The Playbook

Back to School Wardrobe

From shopping circulars to The New York Times, back-to-school wardrobe guides are a dime a dozen. Between product placements and a criminal overuse of the word “timeless”, many of the aforementioned guides do little to guide your thinking. Instead of advice for dressing well, they promise you a “cheap, versatile, basic wardrobe” – in other words, a one-time solution. So for the very first style entry of THE PLAYBOOK, we thought we’d do something a little different.


It’s the classic “give a man a fish” scenario. Whether it’s a button-up or a fishing rod, why dictate when encouraging growth is ultimately better? In my opinion, design legend Charles Eames said it best: his goal as a provider was always to create solutions that provided “the best, for the most, for the least.” There’s simply no way to do that without teaching.

With Eames’ motto as lodestar, I sat down to build a versatile two-week budget wardrobe by thinking through how it’s typically done – the 100-tab Chrome sessions, the microscopic price comparisons, all of it. Approaching with that process firmly in mind, I then did the opposite.


For one, maximization behavior applied to savings on already-cheap clothes creates some serious ethical dilemmas. Below a certain threshold (~$30 shirts, $15 tees, $30 jeans), I just can’t conscionably recommend buying an item. Those prices cover cost of materials and the expenses related to running a global supply chain, but just barely. Any full-price item stickered below those prices is likely the result of cut corners somewhere around the world – you hope it’s just from the use of sub-standard materials, but it’s likely from something much less humane (see: The True Cost (2015)). Besides: you just admitted your best-case scenario was buying an inferior product. When the difference between good and bad costs less than a cold brew, why risk the torn pants?


And for two, focusing on product comparisons alone is pennywise but pound-foolish: if you don’t know why clothes look good together, the wardrobe I suggest will exist in isolation without providing the style foundations you were searching for. Again: we’re here to build a cohesive but flexible collection of clothes. Buying a concert tee on Saturday then wearing it on Monday would throw off that product-obsessed foundationless system, and that’s the exact opposite of versatile.

Those considerations in mind, a new goal emerged: to build both style fundamentals and a complete two-week wardrobe for the least money within reason. Even better, to shape a learning process that’s as smart and simple as the wardrobe it will create.

Three weeks, two neighborhoods, and a trip to the tailor’s later, the results are in. Here’s how to build a versatile, adaptable, laundry-twice-a-month wardrobe in three simple steps. 


Step One: Assess Your Needs


If you sought out and are currently reading a “back-to-school wardrobe” guide, I’m going to make the assumption that you’re somewhere between the ages of 16-28, spending most of your day in casual dress. Some schools do still require classroom dress codes, but fear not: the wardrobe we’re building is the sort of “smart casual” that makes an impact everywhere. Whether you spend tonight hitting the books or hitting the town, you’ll be ready.

With this “polished” look in mind, we’ll be focusing on solid color casual basics – things like cotton crewneck tees, oxford cloth button-ups, indigo denim jeans, and white minimalist sneakers. Not only are these choices good-looking and meant for combination, but they’re also transitional: an oxford button-up is accepted in both offices and sports bars alike. Ditto for the white sneakers. Some limits do exist (ex. don’t wear a t-shirt to your Law School interview), but thanks to fashion trends and societal changes alike, the wardrobe we’re building has more crossover than Steph Curry in a Venn diagram. Sound good? Then let’s begin.

After hours of research and more fitting rooms than I could count, I landed at Uniqlo’s Fifth Avenue flagship store. From my experience, Uniqlo has far and away the best clothes in the budget fashion category. 

Earlier that day, I tried on selections from every one of Uniqlo’s competitors with a New York City store (H&M, Zara, Topshop, etc) only to be disappointed by either fit or build quality. I encountered neither of those at Uniqlo. I chose 2 oxford cloth button-ups, 2 tees, 3 pairs of chino pants, 1 oversized flannel, and 1 pair of selvedge denim jeans. Total cost: $235.


Step Two: Think in Colors


Color is a double-edged sword. On one hand, it’s the simplest form of self-expression. You quite literally wear your emotions, authentically reflecting how you feel to the world at large. No one is arguing against this.

But on the other hand, buying one of every color is 1) expensive and 2) needlessly complex. Building a versatile back-to-school wardrobe on a budget means maximizing flexibility, and a bright purple tee just doesn’t mesh with as many pants/shoes combinations as, say, a deep navy tee. Against olive chinos and tan shoes, that vibrant purple just looks out of place – almost like it doesn’t belong with the rest of the group. While most can only react to cases of discordant colors, you can actively prevent these disharmonies with a simple understanding of color palettes.

