Better Dressed Butch: Versatile Casual Winter/Spring Wardrobe – Part 1

One of the hardest parts of starting to dress better is putting outfits together.  Most people think of clothes in terms of outfits, so when they go shopping for new clothes, they usually buy a couple of new outfits without thinking about their overall wardrobe.  This approach doesn’t work.  You’re left with the same old wardrobe, plus two new outfits.  So you now have two days that you feel awesome in your new outfits, and all of the other days you are stuck with your same old broken wardrobe.   This approach is not going to get you to the place where you are well-dressed every day.  Even if you bought enough new outfits for several days, you are going to end up bored with wearing the same several outfits over and over again.

There’s a better way to build your wardrobe.  If you approach your wardrobe as a whole, you can buy individual pieces that all work together.  And if you have assembled a wardrobe where the pieces can be worn in multiple outfits, you will be a better dressed butch much more quickly.  Let’s look at how to build an affordable, stylish and versatile wardrobe that will give you a ton of options with a minimal amount of items.  

We start building a great wardrobe piece by piece.  The key here is to pick separate pieces that each pair with all of your other pieces.  This means each of your shirts can be worn with each of your pants.  It means that your color selections are very focused to begin with: gray, navy, black, tan, and olive.  Not only do these colors look good on everyone, each color works well with the other colors.

Some people might protest that this approach is “boring”.  They think that having a closet full of items in neutral colors leaves you without options, but, as we will see, that’s simply not true.  But as we will see, pairing neutrals colors together does not have to mean boring.  It will give us a ton of options for creating more outfits than you can imagine.

Personally, I would rather have the ability to look good every day instead of having only two or three great outfits.  Also, remember that this is an incremental approach – we’re going to start with basics as our foundation.  The foundation will serve as the base for us to build a creative wardrobe.  We start with simple, versatile pieces.  And then we start to add pieces with more color and pattern.  This allows us to craft a great wardrobe from the start, so we can buy a minimum number of items and get a maximum return.  Then, every additional item we add gives us several new outfit choices because we can pair our one new shirt with each pair of pants, and layer that one shirt with each of our several outer layers.  Once we build the foundation, each addition to our wardrobe gives us exponential new possibilities for outfits.

I want to be specific, since clothing changes seasonally.  So let’s work with our winter/spring casual wardrobe. The items here can be layered, which gives us the ability to wear them through a variety of temperature changes.  With all of the mood swings in weather, this adds yet another layer of versatility to our wardrobe.

By casual, I mean that these are the clothes you put on after you get home for work, or on the weekends.  These are your hanging out clothes.  Here’s what a very basic casual winter/spring wardrobe, built completely on our focused colored selections, looks like:



Clockwise from bottom left we have:

  • 4 pairs of pants
  • 4 button up shirts
  • 2 sweatshirts
  • 4 long sleeve shirts
  • 5 sweaters
  • 3 belts
  • 4 pairs of shoes

That’s a total of 26 items.  And we can put together literally hundreds of outfits from these basic selections.  That is a lot of versatility.  How can that be boring?

Beyond the sheer number of outfits you can put together, there’s another reason these choices are not boring.  While these items share similar colors, there are a variety of details that make the individual pieces stand out.  For instance, the chambray shirt adds an interesting texture; some of the long sleeve shirts are henleys, while others are thermal; and each of the sweaters has a different texture or pattern or thickness.  So our individual choices add to the variety and keep this wardrobe from feeling stale or like every thing you wear is exactly the same except for color.

By picking interchangeable items for our foundation, we can exponentially increase our options with each item we add.  Each shirt below can be worn with each pair of pants.  Here’s how the numbers work with a versatile wardrobe:


This is over 2 weeks worth of different outfits from only 8 items.  Contrast that with having only 2-3 days worth of great looks when you buy 2-3 new outfits that aren’t versatile.  And we could switch out any of the other set of shirts (long sleeves or sweaters or sweatshirts) from our wardrobe up top and get similar results.  If we put the long sleeve shirts in place of these button up shirts, we would have a further 16 outfits.  Using the sweaters instead, we would have 20 outfits.  And that is 20 additional  outfits.  So just using one shirt and one pair of pants, we would have 16 outfits using the button up shirts, 16 outfits using the long sleeve shirts and 20 outfits using the sweaters.  That’s over 50 different outfits.  You can being to see how this versatility gives a maximum number of options.

Where the real magic happens, though, is when we begin layering.  Watch what happens when we add just two more items that can be layered over our shirts:


That is a lot of variety added from just 2 new pieces.  48 additional outfits, on top of the 50+ outfits we have before we start layering.

Now, full disclaimer that the math doesn’t tell the whole story here because the numbers assume that every item works perfectly with all of the others.  I would probably never choose to wear that dark blue shirt with the navy sweatshirt, for example.  But this does illustrate how adding only 2 items drastically increases the number of outfits we can put together.

Let’s look at some more examples: What if we take the 2 sweatshirts away and replace them with the 5 sweaters from our wardrobe:


This is still only 13 items of clothing and we now have another 90+ outfits we could put together.  That’s a different outfit every day for nearly 3 months.  And this doesn’t even take into account how each look changes depending on which shoes you pair with it.  Boring?  I don’t think so!

You can begin to see how building a versatile wardrobe with a strong foundation of seemingly simple and basic items can completely change your ability to dress well every day.  This one concept can completely change how you dress and how you shop.  After the importance of fit, I think it is the most powerful idea to grasp so you can be a better dressed butch every single day.

Now let’s see some examples of how we can create different outfits from our foundation pieces.  These outfits are all created using our versatile wardrobe pieces and run the full spectrum from casual enough for hanging out and watching movies to looking good enough for a first date.  What items would you put together to create an outfit?









To see how we can build on this versatile wardrobe foundation, stay tuned for Part 2.