A Step-by-Step Guide to Dressing Well

As men, we don’t really have an idea of how to dress. Usually it’s done by some maternal figure (moms or girlfriends mostly) and we are left with choosing our lounge wear, which is usually our old, barely fitting college shirt we got freshman year and a pair of gym shorts we leave on our bedroom floor. There’s always that one guy in the friend group or at the office that always seems put together no matter what setting he’s in. Maybe it’s his workout routine?Maybe he has a stylist?Maybe it’s Tiege Hanley? 

“How do I become that guy?”

Answering this question leads to more problems. Google is handy, but ends up giving you too much information to sift through. In order to sift through the noise, you need a system that doesn’t require a ton of information from “experts”. Who better knows your stye and what you like than you? We’ll put the power of personal style in your hands with this step by step guide.

"How do I get started?"

You want to start dressing better but don't know where to start.Hopefully, this guide will help. By creating a process that you can follow we eliminate a lot of the paralysis that comes with a huge amount of available information. We’re guided on principles and practicality rather than what’s flashy and trendy.The main goals of developing your style when you first start out are:

  • avoiding information overload and the resulting paralysis by analysis

  • ‘shotgun shopping’ and buying a ton of items at once because you googled and found a basic wardrobe set

  • have a solid starting point to expand from and explore your own fashion related goals

What we’re trying to do is refine and simplify to create a base for future experimentation. While we want to have our own unique style, we also don’t want to waste energy having to decide what shirt goes with these shoes when we just want to grab a beer with friends.What this guide will do is give you enough information to focus on one piece of clothing at a time. Figure out what you wear and why and using that as a basis for your clothing decisions rather than a list of style staples or wardrobe lists.

The Process

1) Research Relentlessly

2) Take a Good Look at Yourself

3) Pick One Item You Already Wear (a lot)

4) Figure out what works for you - More Research!

5) Try Before you Buy, and Purchase

6) Integrate Into Your Wardrobe

7a) Lather, Rinse, Repeat


7b) Try New Items And Styles One At A Time

1) Research Relentlessly

Find sites and profiles that expose you to different types of style. Go through articles and discussions on these sites and learn the ‘language’. Google is your ally. If you have a question put it in and find a reputable source to answer. Save pieces in places like pinterest or imgur. Even instagram has ways to save collections of fashion related posts.Some of my favorite sites are:

  • Primer

  • Dappered

  • /r/MaleFashionAdvice

Keep an open mind, but know what type of things you are comfortable with wearing and find sites and accounts that give you inspiration. I was firmly against anything but gym shorts yet now can’t see myself without a pair of chino shorts.

2) Take a Good Look at Yourself

Find what you wear the most often in your daily life. You can group this into things you wear to work and casually most of the time. Are you laid back and wear sneakers, jeans, and a t-shirt? Preppy casual with leather shoes, slacks, and a button up? All black everything?See what you wear the most often and list those common items. We are concerned with finding what works for your lifestyle, and executing perfectly on it. Double down on what you know and are familiar with so that you can stand out.

3) Pick One Item You Already Wear (a lot)

Out of the previous step, what is the one thing you wear the most? What is one item that would give improve your look the most? What item are you willing to splurge on?We want this piece to be a foundational item to your wardrobe, and that provides impact to your look from day one. To make it easy, focus on the shirt, the pants/shorts, and the shoes. You wear these the most anyway, so you’re already comfortable with wearing it, and it is embedded into your lifestyle. 

4) Research The Heck Out Of It (and figure out what works for you)

Find where the item you picked it being sold, research the quality, fit, material, feedback, etc. This is where you can determine your price point and have an idea of where to be looking.

5) Go Shopping (Try Before You Buy), And Purchase

You have a ton of options to try on the piece. Amazon wardrobe is one service that makes it easy to try on and return items if they don’t fit. Other retailers offer return shipping so you don’t have to worry about paying for it if it’s too big/small. Key things to focus on when trying things on:

Can I move around comfortably in this?

Yea the jeans hug you in all the right places, but if it doesn’t pass the squat test, or it about to burst at the seams, do you want to risk a ripped pants situation?

Does this cut complement by body style right now?

We all know your diet starts next week, but those love handles are going to be the last thing that will melt away. Find something that fits your body type right now, not what you will be 6 months later.Take pictures and send it to someone you trust if you want a second opinion. Sometimes the internet is a good judge (MFA has threads on this where many random people can give you feedback) and sometimes it’s not. Take the feedback and realize you don’t have to buy anything just yet.Try multiple stores/fits/sizes as they are all variable. Get comfortable with talking to the associates there. They are trying to make a sale, so they will be nice to you and are more than happy to look in the back or suggest things to you in hopes of getting you to buy. Use this to your advantage to get a good idea of how everything fits.Once you find what’s good, don’t hesitate to buy it, even if it’s full price. If you have the luxury to wait, that is an option. Most of the time, it’s better to go ahead and get it if you are making good use of it anyway. The investment is well spent if it lasts through multiple wears, and since we determined that in the previous steps, you know the money won’t go to waste.

6) Integrate Into Your Wardrobe

Start wearing what you just bought. See how it works in the field. Note the feedback from other people (friends, family, strangers). Look at how it fits with your current wardrobe. This will give you ideas on what to update or change next.

7a) Lather, Rinse, Repeat

The process is evergreen, as we aren’t shooting for perfection but improvement from the average. Now that you’ve updated one piece, it’s time to start at step 1 and see what item is next on the list. This doesn’t have to happen the next day, week, month, or year. It does have to happen though. Have some ideas in the back of your head, and keep collecting inspiration from places you visit.


7b) Try New Items And Styles One At A Time

Once you run the system a few times, you’ll have a base wardrobe with things you constantly wear and fit the criteria you want. Although they are good pieces, wearing them all the time will make it stale. Since we have a good foundation to build upon, we can now explore different styles away from what we usually wear. If it doesn’t work out, we can fall back on the base.


When picking a new piece to try out with your wardrobe, stick to one or two items. This helps with keeping your focus on an individual piece. Also, this is the only time where you can find cheaper alternatives to what you want to try. We want as little impact as possible when experimenting, so going towards more budget brands that have the same form factor helps in the long run if you end up not liking it.Put in a realistic time frame, spending about a month or two on an item of clothing will get you a basic wardrobe in less than 6 months. Feel free to use this process for your accessory items as well (watches, necklaces, etc), but save them once you have the base set up. This process gets addicting as the feeling of constant improvement motivates you to iterate even more. Your outfits pop because they are exactly what you want, and because you wear it consistently it gets plenty of use.Congratulations, you’re on your way to creating your own personal style.

UncategorizedGJ Sequeira