A few years ago when I was still working a 9-5, I was sitting at my computer, drinking my coffee and getting settled in.

My coworker at the desk area next to mine was checking email and minding his own business… when another one of our colleagues (let’s call him Andy) walked by on his way to the printer.

Andy jokingly said to my desk neighbor, “Man, that sweater, again? Is it yesterday already?”

He was a funny dude so we knew his joke wasn’t mean-spirited. But it got me thinking: even if that’s just a playful jab, deep down, there’s a reason he said it.

It’s easy to fall into a routine with your outfits. If you don’t switch things up after a while, your looks can go stale.

We tend to repeat the same combinations over and over. We stick to what’s safe, to what we know works.

Even if no one’s ever confronted us about our repetitive looks, what if we’re simply tired of wearing the same thing all the time?

If you’ve ever wanted to switch up your look, try one (or all) of these outfit tweaks to step away from your “usual” and experiment with something slightly different.

Who knows, you may find new combinations you never thought you could pull off 🙂

By the way, shout out to the guys at Ace Marks for sponsoring this article and making the great shoes you see in tweak #1.

Looking for high quality, well made, unique leather shoes? Want something a bit different than the typical brown and black oxfords you’re used to seeing out there? You’re going to want to check them out.

1. Go bold with one item, keep everything else neutral

Successfully matching multiple colors and patterns can be tough. Same goes for incorporating several stand-out or trendy pieces into your outfits.

The best thing to do is to stick to one bold item. Keep everything else in your outfit a neutral color and stylistically middle-of-the-road.

What exactly is a neutral color? When it comes to clothing, these are the colors I’m talking about:

three outfit tweaks neutral colors

From L to R, top to bottom: Black, charcoal, light grey, brown, British khaki or caramel, light khaki or ivory, olive, navy, white

While not all of these are neutral in the traditional sense, we consider them neutrals because they all pair well with each other, and with other harder-to-match colors (think salmon, eggplant, mint green, etc.).

And of course, if you wear multiple items of clothing that scream, “Look at me!” it can come off as tacky or misguided. Especially if you’re not a rock star, actor, or someone with a huge personality that may or may not have a stylist who knows how to pull it off.

Keeping your outfit neutral in both color and style, and incorporating your one bold item is a great way to break out of boring and bring it up a notch.

That way, you have one stand-out piece that draws attention and isn’t competing with anything else in your outfit.

For extra style points…

Go bold with your shoes. This is a totally unexpected style move, since most guys typically go for a bold tie, a printed shirt, or something similar.

Ace Marks does this well. They know how to design bold shoes without going too over the top.

Not to mention, they’re made in Italy by the same craftsmen who also happen to work with and make shoes for high-end luxury brands. So you’re essentially getting the same quality shoe that may sell for $600+ under a luxury brand name, but in the sub-$300 range.

Ace Marks is in a class all its own and the perfect choice for those who want to take a step or two away from strictly traditional styles.

How to do bold right

Let’s use a nice pair of oxfords or bluchers as an example.

You can go bold with a shoe that is made from complementary materials and textures (in this case, suede quarters on a leather shoe), or two different colors (this is oxblood mixed with dark grey, subtle, yet different).

As you can see, neither are too garish or in your face. But they’re different enough to pique someone’s interest… to set your shoes apart from the sea of brown and black oxfords out there.

This is the key to successfully incorporating color, even if you’re scared of mismatching or clashing. Stick to an outfit full of neutrals, and with one bold piece, you can’t mess up.

Out with the old, in with the new

In case you’re interested in checking out a pair from Ace Marks, this might sway your decision.

For a limited time, their Buy Back program encourages you to send over a pair of your old dress shoes, and you’ll get a $50 credit towards a new pair.

Instead of leaving your old (yet still in good condition) dress shoes sitting in the back of your closet unused, you can earn credit towards a brand new pair you’ll love using.

Best of all, Ace Marks will donate your shoes to Career Gear, a leading national organization that helps men in need get back on their feet and re-enter the workforce.

Pretty cool, right?

