of who you are and you’re not trying to fit into a crowd,” she says. “You’re just trying to understand  yourself.”

Your 30s are a whole other identity shift. So how do you make sure your personal style keeps up?

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Image Credit: HBO Max

Dawn’s biggest suggestion is to “dress to express, not impress.” As you’re moving away from a mindset that attaches your actions to the perceptions of others, your wardrobe should do the same. You shouldn’t be dressing for anyone else except yourself. What do you like? What makes you feel cool? 

“Your style is a tool that can be used to attract things that are meant for you: money, connections, places, relationships, opportunities,” she says. This is why it’s so important to make sure your style is authentic to you — so that the eventual opportunities you attract are all in alignment with who you really are. 

So how do you figure out what your authentic style is in the first place? Well, it involves a lot of reflection. Good thing you’re almost 30 and a pro at it.

“Who are you?”, “What is your lifestyle?”, and “How do you want to feel in your clothes” are just some of the questions Dawn asks her clients when they’re trying to nail their personal style, especially during a transitional phase. She then asks them to compare those answers to their current wardrobe. Do the pieces feel aligned with their answers? If not, they’re probably not for them anymore. 

After figuring out how you want to feel, you eventually have to figure out how you want to look. 

And while a certain piece of clothing won’t suddenly make your wardrobe more mature or interesting, over time, you can figure out what works for you and what doesn’t. Massi suggests creating a style or mood board — but not just of things you like. She actually suggests gathering images of things you hate as well. 

“Live in a world of obsessed and absolute ‘I hate this’ and figure out your likes and your dislikes,” she advises. “You’ll see the connecting threads… and even reduce the amount of impulse shopping.”

But she warns to stay away from Pinterest (I know, I’m so sorry) because, as unique as you think your board is, she promises she has seen at least another person have something totally identical. 

Dawn also has some heart-shattering advice: “Stop shopping at the same places — you’re not going to change your style.” So, although you love those Zara tops, it may be time to find a new store. That isn’t to say you can’t hit your favorite shops, but you can’t expect to elevate your wardrobe if you’re still pulling pieces from the same place you shopped at throughout all of your 20s. 

Your 20s are a beautiful, chaotic, ridiculous, and wonderful time. You can honor the life you lived and the person you were — without being stuck in the same jeans. A woman’s 30s mark solidity and confidence. It’s time to make sure your closet is doing a good job of reflecting that. And all that starts with letting go of other people’s expectations for you. Because at the end of the day, all that really matters is that you love what you’re wearing. 

“You wear clothes every single day,” Dawn says. “You might as well choose to put on an outfit that you like.”

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