10 Big Wins To Help You Dress Sharp, Look Handsome, And Shock Your Loved Ones

by Barron Cuadro  |  in Style Tips

One of my favorite sites is I Will Teach You To Be Rich, run by Ramit Sethi. Originally only about personal finance, IWT now focuses on using psychology and systems to live a Rich Life.

Many sites in the personal finance niche talk about cutting back and saving a few cents by not buying that latte every morning, or not going to the movies every weekend.

Ramit takes a totally different approach.

He tells his readers to buy those lattes and watch those movies, and instead of sacrificing enjoyment and pleasure to save a couple cents (and hating your life in the process), focus on those five to ten Big Wins that will save you hundreds or thousands of dollars.

I totally agree with this philosophy.

And then I started to wonder, how can the Big Wins strategy apply to improving your personal style and dressing more sharply?

When you think about it, upgrading your personal style is all about accumulating a series of Big Wins.

If you think to yourself, “Okay, I have to start looking and dressing better,” you’re sabotaging yourself before you even start, because that goal is so large and abstract with no concrete starting point.

Beginner You can’t even fathom the idea of Stylish, Put-Together You.

Even worse, you might go for the little, misguided wins, like buying a bunch of cheap, trendy crap without even knowing what your goals are or what you’re trying to achieve.

You need easily-achievable, clearly-defined Big Wins that produce significant growth and change in your personal style, wardrobe, and self-confidence.

Below are ten Big Wins that will take you closer and closer to being that handsome, sharply-dressed, well put-together man. You may already have a head start, and some of these may be more important than others in your particular situation.

I encourage you to attack each one head on. By doing so, you can’t help but improve and get closer to your goal.

Big Win #1: Figure out your Why

It’s important for your own progress and sanity that you understand what your reasons are for wanting to dress better. Your “Why”.

Are you improving your style because you want to…

  • look and feel better?
  • be taken more seriously?
  • impress your significant other / relatives / friends?
  • get the girl?
  • get the promotion?

You get the idea. Having your end goal in mind is important because you can create the wardrobe you need to help you meet those goals.

Also, knowing why you’re making the effort in the first place can help guide your decisions.

For example, if you’re trying to make a better impression at work and need sharper business casual wear, you’re not going to spend all your time finding the best pair of raw denim.

Understand why you want to improve your style and how you want to be perceived, and figuring out the details of your future (lean) wardrobe will be much easier.

Big Win #2: Reframe your mindset

It’s always a little intimidating doing new things, stretching your boundaries, and venturing out of your comfort zone.

At some point, you have to stop being scared and start experimenting with the changes you want to make. Keep your eyes on the prize and ignore any comments or feedback that may sidetrack you.

Stay out of your own way, too. Remember that most negativity projected onto you is a reflection of how that person feels about him or herself. Gandhi or Mr. Rogers once said something like that, probably.

Regardless, it’s totally true.

Somewhere deep down inside that poorly-dressed body is a sharp and dapper dude. Start believing in yourself and taking the steps you need to improve your appearance. A sharp sense of style equals a good first impression, whether or not you want to believe so… and first impressions are everything.

Big Win #3: Read. And read. And read some more.

I’ve published hundreds of articles since I first started EG back in 2009. Go through the archives and immerse yourself in this stuff.

I even create courses and write eGuides that help you step by step, whether you’re 15 or 55.

Video more your thing?

Check out MenDotStyle’s YouTube channel. Their In The Closet series should be particularly useful, though you may find the other playlists entertaining and insightful as well. They haven’t uploaded videos in the past few years, but the ones that do exist are still very relevant.

Of course, our friend Antonio from Real Men Real Style has hundreds of videos on his YouTube channel. Go ahead and dive in; I’ll catch up with you in a few weeks.

MR PORTER does a great job on YouTube and I’m sure you’ll find inspiration there. I like their The Way I Dress playlist the most.

It’s a bummer GQ’s and Esquire’s YouTube channels don’t have much style-focused video content, but if you like watching behind-the-scenes shoots with models and actresses, they’ve got you covered. To their credit, GQ does have some useful playlists, you just have to dig a little.

Big Win #4: Find your cheerleaders

Everyone needs a little encouragement once in a while.

Hang out with people who are open to the positive changes you want to make, who have already made those changes, or whose style you look up to.

In work and business, this makes all the difference in the world, and the same can be said for the company you keep when you’re off the clock as well.

Simple, right?

Big Win #5: Take casual inventory of what you have, what’s worth keeping, what needs to go

Once you have a grasp on what you have, what you need, and what you have but don’t need, it’s easier to plan your next move.

If you’re diving head first into that Lean Wardrobe closet transformation, you’ll want to take this Big Win extra seriously. But really, any degree of diligence paid to this task is a huge win.

