Starting To Dress Well In-Depth Guide

Starting To Dress Well In-Depth Guide by TedMitchell

This guide is:

  • An outline for how to build your wardrobe
  • A base for which to move forward into developing your wardrobe and style

This guide is not:

  • A shopping list
  • A guide on a specific fashion style
  • A guide on fit

This guide is intentionally general, it serves as a base for which other guides will build off of.

Step 1: Taking Inventory

A lot of people start off lost, knowing that they want to change the way they dress but not knowing how. The easiest way to find your footing is to affirm exactly where you are, then use that to have a clearer understanding of where you want to go.

This step is exactly what it sounds like, take inventory of everything you own. Everything. From your shirts to your socks, knowing what you have will allow you to move to the next step with improved focus.

How detailed you make your inventory is up to you, but the more detail you provide the easier things will be down the road.

To assist with this process, here is a spreadsheet created by WebLlama a few years ago. I suggest reading the entire post because it’s full of great information and is a good example of the kind of process this guide is meant to facilitate.

For example it may be easier to write down that you have 20 shirts in your closet. But that provides a lot less useful information than noting that of those 20 shirts, 10 are t-shirts, 5 are long sleeve, and 5 are long-sleeve button downs. Then you can even go further and say that of those 10 t-shirts, 7 are graphic-tees and 3 are solid colors. So on and so forth until you have a list that is as detailed as you like.

The purpose of all this is that you can’t possibly know what you need unless you know what you have.

note: you don’t actually have to write anything down, but I strongly suggest it.

After taking inventory, the next thing to do is separate what you have into two categories: things you wear often and things you wear rarely. This segment is aimed towards “main” clothing, so shirts/pants/shoes. You can go further and do outerwear and underwear/socks if you’d like.

To provide a general idea, let’s say:

“often” = about 8 times a month (twice a week) and “rarely” = about 2 times a month (once every two weeks). Of course tweak this to suit the size of your wardrobe and account for mandatory clothes (uniforms, etc.)

Just remember that there is no discrimination here, but if it helps think of the “often” pile as being what you’d consider your “essentials”. If you had to pack for a week, what would you bring?

When you’re done, look at it and compare it to the list you made before. Feel free to create another list containing only the things in the “wear often” pile, it should help you get a comparison of how your wardrobe was made up.

When you’re done, it’s time for the next step.

Step 2: Culling the Weak

If you were truly honest with yourself in Step 1, the “rarely wear” pile should be around half of what you own assuming you have an average sized wardrobe.

Now you need to get rid of it. Place the rarely worn items into a separate archive box in case you wish to go back to them later and reevaluate, or use them for something else down the line.

Removing those rarely used items does two things.

  • The first is that it lets you know what you care about and what you don’t. Over time clothes build up because most people don’t sell/give away old items. This leaves you with pieces that are underused and only serve to take up space and give the illusion of having a full wardrobe. Taking inventory, splitting into categories, then removing these unused items lets you know what you really have.
  • The second is that it gives you space, both literally and figuratively. When building your wardrobe back up it’s important to be conscious of the amount of clothes you acquire. The point is to satisfy your needs without accumulating an excess.

This step is arguably the most important because it is the repeating step. You’ll have to do this one again to remove the clothes that don’t fit your desired goal.

This will be touched upon later, but for now this is all you need to know to move on.

Step 3: Asking the Right Questions

Now that you know what you have it’s time to figure out what you need.

The only way to get there is to ask the right questions. Here are some examples:

  • What about my current clothes am I dissatisfied with?
  • What about my current clothes am I satisfied with?
  • What clothes are appropriate for my current position (in life)?
  • How do I currently feel?
  • At the end, how would I like to feel?
  • Do I want to be simple and sharp, or make a statement/expressive.

And answers to these questions:

  • I’m dissatisfied with the way my clothes fit on me. I also dislike that they are mostly dark colors like black and grey. They are out of touch, way behind the current trends.
  • I’m satisfied with the types of clothes I wear. I like jeans, t-shirts, and simple shoes. I’d just like to have better options.
  • I’m a college student so I’m mostly dressing for that environment. Though I’m looking to get an internship soon so some formal wear may be needed in the near future.
  • I feel unsatisfied and a bit insecure.
  • I’d like to feel clean, confident, and stylish.
  • I just want to look good, keeping it simple and not doing too much. At least for now.

Once you’ve developed these questions and answered them, it’s time to make use of the first two steps and relate them to the answers you found.

Step 4: Making a Plan

This is where the plan comes together.

By taking the information gained from the first three steps, it is now possible to start the process of finding the direction you’d like to go with what you wear.

To use the example from step 3, the goals that could  be developed could look something like this:

  • Stick to t-shirts, jeans, and simple shoes.
  • Incorporate more colors (lighter blues, reds, whites, etc)
  • Keep the clothes simple, but stylish.
  • College appropriate styles, keep it trendy
  • One or two outfits for internship/office environment

Just like that there is knowledge and direction, the thing that most people come to MFA to look for.

Once these goals are set, go back and look at what was in your “often wear” pile. Has your feelings changed to anything in there? Do the items in there relate to the new goals you have set?

If not, consider redoing step 2 while keeping your goals in mind. This time try dividing them based on what fits within your goals and what detracts from them.

While you’re at it you should also start thinking of a budget. This will come into play later when you start to advance into actually buying clothes to achieve your goals.

Once you’re done, it’s time to finish up.

Step 5: Taking the Next Step

We’re finally here. Good job for sticking through, now let’s wrap it up.

To summarize where we’re at, you should now have the following:

  1. Knowledge of what clothes you wear most
  2. Knowledge of what questions to ask yourself moving forward
  3. A plan of what you want to accomplish/goals you wish to achieve
  4. (optional) A budget

All of this so far was meant to create a base level for you to work from. The next step is to further expand your knowledge with research.

But knowing what you want and knowing what to buy are two separate things, and as mentioned in the Contents section this guide is not a shopping list. There are other resources for that.

Use the search bar on MFA, participate in the weekly threads, try and get as much information as possible and always relate it to the goals you have set.

If you’ve followed the steps within this guide well, then you should always be able to ask the right questions and receive quality answers. You should always know exactly what to search for and recognize when you’ve found what you’ve sought.

There will always be people willing to help you, and bringing forth a solid foundation is the best way to help yourself.

Happy hunting.

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