things to wear over a dress

HOW TO MANAGE AN OVERFLOWING WARDROBE

Ever found yourself staring at an overflowing closet, thinking, “I have way too many clothes!” but then not knowing where to start? You’re not alone! As a former shopaholic, I completely understand the struggle. At one point, I owned over a hundred pairs of shoes and even converted my spare room into a makeshift closet. I had stacks of clothes I never wore—many still with the tags on!

But now, I’ve shifted to a minimalist wardrobe, and I can confidently say that sometimes less really is more. If you’re feeling overwhelmed by your clothes and want to make a change, here are some tips to help you get started.

How Many Clothes Is Too Many?

As a minimalist, I know many people assume I’d say something like, “You should only own 30 pieces of clothing”—but that couldn’t be further from the truth.

The reality is, there’s no one-size-fits-all answer to “How many clothes are too many?” Everyone’s needs are different, based on lifestyle, environment, values, and priorities.

For instance, as a mom of young, messy kids, I need more clothes on hand for frequent changes and washes. Owning less right now would mean constantly stressing over laundry or running out of clean clothes.

Rewind a few years, though—when I was living solo in a studio apartment with no kids, I needed far fewer clothes. More items would’ve just taken up space, and I could wear things multiple times before washing (no sticky hands or spills in sight!).

The bottom line? What’s enough for you might be too much for someone else, or not enough for another. So don’t stress about finding a magic number. Just focus on what truly serves your lifestyle right now.

Signs You Have Too Many Clothes

A more helpful question to ask is: “Is the cost of keeping all these clothes greater than the value they bring to my life?”

Consider the impact your wardrobe has on you:

  • Does an overflowing closet cause you stress?
  • Do you have trouble finding what you need?
  • Do you feel sad or guilty about items you never wear?
  • Does getting dressed take longer than it should?

If you’re nodding along, these may be signs that it’s time to let go of some items and create a wardrobe that truly supports you.

How To Decide What Clothes to Keep?

So, once you’ve decided to pare down your clothes, how do you choose what to keep?

Start by clearing out the easy stuff: damaged or worn-out pieces. Many areas offer textile recycling options, so consider recycling rather than donating items a thrift store might not be able to use.

Next, focus on identifying your personal style. There’s no need to label it or hunt through Pinterest for ideas. Instead, get curious about what you already own. What do you love wearing? What rarely sees the light of day? Notice patterns in fit, fabric, colors, and shapes. These choices reflect your style—even if it doesn’t fit neatly into a category or trendy term.

Embrace these insights to guide your decisions. Instead of haphazardly tossing items, be intentional about curating a wardrobe that truly resonates with you.

“I Have Too Many Clothes But I Like Them All!”

This is a question I hear a lot—many people struggle with having too many clothes yet feel stuck because they like everything they own.

If that sounds familiar, start by asking yourself an honest question: Are you actually wearing all of your clothes?

If the answer is no, here’s a tough truth: you might not love them all—at least, not on you. It’s a lesson that took me a while to grasp. You can admire a style on others or pin it on Pinterest, but that doesn’t mean it suits you or feels right when you wear it.

Your clothes spending most of their time hidden in the back of your closet is telling. Maybe the fit isn’t flattering, the color doesn’t complement your complexion, or the hemline isn’t comfortable. Deep down, you might already know this, but it can feel easier to say “I love all my clothes” than to admit they don’t work for you or that tastes and needs have shifted. Facing these truths is the first step toward letting go.

But what if you do love and wear everything?

In that case, consider why you want to downsize. Are you short on closet space? Feeling overwhelmed by too many options? Pinpointing your motivation will help guide your decisions.

Then, compare the satisfaction of achieving these goals with the discomfort of parting with a few special pieces. While it’s not always easy, sometimes letting go of a few items can help you create the space, simplicity, and joy you’re truly after.

“I Keep Buying Too Many Clothes…”

Decluttering is a great first step, but the real solution is to manage what’s coming in. If shopping is part of the issue, then focusing on your buying habits can make a lasting difference.

If this resonates, here are some blog posts that might help:

  • 4 Reasons Why You Can’t Stop Shopping + What To Do About It — Do you find yourself always buying new clothes or unable to resist a deal? This post dives into the reasons behind impulsive shopping and offers tips for changing your habits.
  • How to Stop Online Shopping (Tips From a Former Shopaholic) — Is your closet overflowing because of online shopping? Check out this post before clicking “add to cart” again.
  • How to Stop Buying Clothes You Never Wear — The average person wears only 20% of their closet. If you’ve got plenty of unworn items, this post offers strategies to break the cycle.
  • 7 Signs You Have a Shopping Problem + What To Do About It — Frequent buyer’s remorse is just one sign of a shopping habit. Read about six more signs and actionable steps to take control.