You can check out more from Ace Marks here, and if you plan on picking up a pair, use code “Effortlessgent” at checkout. You’ll receive 10% off for being an EG reader!

2. When your outfit goes low, have one piece go high (or vice versa)

Not only were Secretary Hillary Clinton’s pantsuits on point this past campaign season, so was her bit of sartorial advice that actually came from the FLOTUS herself.

OK, so maybe FLOTUS wasn’t giving everyone sartorial advice when she said that. But it’s actually surprisingly useful for those trying to break out of their boring outfit combinations.


Regardless of who you supported this election, here’s how you can apply this idea of high and low.

There’s something I call the Spectrum of Style Formality that comes in handy when putting together outfits.

For example, say you were planning on wearing a suit today. Instead of wearing a topcoat (typical outerwear for an outfit that skews more formal, as the Spectrum shows), throw on a military-inspired jacket instead.

three outfit tweaks suit military jacket

via The Sartorialist 1, 2

As an example of going the opposite way, you can take the topcoat (more formal, as I mentioned) and wear it with a casual outfit.

You can do this with almost anything in your wardrobe. You’re basically swapping out your usual for an alternative. It’s the basis of the high/low styling method I’ve talked about before.

When putting together an outfit, we usually wear everything from the same location on the Spectrum. By making sure one item is from a different part of the Spectrum, we add a bit of unexpected visual interest to our overall look.

So instead of jeans, try trousers, keeping everything else the same.

Instead of a top coat with your suit, try a military jacket.

Wear double monks with jeans and a varsity jacket. (These are the pair of double monks I have.)

Throw on sneakers with your (perfectly tailored) grey trousers.

You get the idea.

3. Adopt the Rule of Three

Stylish ladies know this rule. Retail associates at your favorite stores know this rule. It’s time you adopted it as well.

Outfits are made of at least two items of clothing (not including your shoes). Jeans and a long sleeve henley, trousers and a dress shirt, etc.

What makes an outfit really come together, is a third piece of clothing. So, jeans, long sleeve henley, and a quilted vest. Trousers, a dress shirt, and a cardigan.

Let’s break it down:

  • you choose your bottoms (first piece),
  • your top (second piece), and
  • your third piece would be a blazer, a jacket, a vest, sweater, or some other layer.

Sometimes, accessories may work. Think a scarf in a casual outfit. But a tie on its own wouldn’t be considered a third piece since a shirt and tie without a jacket isn’t really a complete formal outfit (unless you’re a ten-year-old schoolboy).

Pay attention next time you see a great outfit.

Most likely, there will be at least three elements to it. There’s a good chance it’s made up of more than three, when you add in a coat + accessories.

First outfit: Chinos and OCBD (1st and 2nd item), sweater (3rd), sport coat (4th), sunglasses (5th), portfolio (6th).

Middle outfit: Chinos and sweater (1st and 2nd item), quilted vest (3rd).

Last outfit: Chinos and dress shirt (1st and 2nd item), sweater (3rd), sunglasses (4th), bag (5th).

Don’t be bored with your clothes, have fun with them

I know how easy it is to fall into an outfit routine.

There’s something to be said about having a uniform (and I’m totally pro-uniform, by the way). But sometimes, we want to break out of that and try something new and different.

At the same time, it can be hard to break out. The things we try on a whim just don’t look right.

Giving yourself enough time is key. That means throwing on a completely new look on a random Tuesday morning when you’re already running late for work is not a good idea.

And make sure to use these three tweaks. They’re small, but taking advantage of them will change up your look enough to get you excited – yet not so much that it’s completely jarring and makes you feel uncomfortable.

Remember the shoes from Ace Marks I mentioned in tweak #1?

Give them a shot so you can go bold with your footwear. The folks at Ace Marks are offering EG readers a 10% discount. Just use code “Effortlessgent” when checking out!

Make sure to let me know which ones you chose in the comments below 🙂 And if you’ve applied any of these tweaks, I want to hear how they worked for you!

Got a question? Hit me up!

Comments are old school, though. Why not tweet at me or DM me on Instagram?