Building a wardrobe is a years-long process.

Much like losing weight, building muscle, or growing a business, curating a great wardrobe doesn’t happen all at once.

There is no magic pill. I haven’t met anyone who has a completely empty closet and a spare $5,000 to fill it up.

In most cases, the process unfolds slowly, one item at a time, over many years.

And because it takes years to build something you’re happy with, your tastes can change along the way.

Here’s a real example from my own life: For years, I didn’t wear black. I considered it boring and unimaginative, and I much preferred a bit of color in my wardrobe.

I also told you guys to be more courageous and experiment with color, since black is such an easy fallback, as it goes with pretty much everything.

I still feel this way, and I absolutely think you need good color in your Lean Wardrobe but I’ve opened up to black clothing more since moving to NYC.

It must be the vibe of the city, especially in the colder months, that makes black seem much more appropriate at times.

Today, I’m going to help you add a few black clothing items into your wardrobe to give you a break from all the navy, brown, and charcoal.


Let’s start with my list of must-haves, if you are going to start wearing more black.

Leather oxfords

I’m going to mention a few other things further down the list, and with those, you’ll need a pair of black leather oxfords or bluchers. Don’t know the difference?

It’s up to you how formal you want to go. If you ask me, I’d go with a plain cap toe or semi brogue.

Sneakers and / or boots

This winter, my Chippewa boots have seen the most use.

Not only are they incredibly comfortable, they also hold up well (yep, in the rain and snow), they’re tough (for the New York concrete), and surprisingly light (must be those Vibram soles).

They do come in other colors, but I love the black leather with contrast white stitch and white Vibram sole.

For the summer, I’ll probably stick to lighter colored sneakers, but I’ve been eyeing the leather Old Skools from Vans. I love that combo of black and white, not to mention the tan inside the heel. An alternative would be the Converse Jack Purcell.

If you’re the “all black everything” type, Converse makes a great leather Chuck Taylor in all black.


I’d be surprised if you didn’t have a pair of black socks, but don’t feel limited to the polyester variety your dad kept stocked in his closet.

Also, you don’t need to stick to solid black. Experiment with texture for an extra level of interest, or patterns to incorporate other colors (think multi-striped, argyle, checked, and so on.)


Go with a black silk knit or grenadine tie for everyday wear. Black silk or satin would come in handy for formal events, or when you’re wearing a black suit and white shirt, the most minimal yet classic of combinations.

Remember to stick with a width that goes with the rest of your outfit… meaning slimmer lapels need a slimmer tie, and wider lapels, a wider tie.


The nice thing about having a dark sweater is that it can be dressed up (under a suit) or dressed down (with jeans and loafers).

It can elevate a daytime outfit or blend in nicely with an evening one. In short, it’s super versatile and worth the investment.

You’ll get a bang for your buck with merino wool. I feel these hold their shape better, and pill much less than cashmere, although this would be your next step up. Can’t beat that softness. If you take care of it—and if it is of high quality—it will last you years.


I consider the following items nice to have, because you’d get much more use out of the things I’ve mentioned above. When budget and closet space allow, consider picking up stuff from this list:


If you haven’t yet picked up your first suit, I suggest you make it navy or a medium to charcoal grey. If you haven’t picked up your second suit, I suggest you make it the other one you didn’t pick up the first time.

With your third suit, you can go many ways, depending on your situation, income, and surroundings.

One of the directions you can go is a black wool suit. You got your navy and gray workhorses, so why not own a suit for when you’re feeling extra badass?


Dress watch

Sorry, friend, your Timex on a NATO won’t cut it in this situation. You’ll need something a bit more classy and understated.

Classy + understated doesn’t have to = expensive. You can find something with a white face, black leather strap, and clean lines for under $150.


I’m thinking a basic Harrington jacket for warmer weather, and maybe a lightweight trench for rainy days.

For freezing cold winters, you may want to go with a down coat. Here’s the one I picked up when I moved to NYC.

Worth every penny, considering I was freezing to death in the warmest coat I had at the time, a navy peacoat with Thinsulate… not nearly warm enough in January.

Beanie / toque

Not sure what you call it where you’re from, but when the temperatures drop, you’ll want one of these on your head.

You can get a basic acrylic one from somewhere like American Apparel, or something a bit more luxurious.

A few months ago, I found a cashmere beanie at H&M, of all places. It was a medium gray, not black, but still… keep your eyes peeled and you may be surprised at what you can find.

Denim and / or chinos

I’ve embraced the black denim and the black chinos. It’s the next logical step after dark denim.

I pair them with everything from old white Chuck Taylors to tan loafers and navy chukkas. I tend to throw most of the color insecurities I have out the window and treat black denim like dark blue.

I suggest you try it out. If you’re slim, try the Levi’s 513. If you need a bit more room in the seat and thighs, maybe the 541 or 501CT are more up your alley. And for chinos, I usually go with the Dockers Alpha Khaki.

Gym clothes!

I love wearing all black to the gym. I feel like a fat and weakness assassin, out for the kill.

Maybe that’s just me.


If you’ve already gotten used to living without black, that’s great.

But if you’re looking to incorporate a bit more black into your life, I hope this helped you decide what to experiment with first.

Tell Me

How often do you wear black? Is it a daily thing for you? Or are you like (old) me, still figuring out ways to fit it in? Let’s hear it below!

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22 Responses

  1. Tod C on

    I was skeptical when I saw this list and then I saw I had everything except the black sweater (I usually look washed in black as I am pale). Really solid list and I personally use black to tone down an outfit too so I don’t have too many crazy items.

    I would also add a pocket square with a lot of black. Understated and a good contrast for gray and brown jackets.