Lots of times, we get comfortable with what’s easily within reach, even if it belongs in the “Have But Don’t Need” pile. Taking inventory of your wardrobe and separating everything into groups will help you compartmentalize and prioritize your needs.

After going through the item separation, the next step would be to get rid of the “Have But Don’t Need” pile. That will 1.) clear out room in your closet, which actually feels great (mentally and physically) once you do it, and 2.) prevent you from defaulting to those ill-fitting, old garments that don’t do you any justice.

Upgrading your personal style is all about accumulating a series of Big Wins. (Tweet this!)

Big Win #6: Take your measurements

Once you’re in the replenishment phase, you’ll be replacing and buying new items to complete your Lean Wardrobe.

Before you even think about buying anything, it’s a good idea to take measurements of your best-fitting garments. This will prove extremely useful when buying clothing online.

It’s easy to skip over this Big Win and just assume a medium shirt is a medium shirt, or a 32×30 pair of pants is always a 32×30. Sadly, this isn’t the case.

Many online stores provide specific measurements for their garments, and having a handy dandy list with all of yours written out makes things so much easier.

This could mean the difference between you owning an item that fits perfectly and receiving something that doesn’t fit at all.

Let’s not even discuss the painful return process of most online stores. Just spend 10 minutes doing this and save yourself weeks of waiting for your return to arrive and your refund to process (ugh).

Start with a few key body measurements: Chest, sleeve length (both from shoulder, and three-point system), natural waist (narrowest part of your torso), waist across your belly button, hips (widest part of your bottom half), and inseam.

Also measure your best fitting dress shirt, pants, and sport coat.


  • waist
  • chest
  • length (from bottom of collar in back)
  • sleeve (from shoulder, and three-point)


  • waist (across waistband)
  • inseam
  • rise (top of waistband in front, to crotch seam, to top of waistband in back)

Sport coat

  • chest
  • waist (across top botton of a two-button suit)
  • jacket length (from bottom of collar in back)
  • sleeve length (from shoulder, and three-point)

Big Win #7: Figure out what fits

The best way to figure out what truly fits is to try stuff on. Take several different sizes into the fitting room with you.

Let’s assume you’re a 32×30. If you’re shopping for pants and you’re trying a new brand you’ve never worn, take a 31×30 and a 33×30 in with you as well.

Also, pay attention to the fit descriptions of each item. Slim, straight, tapered, skinny… all these words mean something, but they’re different depending on the brand you’re wearing.

Unfortunately, not everything labeled “slim” fits the same across all brands, so it’s important to try everything on first to see what works and what doesn’t work for your body type.

Big Win #8: Buy a suit

Just one suit.

What should it look like? Single breasted. Two button. Notch lapel. Double vented (if possible). Solid, all-season fabric (worsted wool will do). Slim, but not skinny. Modern and contemporary, yet classic. No pleats (unless they’re necessary). No cuffs (unless that’s your thing).

Color? Choose one: Navy or Mid-grey.

Not a suit guy? You’ll need it some day. Trust me. When that day comes, you’ll be thanking me under your breath.

Big Win #9: Starting from scratch? Upgrade slowly

While I encourage you to dive head first into the process of the Lean Wardrobe, I don’t suggest diving head first into buying and replenishing your closet.

I mean, you could, but then you’ll end up buying a whole lot more than you need, or you’ll purchase things that don’t fit, or some other similar, unfortunate fate.

It’s not worth it. The point of the Lean Wardrobe is to save you money, not cost you more than you’ve already spent.

Spend time learning the basics first (completing the Big Wins above certainly helps), and then begin to upgrade when the time is right.

And do so slowly.

Take your time, and do your best to stay on track from the very beginning.

Nervous about the whole upgrading process? Keep things smooth. Here are some ways to do that.

Big Win #10: Build that Lean Wardrobe

Always remember, it’s all about simple garments in classic, muted colors that comprise the base level of your wardrobe.

You can build upon this with accessories and garments that have bolder color, pattern, and texture.

What are some Lean Wardrobe items you’ll need? For starters: a great pair of denim, a couple OCBDs, a handful of sweaters, a well-fitting sport coat, a few pairs of great leather shoes, a warm coat, and of course, that suit I already told you to pick up (here’s how to buy the right one).

Once you’ve picked up these items, it’ll be easier to fill in the blanks of your closet, since you can see what you still need and what you don’t.

If you want a proven step-by-step process, check out our course.

In Conclusion

Accumulating those Big Wins to develop your personal style may be time-consuming, but in the end, totally worth it.

You’ll save more time (and not to mention money) just following the process and checking each one off your list.

Which Big Wins have you already scored? Which ones are you continuing to work on?

I’d love to hear your stories in the comments below.