Building a Versatile Shirt Wardrobe

Filling your closet with the essentials of a versatile shirt wardrobe can be a frustrating exercise in multitasking, and it can take years. Having a list of what you want for each category is critical so that when deals come up, you can stay focused on what you “need” instead of just jumping on every deal. Items that can be used in tons of different outfits make the return on investment higher, making the opportunity cost of buying it lower (see this post for more about how opportunity cost impacts my decision making in menswear).

However, going for maximum versatility can be boring. After all, while we all admire the starched-white-shirt-in-the-desk-drawer-of-Don-Draper lifestyle, that would be super boring. Pattern, texture, collar shape and seasonality are the four main areas where you can start to mix it up.

Solids and Patterns

Solid shirts are the most versatile shirts you can own. In the realm of classic menswear, where you want to be able to go with or without tie, there are only two colors: white and blue.

White is more formal, blue less so. Depending on what kind of work environment or lifestyle you lead will determine how many solid blue or solid white shirts you will need. For instance, I only have two white dress shirts – one with double cuffs, and one with barrel cuffs – because I wear them so infrequently. For most people, light blue is the king of versatility because you will almost never look wrong with a light blue shirt on, even with a dark suit and dark tie.

Next in versatility are vertical stripes. Small repeating patterns such as pencil stripes, university stripes, and Bengal stripes are the most versatile. Shirts that have a white ground with blue stripes are the best place to start (and are the easiest to find).


Some textures fit better in a more formal context than others. A good rule of thumb is that a smaller, denser weave is more formal than a looser, larger or coarser weave. For instance, a poplin or end-on-end will look better with a refined suit-and-tie look than will an Oxford cloth. As Derek of “Dieworkwear” says, poplins are boring. You sacrifice zero versatility but gain some measure of visual interest by going with something like an end-on-end for business shirts instead of poplin. Coarser weaves like Oxford and royal Oxford are more at home with odd jackets, and particularly so when you break out the tweeds. Which brings me to:


One of my joys is having distinct cold-weather and warm-weather clothing. I’m currently planning a trip to Scotland, and can’t wait to pull out my Donegal tweed jackets and flannel trousers to take on the trip. In shirting, so, too, can you diversify your wardrobe with seasonality. That said, when we’re talking about having a jacket on most of the time, the concept of a linen or linen-blend shirt making much of a difference in the summer heat is a bit of a stretch. I wear linen-cotton blends all year-round, as layering can warm them up in the winter (though I do not wear my heavier Oxford cloths in the summer). So when talking seasonally appropriate shirt fabrics, everything except those cloths at the fringes (pure linens or, say, peached cotton flannel) can be pretty much worn year-round, depending on how warm or cool you tend to naturally feel. 

Collar shape

If you want the most versatile collar shape, period, then just get all medium-spread collars and be done with it. They look great with a tie and without. Cutaways, button-downs, and point collars, however, is how you add back in variety. Generally, don’t go too extreme (such as huge 1970s point collars, David Beckham-esque cutaways or tiny, anemic button-downs), and you’re safe.

Button-downs are right at home with Oxford cloth (the ubiquitous, stylish and unequaled OCBD) and with a generous roll, give an insouciant feel that have enormous charm. Cutaways give a rakish vibe that generally look best on guys with a sharp jaw and slim figure (though, when worn open-collar, look great on almost anybody, in my opinion). And point collars (such as this beauty from Drake’s), are an overlooked-of-late collar style that give off a lived-in, almost working-class charm that works quite well when done right.

As you amass enough shirts to wear day-in and day-out, you can start to branch out to other interesting areas: denims and chambrays, awning stripes, linens and flannels, and of course, colors other than white and navy. But that’s a post for another time.


Know When to Dress it Down

Soon after I joined Styleforum, a member whose name I don’t recall recounted a story that went something like this: “I was invited to a grill-out and wore a RLBL sportcoat with an open-collar shirt. Some guy yelled out, telling me I was overdressed. What the heck was his problem? That guy sucked.”

For a long time, I felt exactly like him.