Other Ways to Reduce Your Number of Clothes

Decluttering is a fantastic way to make space in your closet, but you can also ease into owning fewer clothes and simplifying your wardrobe with a few fun approaches:

  • Project 333 — This minimalist fashion experiment involves dressing with 33 items for 3 months. It’s a great way to “test drive” a pared-down wardrobe without committing to a full overhaul.
  • Try a Minimalist Capsule Wardrobe — Instead of simply decluttering, create a capsule wardrobe, a streamlined collection of items that mix and match easily. This step-by-step guide helps you build a versatile wardrobe you’ll love.
  • Experiment with a Personal Uniform — If you’re overwhelmed by choices, a personal uniform can simplify getting dressed. For anyone who feels pressured to constantly change outfits, this approach can bring ease and consistency.

Do you feel like you have too many clothes? What’s the hardest part about letting go?

conclusion

In the end, simplifying your wardrobe is about finding what works best for you. Decluttering, experimenting with capsule wardrobes, or trying a minimalist project can all help you build a collection of clothing that truly adds value to your life. Remember, there’s no “one-size-fits-all” approach—just a journey to creating a wardrobe that reflects your style, supports your lifestyle, and brings you joy without overwhelming you. Embrace the process, and you’ll find yourself with a closet that feels lighter, more intentional, and easier to manage.

7 ESSENTIAL STYLE TIPS FOR MEN OVER 50 BEFORE YOU SHOP

Navigating the world of fashion in your 50s (and beyond!) may seem daunting, but trust me, it’s entirely achievable. While I can’t personally guide every man receiving an AARP membership in the mail, I can offer you this comprehensive guide to dressing for mature men.

If you’re new to my writing, you might be asking yourself: Caroline, as a 29-year-old woman who spends her free time watching Nordic crime dramas and perfecting my homemade macaroni and cheese, what do I know about the style dilemmas faced by men approaching early retirement?

Well, for one, I have a soft spot for well-dressed older gentlemen.

Every man over 50 has unique wardrobe needs that reflect his personal style and lifestyle. Whether you’re searching for casual attire, looking for shopping recommendations, or simply wanting to elevate your fashion game, dressing well at this age can be just as exciting and diverse as it is for younger men.

Not sure where to begin? No need to fret! Below, 7 tips on nailing mature style for men:

Get a tailor

Everyone I’ve spoken with in the realm of men’s style, especially for those over 50, agrees on one crucial point: the difference between “a guy wearing clothes” and “a well-dressed man” often comes down to good tailoring.

Building a relationship with a tailor is essential for any mature man looking to elevate his style.

Consider your tailor your clothing’s doctor. Just as you have a dentist for your teeth, an internist for your health, and a dermatologist for those pesky moles, it’s time to have a tailor on speed dial to ensure your wardrobe is in top shape.

Now, I can already hear you thinking: “The clothes I own fit me just fine!”

But let’s be real—no man, and I mean none of you, can wear off-the-rack clothing perfectly.

Sure, you don’t need to have every t-shirt tailored or sweatpants hemmed, but those button-down shirts you wear daily with jeans or chinos? Get the sleeves adjusted to the right length.

And don’t forget about those jeans and chinos! 

What about the blazer you wear for dinner with your spouse each week? Could it use a little adjustment to fit you better?

Think of this process like visiting a doctor. You don’t go in every day for every little issue, but for the significant matters, you want to consult a professional. 

Focus on the finishing touches 

When it comes to presentation, the key differentiator between well-dressed men and those who simply wear clothes is the extra attention to detail. These subtle touches may not be immediately noticeable, but once you see them, they make a significant difference.

This attention to detail extends beyond your clothing to grooming, including a well-maintained beard (and nose hairs!), clean nails and cuticles, and a pleasant scent. Just look at the smart tie and coordinating socks worn by Stanley Tucci—voted the most stylish man of 2023 by Style Girlfriend followers!

Accessories are an excellent way to elevate your style as a man over 50. A beautiful scarf can enhance a simple blue overcoat, while the right shoes can complete your outfit—just as easily as the wrong ones can ruin it.

Investing in accessories is a smart choice for your wardrobe. Timeless pieces, like a classic pair of glasses, will never go out of style, and if you choose quality items built to last, you’ll enjoy them for years to come.

I’d like to highlight timepieces: they’re one of the first things I notice on a man. If you wear a watch, I can’t help but notice which one it is.

Let me be clear: you don’t need to spend a fortune on a watch. However, if you can invest in a quality timepiece, it’s often worth it. Even an affordable tank-style Seiko can make you look polished and distinguished.

Invest in forever pieces

By avoiding fleeting trends, you can invest more wisely in your wardrobe. Why? Because when you focus on timeless pieces, you know you’ll wear them for more than just one season.

Instead of purchasing multiple inexpensive shirts and trousers, consider buying one or two high-quality staple items. Then, invest in having those pieces tailored to fit you perfectly. The final step? Embrace the ease and simplicity of cultivating a signature personal style!

