8 Reasons You HATE All Your Clothes…and How To Fix It!

Have you ever opened your closet and thought to yourself, “I hate every single thing I own?” This can happen to all of us sometimes, so we prepared a list of eight reasons why you might be getting this feeling sometimes and how to snap out of it. I never realized how often I was falling victim to number eight.

1. Your Wardrobe is Disorganized

It’s hard to feel excited about your clothing options when you don’t know exactly what your options are. A messy and disorganized closet puts a damper on the entire clothing selection process as you rifle through piles of garments trying to find particular pieces with no clear rhyme or reason to guide you.

You can sometimes feel like you can’t find the items that you’re looking for, and whatever you do find is whatever is close at hand. Oftentimes, that’s whatever is in the front of your closet or perhaps fresh from the laundry. These items are convenient to put on but can make you feel like you’re wearing the same thing over and over again. Talk about being stuck in a rut.

Ultimately, there’s only one way to deal with a messy closet: clean it. Physically, remove all of your garments and accessories and then work on a way to organize them and make them much more accessible for you. That allows you to understand and utilize everything you have at your disposal.

While it is important that your wardrobe should be physically neat, it also needs to be functional, so set aside time to plan the outfits that you would like to wear, audit for items that could benefit your collection, and rotate clothing based on seasonality. This way, whatever is on hand always makes sense. The cleanup will also give you the chance to refresh and renew any items that were trapped in the back of your closet. Give them a wash, a press, or any mending. This way, they’re good as new. Understanding what is in your closet is the first step in understanding how to improve your sartorial collection.

2. Your Clothes Reflect Someone Else’s Style

When confronting your newly cleaned closet, you might ask yourself, “Why on earth did I buy this?” It’s difficult to feel excited about your clothes if you don’t like your clothes. Outside forces massively impact the clothes we buy; social media creates an inaccurate picture of how others look in particular garments, and heavily marketed trends push the illusion of looking perfect for everyone, causing you to buy things you think you need. But the problem is that they’re not actually your style.

Maybe the latest trend doesn’t fit your body well because you don’t have a model’s physique. So, the trendy clothes in your closet aren’t comfortable or maybe the clothes fit but don’t fit your personality, so you wear them in a way that feels awkward and affected. When you’re building confidence and knowledge and how you dress, it’s easy to fall prey to social convention and pressure to wear things that are not your style, but the purpose of dressing well in most situations is to emphasize who you are. So, push through peer pressure and fear of rejection to embrace what you actually like. The final results will always be superior because you feel confident and secure.

First, focus on clothes that generally fit your personal style, then branch out to find new options that fits your base wardrobe. Learn what kind of clothes you really like and orient yourself towards things like that—not trends, fads, or fashion.

3. Your Clothes Don’t Suit Your Body Type

Of course, there’s also the chance that the clothes you find in your closet might suit your tastes but not your physique. Few things make you feel more down on yourself than being confronted with the fact that the clothes you like to wear simply don’t fit well.

This can occur for a variety of reasons. Maybe your particular shape isn’t well suited for the cookie-cutter silhouettes for many off-the-rack clothes, maybe you made these purchases on an impulse or before you understood the basics of a good fit, or perhaps your body has changed since you purchased these items and what once worked for you simply doesn’t work anymore.

Whatever the reason, having a closet full of things you can’t wear will definitely make you hate your options.

Fortunately, there’s a simple solution. First, educate yourself fully on the basics of size, cut, and fit to ensure your clothes look their best on you. We have some upcoming content on this exact topic, which will be released soon. Next, go through your wardrobe and select pieces that can be altered to look good on you. Here, Preston walks you through exactly what an alteration tailor can and cannot do.

Finally, anything that can’t help you look your best doesn’t deserve space in your closet. Having a closet full of aspirational clothes might encourage you to work towards your goal, but it is also more likely to just get you down. So, we think it’s better to get rid of those pieces. You could potentially sell them to finance new acquisitions, but donating is just as good, so long as you’re left with the closet well stocked with clothes that make you look and feel your best.

4. Your Clothes Don’t Have The Quality You Desire

As you’re making your way through your collection, you might start to find that certain garments just aren’t up to your standards anymore, which can make you feel in the dumps about your entire collection.

When you first start building a wardrobe that suits your personality and style, you’re probably not thinking about hallmarks of quality, signs of exceptional craftsmanship, or the importance of durability—and that’s fine. Your goal is to determine what you like and enjoy wearing. But as you gain in know-how, it makes sense to spend more time contemplating good investments and value.

That velvet smoking jacket you wore once to a fraternity mixer worked great when you were in college, but maybe it’s time to upgrade to a mohair dinner jacket.