When I first started to learn about style and became more active on the forum, my interest in clothing bordered on obsession. I was reminiscing about those years with my brother the other night, noting, “Menswear and clothing was all I could talk about; I was probably insufferable.” His gracious reply: “You weren’t insufferable, but… you did develop a reputation.”

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Me, wearing a sportcoat to the Star Wars premiere.

Those of us whose passion for clothes lies in the tailored world can have difficulty in deciding when to dress down—and also what that actually means. It’s hard particularly because tailoring has such a long and interesting history, embodies influences from different regions of the world, and is associated with famous and well-dressed people all throughout the last two centuries. Plus, being neck deep in Apparel Arts illustrations, Duke of Windsor photos and Vox Sartoria’s blog tends to change your perception of just what dressing casual actually is. “What do you mean, ‘dress down?’ I’m wearing a pink OCBD and wool tie!” I once exclaimed at a birthday party.


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Me, in a pink OCBD and wool tie at party.

Since those heady days of excitement, I have learned a couple of valuable lessons:

First, always remember to play it cool. Have you ever met anyone who’s recently run a marathon? If you’re not sure, then you haven’t—because they’ll definitely let you know. Likewise, many who are starting off, dropping insane amounts of money on B&S deals, thrift finds, Yoox discounts, and/or every brand carried by No Man Walks Alone, are desperate to tell whoever they can about the workmanship, the design details, the barchetta pockets! But that just isn’t interesting to most people, and it can be a major turn-off for some. Learn to play it cool.

Second, I learned to be okay with not wearing a sportcoat everywhere. Primarily, the problem is the desire to express my own style: I love tailoring, it’s what makes me feel good, and so I want to wear it more often than not. Another part of the problem is that I kind of have to justify the expense of all these awesome clothes. If I’m not wearing them out and about, why do I own them? I didn’t buy them just to look at them on the hanger. 

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Me, fitting right in.

While I support both points of view wholeheartedly, I did come to realize that there were times my clothing choices were a bit precious at best, and somewhat alienating to my friends at worst. Much as we may want to wear the clothes that make us happiest all the time, we do live in the real world, and it’s possible to be overdressed. The guy wearing a sport coat to the grill-out probably did look completely out of place. Just as we all shudder at the people walking the street permanently clad in gym shorts, so too can it look out-of-place to be sporting coat and tie at a baseball game. 

The other issue at stake is how your choice of clothing affects those around you. I’ve heard enough side comments over the years from my friends to make me realize they sometimes feel underdressed next to me. Not that any of them would tell me to stop dressing how I want, but I’ve become more cognizant of how the clothes I’m wearing might make them feel. And I choose to dress things a bit down if our planned activities call for it.

With all this in mind, what’s a StyFo dude to do? Here’s my answer to how you can still dress in such a way that you feel good even when you’ve decided you should dress things down: focus on the details. Wear a nice watch that you know is high quality, but which doesn’t call undue attention to itself. Wear a navy polo with a rakish cutaway self-collar à la Agnelli. Wear your trousers that have side tabs and the extended waist closure. You can take pleasure in these small details, but they won’t call undue attention to themselves, or to you. If someone does notice them, it’s an opportunity to share a bit of what makes your clothing (and your hobby) special (but play it cool!), and thereby snatch sartorial victory from the jaws of defeat.

Versatile Shoes You Can Dress Up Or Down

I get told a lot that I am the “master” of pairing tailored jackets with jeans. I’m not sure if that’s true (people who say that probably haven’t seen @NOBD’s masterful mixing of tailoring with denim, chronicled over many years), but what I do know is that a major element of getting it right is having versatile shoes that work with both tailored and casual clothing equally well.

My footwear choices have settled into a pretty small rotation of shoes and boots that get tons of wear through regular rotation. As always, the major motivational forces behind my choices are versatility and maximizing the dollars I spend. I have settled on the shoes I own because they can be dressed up or down. So I thought I’d share with you the guiding principles I use when deciding what shoes to buy or wear. Before moving on, let me say I am not a sneaker guy, so I have no related guidance to share in this post.

First, here are some basic characteristics I look for in a shoe, with a brief explanation:

  • The less shiny, the better.
    • See this painful WAYWT post from 2011 to understand how I arrived at this point. With denim, a shiny dress shoe just looks like you changed out of your suit but forgot to bring a change of shoes.
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Kids, don’t do this.

