"What matters more than age is how well clothes fit, the quality of the pieces, and how thoughtfully an outfit is put together."

A lot of people assume that as they get older, their wardrobe has to follow a new set of rules (me included). But according to Maddy, that mindset actually makes finding your personal style harder. Because what changes in our 30s and 40s isn’t our ability to wear certain clothes; it's our lifestyle. 

"Someone in their early 20s might be dressing for parties or experimenting with trends, while people later in life could be balancing work, family, and social lives," Maddy said. Naturally, that shift pushes people toward clothes that are reliable, comfortable, and easy to style, without losing their sense of personal identity.

In other words, personal style doesn’t evolve because of new fashion rules. It evolves because your life does.

It's a common mistake for people to build wardrobes around how they wish they dressed instead of how they actually live. 

"Even if I think it looks amazing, I never push someone into wearing something that they don't want to," she said. "I always tell my clients, 'I'm not there to dress you every morning. If you aren't in love with it now, you are never going to pull for it.'"

"What matters more than age is how well clothes fit, the quality of the pieces, and how thoughtfully an outfit is put together," Maddy said. "And paying attention to how garments sit on your body, how fabrics move, and how pieces work together will always be more important than chasing trends."

There are a few different ways fashion experts categorize body shapes. One of the more detailed and sworn-by systems is the Kibbe Body Type System, which looks at bone structure, proportions, and overall lines to help people understand what silhouettes tend to suit them best.

But for beginners (me), I feel like the “fruit” body shape system, which groups bodies into simple shapes based on proportions between your shoulders, waist, and hips, is easier to grasp and a good place to start. 

Here are the six main shapes of the "fruit" body shape system and their characteristics:

– Oval (Apple): broader shoulders and midsection, slimmer legs

– Triangle (Pear): hips wider than shoulders

– Hourglass: shoulders and hips balanced with a defined waist

– Rectangle: shoulders, waist, and hips similar in width

– Inverted Triangle (Diamond): shoulders and hips balanced with a defined waist

– Trapezoid: shoulders, waist, and hips similar in width

The "fruit" body type system is actually considered pretty simplistic, so once you feel comfortable with that, I recommend looking into the Kibbe Body Type System next — this system looks at bone structure, proportions, and overall lines to determine the yin and yang elements of your Kibbe Body Type and what silhouettes suit you best.

And if all the body type categories feel like a lot to remember right now, start with something simpler: the 1:2 proportion rule. Basically, rather than cutting your body visually in half (like with a long t-shirt and jeans), divide your outfit into unequal proportions, like a shorter top with longer pants (1:2) or a longer jacket over a shorter base (2:1). This usually makes a more balanced and visually interesting silhouette.

Her reasoning is actually pretty simple: once you have a few great pairs of trousers or jeans, you can build a huge number of outfits around them.

Think about it this way. if you wear the same pair of jeans one day with a light blue sweater polo and the next day with a white T-shirt, those read as two completely different outfits.

“But if you wear the same light blue sweater polo two days in a row,” Maddy joked, “you’re an outfit repeater.”

In other words, the pants are doing more of the work than you might think.

That’s why Maddy encourages clients to focus on building a small rotation of high-quality bottoms first, whether that’s great denim, well-fitting trousers, go-to skirts, or versatile casual pants that can be dressed up or down.

Once you have this important foundation, the rest of your wardrobe becomes easier (and more fun) to mix and match.

With the right white tee, you can wear it under a jacket, under a button-up/over-shirt, under a sweater, or just as-is and it'll look pull the whole look together.  A structured heavier weight white t-shirt is a solid choice since it holds its own shape and won't cling to your stomach or chest; instead, it creates a clean, architectural line from your shoulders down — this is great for people with a rectangle or oval shape body type in particular. Try on a few different material white shirts and see which you like best.

"And any piece that you are going to wear often should be a piece you choose to invest in," Maddy said.

Ever seen a great outfit and then you look down and he’s wearing some beat up old running shoes? Because Maddy has. I think we all have. 

"You need one pair of shoes for each different occasion — flip flops for the summer, heels for a night out, loafers for a formal event, an everyday sneaker, and a workout sneaker," Maddy said. "Don’t find yourself in a situation where you are wearing running shoes with jeans, I beg!"