    • Barron on

      that’s interesting re: pocket square with a black ground. Never tried that, and I don’t have any. I’ll consider that next time, cool idea

  2. Gus Walbolt on

    My “must have” black menswear clothing and accessories – oxfords, calf belt, silk knit tie, loafer or double monk, black leather jacket, cashmere turtleneck, cashmere scarf, knit hat.

  3. Cliff on

    Sorry but as a British man I don’t get the black suit thing. Navy and charcoal yes but never black. A black tie is best reserved for a funeral. Black Oxford shoes I do agree with and black socks are acceptable. Not keen on the black pullover and a black shirt is never acceptable.

    • Barron on

      I agree that black is best for the most formal of events. That’s why I listed it under “nice to have”.

      But I mean, look at the guys in those photos. They make the black suit work.

  4. Jean G on

    Being a native NY’er, I have too much black, lol. I’ve been trying to incorporate a bit more color in my wardrobe.

  5. Nate on

    I, too, have shunned black in recent years, but gave it another try this past winter and am back on board.

    Maybe it’s living in Chicago or maybe it was the result of watching Skyfall and Charade ( with Cary Grant) back to back that caused the change of heart.

    Great list Barron. I need to add the sweater, watch band, and jacket to my shopping list.

    • Barron on

      I don’t wear black often, but when I do, I find that having key staples make it a lot easier to incorporate it into an existing outfit.

      Daniel Craig and Cary Grant could wear garbage bags and somehow make it look cool. 😉

  6. jamessc on

    I wear black about every two weeks in fall/winter months not as often in summer. I own a black suit, top coat, sport coat, three various black sweaters, couple of pair black slacks, and numerous pairs of socks, shoes and boots in black. Do not have black jeans or chinos…..will take care of that. Enjoy your articles and you are 100% correct I did not
    get my wardrobe overnight….I am 68 and have seen many stiles come and go.

    • Barron on

      I’m sure you’ve seen many things throughout the years, especially when it comes to clothing 🙂 I’m sure the one thing that’s stayed constant (or so I assume) is good fit and proportion in your garments. Thanks for reading!

  7. fkpaul on

    As New Zealander, black tends to be our natural choice for colour (if we can call it a colour that is). And if you know anything about my country you could probably guess why. Hence the younger me had many articles in that colour, and it’s not uncommon to see Kiwi men use it as their option for their everyday business suit. When I moved to Australia several years ago I made a deliberate effort to reduce that colour from my clothing options, and opt for navy, grey and many more lighter colours to suit the warmer climate. It’s funny that this topic has popped up because over the past year I’ve been reacquainting myself with black. No particular reason, maybe I’m missing NZ. Unlike you fellas in the northern hemisphere, we down here in the southern hemisphere are now heading towards our winter. Besides the classic black tee shirt, one further item I think is a great nice-to-have is the black slim fitting dress shirt. I noticed an earlier comment saying that such an item is a big ‘no’ – well I will disagree with that sentiment. In my experience it pairs particularly well with a light-to-mid grey jacket, dark blue denim, black shoes or dress boots and belt. Depending on the weather I can use that combination pretty much year round, though it’s probably better suited to the Autumn/ Winter season. Cheers!

    • Barron on

      i agree with your disagreement, in that there isn’t a definitive No for any article of clothing. it depends on your situation and surroundings, e.g. it’s normal for you but perhaps not normal for him.

      in any case, glad you were able to step away from black just a bit and are now coming back around and using it again.

      I actually don’t know why Kiwis naturally gravitate to black clothing. Feel free to enlighten us all 🙂

      • fkpaul on

        Haha sure ! New Zealand is a Rugby playing nation. Lets just say we are ‘passionate’ about that game. And for many years we have had arguably the best rugby team in the world called the All Blacks, named so because their uniform is totally black. The game and the team has been a significant source of pride and a major influence on our national sense of identity. With the exception of our national soccer team (funnily enough – called the All Whites for the same reason) pretty much every sports team and sportsman representing our country at international sporting events will be clad in black. Where the Aussies clad themselves with green and gold, Americans are patriotic for the red, white and blue, we Kiwis have claimed the black. Actually we are all secretly happy about that, it allows every Kiwi to be stylish while remaining patriotic.

  8. AaronRichards14 on

    You know how long I’ve waited for black to be labeled as “trendy” again? I don’t think it’s ever going to trend in anything more than the goth and metal community, but black, white and even greys never go out of style. They’re classic, timeless and impeccable. They bring an air of culture, style and enhance ANY wardrobe.

    • Barron on

      I wouldn’t / didn’t imply it was trendy, simply a color to incorporate if you’ve shied away from it in the past (as I have). But yes I agree, colors in general never go out of style necessarily, and black / white / grey especially have a place in practically any wardrobe.

  9. Derek on

    I don’t tend to go all black with too much, but I do love textured greys, charcoals, and blacks. Especially in the winter.

  10. Cameron Stewart Olson on

    I’m not much of a black guy either, but I do have some pieces that I like especially for going out – one of which is a sharp pinstriped button-front. I’m pretty picky about wearing black, since the vibe here is a lot more earthy. But I agree some black pieces round out a wardrobe nicely. Mixing greys and pops of white make a black outfit a lot more interesting, too. I’d like to get a pair of the Jack Purcell’s, or Frye’s Greene Low Lace.

    As for workout clothes, I’ve been going monochrome. It’s simpler, it’s efficient, and I don’t have to worry about looking like Easter vomited my outfit.

  11. Jan on

    I usually wear black when I am teaching ballroom dance classes. Put on a grey striped tie, and you look the man!


  12. mickey2942 on

    Missed the most essential black wardrobe items:
    1. Black leather jacket
    2. Black cashmere scarf
    3. Black wool coat
    4. Dressy black t-shirt