  • The only exception to this rule is shell cordovan. I can’t explain why it works, but it does. #8 Alden tassel loafers were practically invented for selvedge denim, in my opinion.
  • Texture is good!
  • You can’t go wrong with suede, generally.

    • These two go hand-in-hand, but obviously there are textures aside from suede that can work well with denim that aren’t too rugged for tailoring. Pebble grain stands out in my mind as an excellent variation of calf leather that holds just enough surface texture for jeans. Boots in Chromexcel or other matte finishes can work with tailoring, too, but that will often depend on the overall design (e.g. Doc Martens are a no-go with tailoring, but a more classic wingtip boot might).
  • Brown, basically all the time
    • Not that this point needs to be made on Styleforum, but black is usually best reserved for more formal fits. One exception is black suede, which can look great with black jeans as well as gray trousers. The only black shoes I own are black cap-toes, which I reserve for dress wear. However, I think black suede can look awesome with charcoal or mid-gray trousers, as well as dark denim.
  • Not too pointy, not too roundy
    • Super pointy shoes look weird with denim. I think it’s because more pointed shoe lasts tend to feel refined and elegant, which clashes with the ruggedness of denim. The line between too pointy and reasonably pointy is fuzzy, though. Christian Kimber’s last shape from his collaboration with Eidos a couple winters ago had an aggressively tapered toe, but on a chukka boot with a commando sole in dark brown suede. It looked good with slim denim, but I’m not sure it would look good with a wider cut, including a 501-style silhouette. And of course, many Texans swear by pointy cowboy boots with denim (which I can fully get behind).
    • On the flip side, you can’t go too rounded in toe shape if you hope to dress them up. In my mind, a Clarks desert boot looks right at ease with chinos or jeans, but is too round for use with dressier fits, so it fails my versatility test. Somewhere in between these extremes is the range I tend to stay in.

Here are some general, holistic rules to consider:

  • Pointier, daintier, shinier shoes look good with trousers and suits, but not as good with denim or chinos. The blucher style can be dressed up or down more easily than the balmoral style, as can loafers. Thin soles with a narrow welt feel more dainty to me—though some ballsy folks have rocked Belgian loafers with denim to great effect.
  • Rounder, more rugged, more textured or suede shoes look good with denim, but weird with trousers or suits. Ankle boots like chukkas, jodhpurs or chelseas can work with dress trousers as well as denim, but that look does best when the hem is on the shorter side so they don’t have too much of a break. The same goes for higher boots. For both types of boots, just make sure the last shape “toes” the line (heh, get it?) between too pointy or too rounded.

Finally, here are some personal notes that build on the above points:

  • Did I mention that suede looks good with nearly everything?
    • Dark brown or snuff suede is universally attractive and will never look bad. At this point, I pretty much only wear suede dress shoes. Penny and tassel loafers see wear most of the year round, with chukkas and jodhpurs added in the colder months. I only wear my calf double monks and black cap-toes every couple weeks or so.
  • Pebble grain calf leather is the next best thing to suede for dressing up or down.
    • I’ve been eyeing some pebble grain tassel loafers, and am perennially attracted to Scotch grain long wings. 
  • It’s good to have a pair of ankle boots or pebble grain shoes with rubber soles.
    • Boots with a Dainite, commando, or other rubber sole are a must for rain and wintry slush.
  • There is one other pair of shoes I own that gets more wear than all the rest of them combined, but which I don’t generally wear with tailoring: the canoe moccasin. It’s a far more casual shoe, and something I wear with shirt jackets, sweaters, or just with my shirt sleeves rolled up. Mine are beat-to-death Sperry’s that I suspect may be some of the Chinese knock-offs that are sold through Amazon. My favorite well-made ones are the Oak Street version, and I intend to get some of those at some point. On the other hand, it’s kind of refreshing that a two-year old, $20 purchase is still going strong and providing me with so much use.

What are your criteria for footwear that is versatile enough to dress up and down? Sound off in the comments!

