Changing your style can be hard.
You’ve dressed a certain way for a large part of your life, and it feels like it’s part of who you are. Changing it can feel like you’re changing your identity.
You know you want to step up your style. You may even have a specific look in mind that you want to adopt.
But when you’re in the store, and you try on something new, it just doesn’t feel right. It doesn’t feel like you.
You worry that it’s just not your style. You worry that you don’t know how to pull it off. Or you worry that your friends, brothers or colleagues will react negatively to the new you.
And at that moment, you forget how much you desire a style change. You forget the look you have in mind. You convince yourself it just isn’t you.
But the truth is: It’s just not you yet. That doesn’t mean it can’t become you.
A new look always feels awkward at first, because change in general feels awkward, especially when you’re changing something about yourself. I mean, I feel awkward every time I get a freaking haircut.
But that doesn’t mean we should avoid change altogether. Changing your style is worth it because you step closer to the man you want to be.
And changing your style doesn’t even have to be that hard. You have plenty of ways to ease into it.
Why Changing Your Style Feels Awkward
Many guys assume that changing their style can only happen one way — drastically.
They think the only way to change is to instantly move from hoodies and jeans to sport coats and slacks.
But small steps can also accomplish lasting change. In fact, taking small steps has a much higher success rate.
Because by taking small steps, you circumvent all the worry that accompanies a big change. By taking small steps, you avoid shocking the people you know, and they’ll be more open to accepting the new you without ridicule.
Small steps feel more comfortable too, because you stay close to the look you and the people around you are already familiar with, while you gradually step it up.
So how do you take small steps toward changing your style?
1. Start With What You Know
Instead of changing your look, you could first try improving the look you already have.
So instead of trying new things, you look for better versions of clothes you already wear.
That means if you’re used to wearing faded jeans, you can start by getting a nicer pair of jeans, or a T-
These are small steps, but they can substantially improve your overall look. And even though you’re not making drastic changes, you are learning and improving.
2. Upgrade Smoothly
Start upgrading to the look you want by using the upgrading technique.
The upgrading technique works by taking the clothes you already have in your wardrobe, and thinking of alternatives that are slightly more in the direction you want to go.
So if you want to move from sneakers to dressier shoes, you could upgrade with the following progression:
- Desert Boots
Or if you want to move from graphic tees to dress
- Graphic tees
- Solid tees
Or, lastly, if you want to move from hoodies to blazers, you could upgrade with the following progression:
- Zip-up cardigans
- Button cardigans
See? This way you don’t have to change in one go, but you start with clothes that are closer to what you’re familiar with.
3. Wear Transitional Outfits
You don’t even have to upgrade your whole outfit at once. You can ease into wearing your new clothes by using transitional outfits.
Essentially, this means you just wear your new clothes mixed with your old clothes.
So let’s say you start with the following look:
- Faded jeans
- Graphic Tee
And the next stage would be this look:
- Dark denim jeans
- Solid tee
- Zip-up cardigan
Then, you can try these transitional outfits:
- Faded jeans, graphic tee, zip-up cardigan
- Faded jeans, solid tee, hoodie
- Dark denim jeans, graphic tee, zip-up cardigan
By wearing your new clothes with your old clothes, you’re not changing your look that much. You’re only changing one or two items, which will look and feel much less drastic.
Check out the image below to see examples of transitional outfits between the two looks described above. (First look is top left, and second look is bottom right.)
4. Use “Gateway Clothes”
Many people say you should invest more money in clothes to get higher quality. Because higher-quality clothes not only look better, but they also last longer. So in the end, you actually save money.
But for a beginner who’s still experimenting and trying to find a look that works for him, that’s terrible advice.
Because when you’re trying something new, and it comes with a hefty price tag, those worries that it might not be right for you will hit you twice as hard. Especially if you’re on a budget.
And you’d be right, because you’re still in your experimental phase. You don’t know for sure that something will work for you. And you might find that you liked the idea of it more than actually wearing it.
You might find you don’t like wearing it at all.
So you use gateway clothes, which are affordable clothes that you use to experiment. You use them to get a feel for the style you’re after. And you use them to discover what works and what doesn’t.
And once you figure all that out, you can consider higher quality. Because then, you’ll know better what you’re looking for.
You won’t worry as much whether something is right for you, because you already tried it, and you’ll have the confidence to spend a bit more.
5. Avoid Bold Fashion Statements
Some guys who want to dress better struggle with the idea of people noticing. They’re afraid how people they know might react.
If that’s you, then you don’t want to call too much attention to you trying new things.
Instead, when you try something new, keep it relatively simple and understated.
Avoid anything that’s too bold, too trendy or too out-of-the-ordinary.
So if you’ve never worn a blazer in your life, go for a simple one in navy or grey, rather than a bold red number.
The fact that you’re trying something new is bold enough, for now. Going for more attention-grabbing pieces will only make you feel more awkward.
Add some bolder clothes once you’re comfortable enough to sport your new look with confidence.
Step Up Your Style One Step at a Time
Changing your style doesn’t have to be hard.
It only seems hard, because you’re picturing a drastic departure from the look you’re familiar with. But your style change doesn’t need to be drastic. It can be gradual.
And gradual change actually has a higher chance of lasting.
Because the more awkward you feel sporting a new look, the more likely you’ll give it up and mark it down as something that just wasn’t right for you.
But if you take small steps toward the look you want, you won’t feel as awkward. You gradually get familiar with stepping closer and closer, until you reach the look you want.
And if you think all this will take too long, isn’t it better to change slowly and succeed than to change quickly and fail?
Besides, taking small steps will give you more confidence to take bigger steps. And before you know it, you’ll walk down the street looking like a new and improved man.
You’ll look like the kind of man you truly want to be.
And you won’t just look damn good — you’ll feel damn good.
What’s your approach?
Are you more of an “all-in” type guy who dives head-first into style changes? Or do you prefer the methods I suggest here?
Would love to hear your thoughts in the comments below.