How to build your wardrobe from scratch by starting with the basics

Do you ever get overwhelmed with all of the latest trends? Are you looking for a simple way to begin to build your perfect wardrobe?

I get a lot of questions from men overwhelmed by all of the options out there. It can be intimidating to start a wardrobe from scratch. Where do you start? How do you know what color shirts you need? Or what style your shoes should be?

Never fear, I’ve got your back! Over the next several columns we are going to begin a wardrobe journey. I want to venture through your closet and help you build the best wardrobe from scratch. I want you to know that it is possible to build a closet from scratch and not drown in all of the possibilities.

We will start with the very first thing you put on: your underwear. You may be thinking to yourself, “Judah, does my underwear even matter for building my wardrobe?” My answer to that question would be an enthusiastic, “Yes!” If you want to build a wardrobe full of proper-fitting, stylish clothing, you need to start with the very first thing you put on.

Not sure what underwear to wear? Let’s discuss.

For us guys, there are three main categories of underwear: briefs, boxer briefs and boxers. I’m sure all of these styles have some sort of benefit, but my best recommendation for all body types to elevate their style is to choose a boxer brief.

When your clothing fits properly, boxers will only create awkward bulges and unflattering shapes underneath your clothing. While briefs will work better than boxers for maintaining your shape and elevating your look, boxer briefs are going to highlight your shape better and offer the best support.

My advice: wear briefs if you cannot get comfortable with the idea of boxer briefs and eliminate all boxers from your wardrobe. (Check out Tommy John’s for stylish and comfortable basics.)

OK, now that we’ve talked about the style of your underwear, let’s discuss colors and quantity.

Let’s start with a blanket statement: Your underwear should not reflect the maturity of a15-year-old. Phew! Now, that we got that out of the way, let’s carry on.

To build your underwear collection, start with the basics. Go with black, grey and navy. As far as quantity goes, I would try to have around two weeks worth of your briefs of choice on hand. Start off with five pairs of black, five pairs of grey, and five pairs of navy. That is a great basic men’s underwear collection.


I think it is worth mentioning that white underwear is always off limits.

It is way less forgiving with stains and such than the colors mentioned above. It is just plain unflattering to sport white underwear. I can think of only one exception: if you have a lighter fabric pant that is somewhat see-through, then (and only then) should you wear white underwear.

There is one last subject to discuss in terms of a basic underwear wardrobe.

If you workout, do manual labor, or anything related to physical activity, you should add workout underwear to your repertoire. Chafing is no fun to deal with and you can eliminate it completely if you wear the right underwear. For every day that you do physical activity, you should have an extra pair of workout underwear on top of your other 15 pairs. (This underwear from Under Armour is great for workouts.)

I think that is enough underwear basics for you to get started. Just remember, the way you start your look matters. Having great underwear is important for any man’s closet.

I hope you will join me as we continue on this wardrobe journey. Building a stylish closet can be overwhelming and seemingly unachievable with the plethora of options we have available to us, but stick with me and we will break down the options step by step and little by little. We can do it together and I am confident that if we take it slow and start simple, you will feel ready to tackle your complete wardrobe by the time we finish with each topic.

Do you have a specific question about building your closet from scratch? Is there a topic you want to make sure I cover? Let me know.

Judah Estreicher is the CEO of JBD Clothiers in Baltimore. Reach him at [email protected].


Leave a Reply

Your email address will not be published. Required fields are marked *

Jbd Logo-JBD Clothiers