"I'm Looking For Ways To Dress Better Today, Where Do I Start?"
(photo: Courtesy of Mr. Jonathan Daniel Pryce, Garçon Jon)
Most men ready to level up their appearance have asked themselves (or others, in this case) this question. I get it. (Re)discovering your personal style may be daunting. And while you might think so, it's NOT because you haven't been keeping up with the latest trends. Or weren't born with 'an eye for good style.' (trust me: no one is)
Here's the thing: when you've been prioritizing other things over your appearance because they deserved your undivided attention, it's normal that 'good enough' clothes became the norm. But that doesn't mean you should continue to settle for less while you've been achieving more. You know that this can cost you. In your performance, but more importantly, in empowering and portraying your personal brand. Good enough isn't good enough. We both know you deserve nothing less than the best.
13 Possible Reasons You're Not Dressing Your Best (Yet)
I understand we all get stuck in our ways. We make subconscious decisions, maybe even conscious ones, because we lack a better solution. So let this be your fresh perspective to help you crack the code of why dressing like your authentic self might not fully happen for you right now—and what you can do about it so you can finally start feeling good in the clothes you wear.
1: You give your partner complete control
It's great to have someone looking out for your style. But your style is about you and not about the people around you. Guidance and opinions are welcome, of course. Especially if your partner is an expert, keep in mind that developing your own 'eye' will serve you in the long run. And to be fair, aren't we all a bit biased? It's always easier to recommend something from your own point of view and personal preference – so they will, even if they try not to. Keep that in mind.
2: You are waiting for the right time, feeling, moment, or body
Are you the type of man who limits himself by believing you have to be confident, have a specific body type, or focus on others first before you are "allowed" to dress well? Well, I've got some news. Multiple studies have proven that ill-fitting clothing makes us feel uncomfortable and self-conscious. Wearing clothes that fit well and flatter your body, on the other hand, enhances your self-esteem and boosts confidence.
3: You assume you know your size ("I'm always a Large")
No outfit is a good outfit if the fit and size are off. So, don't simply buy what you think your size is. Make sure you know your actual size. You might want to get measured by a tailor if you plan on maintaining your physical shape or seeking made-to-measure looks. But a good hack I personally love is always taking multiple sizes with you in the dressing room: what you think your size is, one up and one down.
4: You're skipping the shoes
The details of your look are as important as your actual clothes. Yes, it's one of the first things people notice and might even judge you. So, don't forget about the shoes when you've treated yourself to a good outfit. This doesn't always mean you need to buy a new pair. Simply make sure they look presentable and are clean. (PS: running shoes aren't day-to-day footwear).
5: You assume expensive equals better
As you notice from this list, assuming is never a good idea. More expensive doesn't always mean better quality garments. The key to great style is investing in the right pieces you can work with for a longer period of time. These pieces help create Style Overlap in your wardrobe and together make up your version of the perfect minimalist wardrobe. So it's essential to know the difference between what's better and what's just a higher price point.
6: You're big on buying without consideration
Always think of possible combinations when you're eyeing an item before swiping your credit card. A good rule of thumb is to picture at least five ways to wear this new item using your current wardrobe.
7: You hide behind the limiting belief that dressing well is only for some
Looking stylish and showing up well-dressed daily isn't only for certain people who have developed an 'eye' for style and fashion. I want you to know that dressing well is a skill everyone can develop through practice. Everyone started at zero, even if they don't look like that.
8: You're copying others 1:1 and hope for the best
It's great to get inspired by those around you and people online. Duplicating the exact looks of others, not so much. If this is your current strategy, developing your own 'eye' or personal style can get quite tricky. These outfits look good on them because it's their personal style, which they put a lot of thought into. Ask yourself what you like so much about this current look (certain items/colors/style) or is it more the feeling the person seems to convey?
9: You're rushing into things
It takes time to develop that unique 'eye' and, thus, an idea of what works best for you. Allow yourself the time. And have fun while you're at it! I know you aren't big on spending hours in poorly lit dressing rooms with a sales advisor who bothers you a bit too often (and simply tells you everything you're trying looks good). Luckily, there's so much you can do before getting to this stage—such as gathering inspiration, discovering your perfect fits, and getting a quick run-down on your current wardrobe—so you'll go out shopping well-informed.
10: You have no idea what you love about your current wardrobe
If you're in for a style transformation, you might want to skip out on all you currently own because it "just sucks." No matter how you feel about the pieces that make up your closet, they hold a lot of useful facts about you and your personal style moving forward. No worries, closet edits don't need to take long. Simply try spotting any buying patterns, materials you love, colors you're clearly drawn to or are missing, etc. So you'll know what (not) to look for.
11: You limit yourself into thinking you can't pull things off
"Bad buys" aren't always bad buys. Unless the fit, size, or color is extremely off, there's a reason you bought it. Try putting yourself back in your shoes when you were purchasing it, what you were picturing combining it with, and maybe even what you were wearing at that moment (and the mood you were in).
💡 Or ask me for help! I'm just a call away and would gladly help provide a fresh styling lens.
12: You easily fall for the next big thing, trend, and hype
If you've got a fair budget to rebuild your style and wardrobe, that's great. However, if you don't know how to spend it and you end up with too many bad buys.. (and a fast-emptying wallet), here's my advice. Find out who the true specialists are for the things you are eying or love wearing and are worth the investment (even if you can't afford them just yet).
Saving up for a beautiful, top-of-the-bill piece and working towards it will help you become a more considerate buyer. Once you do, you'll also appreciate what you have more. You'll want to wear it more often and will naturally seek more ways to create outfits with this piece.
And the best thing? Sometimes, along the way, you'll find out that you don't truly need all the things. It might take longer to gather the clothes you need, but it's for a good cause: a wardrobe full of high-quality pieces you love.
13: You would rather underdress than overdress
I get it. You'd rather not get the dress code wrong. But get this: it's always better to have made a bit too much of an effort, even if I feel that doesn't exist. Expressing and embodying your redefined personal style sometimes feels like overdressing, but I have never heard of anyone who's been approached negatively about it. Plus, I'd always choose to be the James Bond over the Adam Sandler. What about you?
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