Making Smart Menswear Purchases

In my last post, I talked about developing a capsule wardrobe. The concept behind a capsule wardrobe is that you have a small collection of stylish basics that all — or mostly all — work together. However, some of us aren’t driven by a need for simplicity. We don’t really need or want to wear a uniform, nor do we need the comfort that comes knowing that any combination of what’s in our closet will look good. Some of us just like clothes and want to look cool when we are seen by other people. This week, I’ll discuss building a versatile wardrobe by making smart menswear purchases – and more specifically, how to know whether to make those purchases.  

Popping tags is fun, and of course the fashion industry grinds on, which makes us want something a little fresh and new every once in a while. Usually, there’s a catch: most of us don’t understand the intricacies of clothing’s historical context, nor do we have the time to read it all for ourselves — nor do we have, most of us, the closet space to house all the things we would buy if time and money were no object. 

And so we make purchases based on what we like – often either what’s new or what’s on sale. “Ooh, an extra 40% off those sweet Wallace & Barnes selvedge chinos!” UPS delivers them a few days later, and you find that they don’t quite look as good with your only pair of nice shoes – museum calf double monk straps – as you thought they would.

The best way to avoid this is to use a framework for your decision-making, one that will ideally keep you from buying garments you don’t need or won’t wear. I’m going to use the metaphor of a picture frame to describe how I make these decisions: there are four sides to a frame, and each side represents a question you can ask yourself as you look through the frame at the item you’re sweating over with credit card in hand.

Question 1: how does the garment fit, formality-wise, within the context of what I wear?

I love me some military field jackets, but generally speaking, my favorite clothing is tailored. Those two don’t fit together very well, except under specific circumstances (i.e. your tailoring is very casual, or your M65 is more of a refined homage to the field jacket instead of a literal reproduction garment). Nine times out of 10, when I go to get dressed on an evening out, I’m reaching for tailoring, not “workwear” or “streetwear.” That’s okay. Other guys rock the M65 all the time, and I admire their style – but that’s just not me.

Similarly, if you only wear tees and broken-in selvedge denim, the midnight navy shawl lapel tuxedo jacket you have your eye on probably isn’t going to give you a lot of use.

For help in understanding how to answer this question from the perspective of someone who regularly wears a jacket and tie, browse the Internet archive version of Vox’s Coherent Combinations for Beginners thread. It was eye opening for me, and it may be for you too. It can help you place your different garments where they belong contextually.

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This M65 looked awesome, but I never wore it because none of the rest of my wardrobe at the time looked good with it. So I sold it at a loss.

Question 2: is my wardrobe seasonally balanced?

In building my wardrobe, I have tried to make sure I have good clothes to wear when it’s warm or when it’s cold. It’s hard to keep parity between the seasons because, in the world of tailoring, cold weather gear is immensely more interesting (tweeds, flannel, ancient madder, suede – you know the drill) than summer clothing. I’ve had to consciously ask myself whether what I’m looking to buy fills a more immediate need in one season or the other. You don’t want to be stylish only half the year, even if there’s never been a better deal on a cashmere crewneck than during a summer sale. Try your best to build a complete wardrobe, not one that’s full of nothing but beautiful winter coats.

Question 3: if I buy this now, will I regret it if something else on my wish list is available in a month and I can’t afford it because of this purchase?

One of the major driving forces of my life is opportunity cost. I’ve found time and again that when I get emotionally invested and buy something that isn’t a “need” so much as it is a “want,” shortly thereafter I regret the purchase because something I really do need comes available. 

Take stock of the holes in your wardrobe, and know what you need. That way, when something that makes your heart beat fast comes along, you’ll be able to honestly assess whether it’s something you need and would actually get wear out of, or if it’s just the thrill of popping tags you’re after.

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I spent an inordinate sum of money in alterations to try to make this vintage tweed eBay find fit. And those expenses meant a few weeks later when I stumbled on my literal dream Eidos jacket at deep discount, I had to pass for lack of funds. It was soul-crushing. Stupid tweed jacket.

Question 4: Do I already own a similar garment?

This is the one side of the frame that stands out from the rest, because it’s how you help yourself break out of your rut: how many navy polos do you have? Do you really need another one? If you got this one, would you really wear it? On the flip side, would you neglect another perfectly good navy polo that you already own?