Once you’re secure in the knowledge of what you like to wear, it makes sense to then focus on quality examples of those items. This way, you can actually enjoy them for years to come. So, intentionally go through your wardrobe and find items of functional quality that might be there and toss anything that no longer passes muster, and for future purchases, focus on the quality over quantity approach.

We prepared several guides on how to identify genuine value and craftsmanship in most menswear items, including suits, shirts, and even ties.

5. Your Selections Aren’t Versatile

An essential aspect of good value is how often you can wear a garment or accessory. Good cost-per-wear means you’re actually getting used out of an item, and when you aren’t able to wear your clothes often because they aren’t versatile, they can fill your entire wardrobe and render it effectively useless.

When you first start building up a clothing collection, you probably aren’t thinking very long-term. You jumped on that orange cardigan because it was perfect for a fall-themed party. But didn’t think about the fact that you don’t regularly attend fall-themed parties. So, when do you plan to wear it next?

Wardrobes assembled haphazardly tend to be filled with both one-off or theme-oriented garments. These are not versatile garments, and they contribute to the feeling that you have nothing to wear. Because poor planning created this problem, good planning is the only way out of it.

Think critically about key items that you’ll need to make your collection more versatile. For instance, for classic style devotees, our essentials include white dress shirts, brown dress shoes with matching belt, navy or charcoal suits, and accessories like neckwear, collar jewelry, pocket squares, boutonniere, and shoelaces. These can help change the look and formality of essential items. This will also help them go further sartorially. Figure out what the essential items for your style of dress are, then learn how to pair them for maximum versatility.

For amazing fragrances and other amazing accessories like the socks and pocket squares I’m wearing today, check out the Fort Belvedere shop.

6. You Have Too Much Stuff

Notice something in common about the previous examples? They all involve having more clothes than you wear. Ironically, one of the ways to feel stuck about your clothing is to have too many options to choose from.

Choice overload makes you feel helpless, almost like there’s no way forward in your style journey. When you have too many clothes to wear, you often default to selecting a few accessible pieces, ignoring the potential for other unique outfit pairings. That’s why cleaning out and culling your wardrobe has been such a persistent theme so far. Doing so allows you to utilize each piece to its best potential, which helps you look your best in turn.

That being said, you shouldn’t feel like you’re only allowed to own two suits and three pairs of shoes, or that everyone has to have a capsule wardrobe. If you’ve seen Raphael’s closet, you’ll know that’s not how he does it. It’s entirely possible to have a lot of stuff without having too much stuff. It’s all about how you interact with your wardrobe and what makes sense for you. Some items definitely deserve a place in your wardrobe. Just take a look at our next example. 

7. You Haven’t Found Your Grail Basics

Like the Holy Grail in Arthurian legend, we found that certain garments or accessories exist that are simply the best addition to any wardrobe. These are often foundational or statement pieces that can enliven an entire outfit. These garments can be perfect for you in terms of fit, material, versatility, and how they reflect your personality.

When your closet is grail-less, it’s easy to feel like something is missing. One of Raphael’s grail garments has been our Fort Belvedere corduroys. They are the ideal weight, cut, and style for him; and in colder months, he wears them all the time and he’s able to build countless outfits from them—suited to many formalities, occasions, and times. That’s because a true grail item will instantly feel like you and make other clothes and accessories instantly feel like you, too, essentially connecting your entire wardrobe with items you often wear.

Put another way, a grail item is that one item you always reach for, that one item that never lets you down.

Naturally, unless you’re Sir Galahad or Indiana Jones, grails are hard to find, but just think intentionally about what your grail item might be based on items you already own and love then, and invest time and effort into tracking them down and acquiring them.

8. You’re Bored With What You Have

If you’ve run through all of these suggestions and you still can’t quite put your finger on why you’re dissatisfied with your wardrobe, it could just be that you’re bored. When all of your clothes feel humdrum, it’s difficult to get inspired and craft really great ensembles.

Does this mean that you have to chuck the lot and buy an entirely new wardrobe? No, but you can get out of the doldrums by treating yourself to one new piece, even if it’s just a small one. 

Take the time to research something that will be fun, versatile, great quality, and timeless. Make sure it’s a great fit for you so you have no regrets when you click buy or take out your wallet. This new addition could add a new perspective to your entire collection and totally transform how you view your closet. And hey, in the worst-case scenario, this new item could be that one thing that you don’t hate in your closet.

Conclusion

As we hope we’ve shown you today, when you feel like you hate everything in your closet, it’s usually because you’re not spending enough time there. You need to be actively aware of what’s in your collection and intentionally interact with your clothes.

To be excited about them, plan your outfits ahead of time, curate your wardrobe, and spend time on maintenance. Things like ironing, washing, mending, etc. When you really get to know your clothes, you’ll find there’s so much to love and nothing to hate.

What tips do you have for fellow classic style gents who feel stuck in a rut with their wardrobe? Let us know in the comments.