This might include quality staples like well-fitting trousers or denim, neutral shirts, jackets, and shoes that can be mixed and matched for different occasions. But when you're dealing with women's fashion, there are so many more options and cuts that it can be overwhelming. 

That's why Maddy G points towards Kendall Jenner as a solid inspiration for starting your capsule wardrobe. "As a stylist, I’m always looking for inspirational dressing, not outfits that only look good because someone is a celebrity or has a perfect body," Maddy said. "Kendall really masters that model-off-duty cool girl vibe in a way that feels achievable and timeless. She isn’t relying on overly sexy pieces or flashy trends. Instead, she leans into high-quality basics, clean silhouettes, and those perfect staple pieces that make up a great wardrobe. It’s the kind of styling philosophy I love: invest in elevated essentials, mix them well, and suddenly getting dressed looks effortless." 

"Her style is proof that great fashion isn’t about doing the most," Maddy said. "It’s about doing the basics really, really well."

Maddy G cites Jacob Elordi as someone who's a great example of a having capsule wardrobe and adding elements to make the outfit fun and trendy. "Have you seen his designer bag collection?!" Maddy continued, "He wears a lot of simplistic pieces and puts them together in a way that is cool and effortless. Of course, being 6’5", handsome, and famous definitely helps, but his style is really easy to emulate, which I love. He’s never wearing pieces that are outrageous or something only a celebrity could pull off."

"So many of my male clients that spend time taking care of their physique want to wear super tight clothing," Maddy said, "And I get it. You work hard on your body and want people to know that. Clothes that fit properly—neither too tight nor too baggy—can look far more stylish than outfits designed simply to show off a physique. A clean silhouette, structured pieces, and thoughtful layering often create a stronger impression than clothing that tries too hard to highlight the body."

A great example of someone who emulates this: NBA player Devin Booker. He's fit for sure, yet he leans towards looser fits. "His style is perfect for the person who wants to pull off a streetwear look but don’t want to look like they are doing It performatively," Maddy said. "Someone that wants to wear some relaxed fit looks, maybe some boxy tees, and some cool sneakers without people thinking they are 'trying too hard.'" 

“Everyone’s body is different, so the odds of buying something off the rack and having it be a perfect fit are pretty low,” she said.

And tailoring doesn’t have to mean completely reconstructing a garment. Sometimes the smallest adjustments make the biggest difference.

“Spend that extra investment to have your pants hit at the proper length,” Maddy said. “It subtly makes a world of a difference.”

Hemming pants, shortening sleeves, bringing in a shirt tighter, or adjusting the waist on a pair of trousers all help clothes sit better on your body, and it can even make something affordable look elevated. So tailor your clothes, especially pieces you know you'll be picking often — it instantly makes an outfit more polished and intentional.

"Having taste does not always mean you have a large budget, and having a large budget does not mean you have style," Maddy said. 

And if you see a piece on a celebrity or out in the wild that you absolutely love, there is almost always either a dupe that's affordable or something close to it that's more in line with your budget. You can reverse Google image search to help you look for alternatives, or you can go thrifting and use the money you saved to tailor the item.

As you get even older, it'll get easier to invest more in the pieces you wear most often, like your go-to handbag, good quality coat, or a suit you swear by.

"It’s all about finding pieces that you feel confident in, that work for your body type, that fit your budget, and that tell the story you are trying to tell."

"Before you speak, before you explain who you are, and before anyone learns about your personality, people notice what you're wearing," Maddy said. "Well-chosen clothing can enhance confidence, attract positive attention, and reinforce the image someone wants to project." 

I started off this article wondering how to dress my age, and now I get that age doesn’t have to limit my or anyone's style. It can actually enhance it. "With more life experience often comes a stronger sense of identity," Maddy said, "and clothing can be a powerful way to express that. And someone in their 40s, 50s, or beyond can still wear modern or trend-inspired pieces; it’s really about adapting them in a way that feels natural and polished."

It turns out, there's a lot of power in an outfit. No wonder Maddy G feels so passionate about fashion. "It becomes a tool for storytelling," Maddy said. "And what story do you want to tell?"