Now, some people wear a white shirt to work every day and need multiples of things like that (and please, for all our sakes, I hope you have multiple pairs of socks and underwear). That said, when we’re talking clothes we like and are buying for pleasure, it’s important to make sure you aren’t stuck in your ways. It’s fun to grow. Our tastes and preferences in menswear, like everything else in this life, need growth to sustain our interest. Staying rooted in your style preferences doesn’t mean wearing only the basics day in and day out. Try out those combinations you see the cool blogger-types share. Sometimes you’ll look ridiculous and other times you won’t – you have to try to know for sure.

Use this frame of decision making to help you assess your purchases. If you’re anything like me, it won’t ensure you hit home runs on every purchase, but if you can keep your wits about you in the rush of sale season, you’ll be happier – and generally better dressed – in the long run.

How to Build a Capsule Wardrobe, Pt. 1

We’ve all wondered how to build a capsule wardrobe: that ideal state where your overtly materialistic tendencies are replaced by Zen-like peace of mind; you dress how you want every day, you own only what you wear, and you are one with the Force. Nobody lives this way, but it’s a nice goal. In this two-part article, I’ll elaborate a bit on the thought processes you can take to work towards it. In part 1, we’ll focus on who you are, and what you’d like to wear.

Appraise your current wardrobe and where you are in your menswear journey.

Are you a newbie who’s just getting into clothing? That is, you’ve just come across Styleforum and are realizing that everything you know is wrong? Or have you already amassed a large wardrobe of clothing, but still find it difficult to decide what to wear?

In either case, you have much to learn, and I’m not just talking about the “rules.” I mean about yourself—your style; the version of yourself you want to project through your clothing that is most sensible for your lifestyle and life’s circumstances. If you’re just starting out, resist the urge to buy any and every awesome piece of clothing you see on B&S/eBay/deep discount. You will do yourself a great favor by just making do with your current wardrobe while you figure things out. How do you “figure things out?” You observe and participate in discussions here, and find the “Coherent Combinations for Beginners” cached Internet Archive thread from Voxsartoria.

If you’ve got an already-large wardrobe, pay attention to what you come back to time and again. Pare your closet down to what you actually wear. I alway put my most recently worn shirt to the furthest right in my closet. I almost never get more than 8-10 shirts deep before I’ve washed them and start over again with those same shirts. All the shirts to the left of that are either: 1- Seasonal shirts (madras or linen or Oxford), or 2- Shirts I don’t wear. You can probably safely get rid of the non-seasonal shirts you don’t wear except for the ones you need for special occasions. Figure out a similar system for trousers, jackets, and even shoes.

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A capsule wardrobe will free up closet space, which just feels good. And unless you have unlimited funds—and assuming what you own is quasi-valuable—you can get actual money out of these obsolete possessions. Sell them on the buying and selling forum, and use that money to upgrade what you keep.

Make a list of what you would want to make your dream capsule wardrobe. 

Making a capsule wardrobe is like packing for vacation: you need versatility, where everything goes with almost everything else. But this is more aspirational—you are picturing what you really want in order to become the best-dressed version of who you want to be. In my case, I actually created a Pinterest board with photos of cool clothes (I found out later a bunch of those pics were of @NickPollica – the Creatie Director at Eidos – before I knew who he was; go figure). I wanted to have a “complete wardrobe,” and I had a bookmarks folder with links to actual products that matched those inspirational photos.

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This step is the most important, because you’ll find all kinds of awesome stuff on sale that you’ll love and which would totally make your life better if you owned it. But your goal isn’t to buy everything that’s awesome, it’s to make a lean, wearable, flexible wardrobe. Having this list will help you when you’re three sheets to the wind and that Mt Fuji kimono is on clearance at No Man Walks Alone. You can pull it up and remind yourself of what you actually need, not just what would make you the coolest dude this weekend at Acme on Broadway in Nashville.

Having this list also helps you to upgrade what you already have systematically, piece by piece. For instance you may have a workhorse Brooks Brothers suit, but now prefer Italian tailoring. Once you know what in your wardrobe needs to be upgraded, you can start looking for the best replacements.

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