Look for brands that prioritize craftsmanship and quality. 

While you may not have the budget to splurge on every item in your closet, you can be strategic about your spending.

Identify the pieces you wear most frequently. If you rarely wear sweaters but often don blazers—think of a post-presidential Barack Obama—prioritize your budget accordingly to reflect your lifestyle.

Lean into a Monochromatic Color Palette

Monochromatic dressing involves combining pieces from the same color family to create a cohesive and polished look. This style not only elongates your body but also gives you a sleek, modern appearance with minimal effort.

Take, for example, the character Steve Martin, 79, plays on Only Murders in the Building. He often sports monochromatic ensembles, like blue jeans paired with a white shirt and a blue knit sweater or overcoat.

For men over 50, these outfits are not only simple to assemble but also effortlessly elevate your style.

You can approach monochromatic dressing in a few different ways. Our favorite at Team SG is the black and blue route—opting for rich, deep blues like navy—or embracing earth tones, such as pairing tan chinos with a chunky oatmeal rollneck sweater.

Aim for leveling up your personal style instead of chasing trends

Here’s a little secret: I often share this advice with my younger clients, but it’s especially true for older gentlemen—dressing for who you are, rather than trying to keep up with the latest trends, makes all the difference.

By midlife, you’ve witnessed countless trends come and go, which makes it easier to identify which cuts and styles flatter you and which colors and textures enhance your personal aesthetic.

Consider what clothing aligns with your lifestyle and which pieces don’t quite fit who you are. 

Think of this guideline not as a limitation, but as a permission slip to bypass fleeting trends. That’s a true luxury! As men age, they naturally become more distinguished—there’s a reason the term “silver fox” is a compliment.

Allyson B. Fanger, the costume designer for Netflix’s (criminally underrated, in my opinion) *Grace and Frankie*, shared that one of the joys of dressing older characters like Robert and Sol—played by Martin Sheen and Sam Waterston, both in their eighties—is that these men have lived rich lives.

The show features two lawyers who leave their wives for each other after their kids have grown up, and their style is spot on.

Robert and Sol don’t need to evolve further in their fashion choices, which makes dressing them all the more enjoyable for Fanger.

They each have favorite brands, signature color palettes, and distinct approaches to style.

Robert is traditional, favoring button-down shirts and chinos—he’s a Brooks Brothers man through and through.

Sol, on the other hand, embodies the spirit of a hippie, opting for Cubavera camp shirts and comfortable Tommy Bahama linen pants.

These characters exemplify how, regardless of personal taste or style, it’s entirely possible to achieve top-notch personal fashion at any age.

Ultimately, knowing who you are and being confident in that is the cornerstone of any man’s style, and that understanding becomes more profound as you accumulate life experience.

Adopt a wardrobe uniform

Larry David, at 76, is a big advocate for uniform dressing. While many people think of a daily uniform as a traditional suit and tie, David exemplifies how versatile and liberating this approach can be.

He’s a king of casual style—if you’re searching for casual clothing ideas for men over 50, the *Curb Your Enthusiasm* star offers an excellent blueprint.

His go-to wardrobe staples include crewneck sweaters, zip-ups, AG 5-pocket chinos, and soft shoulder blazers. 

If the thought of choosing an outfit every day feels overwhelming, this dressing strategy might be perfect for you. 

Consider building a capsule wardrobe filled with a few pieces you love: your favorite pants, a handful of shirts that make you feel your best, and some knitwear or jackets.

And don’t hesitate to buy items you adore in multiple colors! (This is another trick David uses.)

This way, each morning, you can reach into your closet and confidently know that whatever you pick will likely coordinate beautifully.

Be yourself 

It might sound a bit silly to wrap up a list of style tips with a reminder to just accept yourself, but hear me out. You might think, “My style is just a ripped sports jersey and Crocs,” and to that, I say: maybe it’s time for a change! (Just kidding… or am I?)

What I really mean is don’t overthink dressing for a particular age. These style tips are helpful if you’re unsure where to start or want to elevate your look. But if you already have a signature style or enjoy dressing outside the norm, don’t let the number in front of your age hold you back. Embrace what makes you unique and wear it with confidence!

CONCLUSION

In conclusion, navigating style in your 50s and beyond doesn’t have to be a daunting task. Embrace the principles of good tailoring, invest in timeless pieces, and build a wardrobe that reflects who you are. Remember, personal style is all about confidence and authenticity—wear what makes you feel good, whether it’s a classic blazer or a funky shirt.

Don’t shy away from experimenting with accessories and details that can elevate your look. And most importantly, don’t let age define your fashion choices. Celebrate your individuality and express yourself through your clothing. After all, style is a lifelong journey, and it’s never too late to redefine your aesthetic!