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.

Five Easy Ways to Smoothly Step Up Your Style

Changing your style doesn’t have to be instantaneous. You can take some time and ease yourself into it.

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-shirt that doesn’t look like it’s twice your size. If you’re used to wearing hoodies, try finding some that are more form-fitting.

hoodie upgrade

A small step, but it’s in the right direction

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:

  1. Sneakers
  2. Desert Boots
  3. Loafers
  4. Brogues

Or if you want to move from graphic tees to dress shirts, you could upgrade with the following progression:

  1. Graphic tees
  2. Solid tees
  3. Polo shirts
  4. Casual shirts
  5. Dress shirts

Or, lastly, if you want to move from hoodies to blazers, you could upgrade with the following progression:

  1. Hoodies
  2. Zip-up cardigans
  3. Button cardigans
  4. Blazers

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.

hoodie to blazer

Going from a hoodie to a blazer is a big step…

3 upgrades from hoodie to blazer

…But with a few small steps in between, the upgrade looks and feels more natural

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
  • Hoodie

And the next stage would be this look:

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.)

transitional outfits

By taking small steps and gradually changing your style, people will barely notice you’re doing anything different.

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.

low-key and bold blazer

When trying something new, avoid bold statements (right) and keep it low-key (left) [image source]

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.

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19 Responses

  1. Sirilly on

    Being the eager and passionate person I am, I happened to change my style very quickly. And I failed A LOT lol, but ultimately I have become a better dresser. So I’m happy. I’ve always implemented the gateway garment advice though, because there’s always something new you’ll want to try when finding your personal style. I feel as if I am just entering a more intermediate level of things now, but I’d to like to thank you guys for helping me out in my earlier days. Without the articles on RYS, and books like the Lean Wardrobe, Dressing LIke a Grownup, and The Effortless Guide to Graduating Your Style. I don’t know where I would be. So thanks again guys for continuing to help gents like myself grow everyday. It’s awesome.

  2. Joshua on

    All in.

    Started with frayed jeans and a tee. Less than year later, all I wear pretty much everyday is odd dress pants, dress shirt, dress shoes, and a sport coat. Though you could say I had transitional phase when I had only one sport coat and the rest were being made.

    • Robert van Tongeren on

      That’s awesome, Josh. The ability to dive headfirst into unfamiliar waters isn’t something all guys have. You should be happy you do.

      I should note though, the above methods won’t necessarily take guys much longer. Rather, they allow them to set their own pace. Getting from A to B within a year is entirely possible (and even, probable) within a year, even if you’re taking small steps.

  3. Joe on

    I don’t know if i’m the exception but my transition was from graphic tees and blue jeans to ocbds and chinos/ darker jeans to sweatshirts/henleys and chinos/jeans lol

    • Barron on

      Do you wear one outfit or another based on the degree of casualness of where you’re headed? Henleys and sweatshirts have their place just as OCBDs have theirs. Just depends on what you’re doing and where you’re going.

    • Robert van Tongeren on

      Most guys struggle more with dressing up rather than dressing down, which is why I chose that as an example. It’s not the only kind of transition you can make.

      You could use the same techniques to go from conservative to rock&roll, if that’s what you want. Or from formal to more casual. It depends on the kind of look you want for yourself. It depends on how you want people to see you.

      And like Barron said, you can switch around for different occasions.

  4. Marc on

    I’m still trying to transition to wearing a sportcoat or blazer consistently to work or out on the town. I did get some use during the holidays for parties, and obviously get some use for special occasions, but haven’t been able to stick with it. I’m currently at odd trousers and either a button up cardigan or v-neck sweater. I guess my main mental hurdle left is the fact that I’d be the only person at work other than the sales department manager wearing one. I appreciate the classic and masculine look, but don’t want to have to explain myself for dressing so well in a jean/casual shirt environment. Any advice other than simply “man up and do it”?

    • zachary on

      if you sit at a desk on a computer you probably wouldn’t want to wear the blazer at that time anyways (at least I don’t like to), so maybe wear it in but hang it up for most of the time you’re in the office? Wearing it during your commute, out of office meetings, happy hours or other after work events should feel pretty good.

      • Marc on

        Thanks Robert, Barron, and Zachary. I’ll start easing into it and as Zachary pointed out, ensure I don’t kill my blazers while desk jockeying.

    • Barron on

      Ease into it, as far as frequency. Do it once a week for a month, then twice a week the following month, or whatever frequency with which you’re most comfortable. The more you wear it, the more easily digestible it will be for those around you. If people question you, simply say you like wearing it, or you feel good in it. After all, that’s the truth, right?

    • Robert van Tongeren on

      See below.

      And just to add, don’t be afraid to be the only person wearing something, if you like wearing it. You might get some comments or quips at first, but if you don’t make a big deal out of it, they won’t either.

  5. zachary on

    Great topic – it isn’t talked about enough. I am almost over the hump on this (gradual) transition myself, and the only advice I’d really offer to anyone starting is to find a good tailor and completely trust them. Any time I’ve tried to impose my opinions on size or proportion, I just made it worse and had to redo afterwards. I’ve learned not to try to micromanage a tailor at least while in transition, when your head is not so clear!

    • Barron on

      Yep, good point. There will come a time when you know exactly what you want and how you want it done, and if a tailor is telling you otherwise at that point, you should assert yourself. However, in the beginning, if the tailor is good, you should trust his suggestion.

    • Robert van Tongeren on

      Good to hear you’re almost over the hump, Zachary. And I agree, tailors tend to know best. (Though, when I first started visiting tailors, I didn’t even have much opinions to impose on him, anyway :p)

  6. nancygoldblatt on

    Robert, Nice article. We all need to feel safe. If we make changes that don’t push us too far out of our comfort zone, the changes are more likely to last. Your article can apply to women as well as men. I talk to my women image clients about “baby steps.” Its probably easier for men to hear about gradually transitioning. Bravo Robert!
    Nancy Goldblatt, WardrobeWizard

  7. Jackson on

    Unrelated to the article, but has anyone purchased anything from Gagliardi, the clothing store whose ad is on the right hand side? They opened a walk in near me and since I have very limited options and can’t purchase online I was thinking of getting some of their pants.