A palette is defined as “any similar set of elements or qualities, such as musical notes, used in a medium, in a composition, or by an artist.” Therefore, a color palette is a set of related colors presented together across the same medium. Building a versatile budget wardrobe can also be thought of as selecting items that create as many good-looking, well-fitting color palettes as possible. Focusing too narrowly means you’ll do laundry every week because you spilled beer on the only pants that go with this shirt; straying too broad means you walked out with half the store. Again: “the best, for the most, for the least.” 

With this balance in mind, I selected versatile solid-color neutrals, accented by a heritage buffalo check flannel. These choices are layering-friendly, complement each other, and most importantly, create a wide range of color combinations.


Step Three: Respect the Fit


How your clothing fits is the single most important element of dressing well. If you take nothing else away from this article, let it be this: fit over everything. No matter what you wear, no matter who you wear, you will be judged first by how it fits. In the past, clothes were produced made-to-order and tailored for the needs of individual customers. Getting clothes custom-made costs dramatically more money and time than buying “off the rack”, but ensures that every part of your outfit, well, fits. As late as the end of the 20th century, most Americans – from Oklahoma to Park Avenue - had their clothes made by a local tailor. More on tailoring later.


In the present, however, we’ve traded precision for production: clothing is mass-produced and made to fit a spattering of shapes determined by population average measurements, not by people. Unless you’re a spot-on 5’9”, 196lb American male (one of 2.4 kids, making $24,062 per year), the clothing you buy is designed not to fit.


So what do we mean when we talk about “fit”? For starters, we don’t mean “tapered”, “slim”, or any other word that just means “noticeably tight.” Rather, fit is defined by how well your body matches the dimensions of an item of clothing (e.g. a garment). A well-fitted garment complements your body shape and is not deformed in any way by you wearing it. If fabric is bunched or seams don’t sit flat, try a size larger. If fabric is “pooling”, go one size down. Regardless, the off-the-rack garment should complement your proportions as they are. However: if you have to err, you should always size up. Half-size big is infinitely more acceptable than “dude don’t tell me that’s a vein.”



Seems like a lot of work to get a shirt, right? You’re not wrong. This “least worst” juggling game is a uniquely modern phenomenon, and one of the many trade-offs a consumer can make in pursuit of lower and lower prices. Unfortunately, thanks to the siren song of savings maximization, garment fit is sacrificed more often than not. That’s not to draw a false dichotomy between saving money and looking your best in well-fitting clothes: cheap garments can be made to fit just as well as any others if you know where to go. 


After trying on the new clothes around my place in SoHo, I took my Uniqlo bag over to Nelson Tailor Shop on Rivington St, Lower East Side. Each shirt had the sides taken in, the length altered, and the arms tapered to fit my individual measurements. Because I erred on the side of “too big,” there was room to adjust these dimensions. Four dozen pins and one week later, Nelson’s had fitted all of the shirts and even tapered the jeans for just $63, bringing the total cost to a mere $298. As for the importance of great fit vs good fit: the work speaks for itself. 



For a hair under $300, I had two weeks’ worth of versatile, well-fitted, smart casual clothes quite literally tailored to my needs. From then, it was as simple as choosing shoes and a few optional accessories to round it all out.


To complete the polished transitional look, I chose a. white leather Royale sneakers, b. khaki Rosen running shoes ($49), and c. oxblood suede Royale Chukka boots ($169).



Shoes were far and away the biggest expense for a reason: they come between you and the ground. If I have to pinch pennies anywhere, it won’t be on the only material protecting me from NYC sidewalks. And with these specific three pairs (one dressy; one casual; one in-between; all gorgeous), both you – and your toesies – will be covered for whatever life throws your way. That’s a big +1 to “versatile.”


As for accessories, I chose a Timex Easy Reader watch ($29) and a pair of Club-style sunglasses ($20-200+). Even in the age of smartphones, I’m a firm believer that every grown man should own a wristwatch. Timex’s Easy Reader is as beautiful and reliable a budget watch as they come – it was the first watch I ever bought with aesthetics in mind, and after 4 years and a $10 strap replacement during year 3, it is as accurate as it is beautiful.



My sunglasses recommendation is a little more variable, due entirely to the stiff competition within the eyewear market. If you have the $150+ for Ray-Ban Clubmasters, you will not be disappointed – my pair functions great and looks even better. However, if the rest of the wardrobe has left you dangerously close to your bottom line, that aforementioned competition means that similar styles are available from startup eyewear brands without the brand cachet to charge three figures. My personal recommendations for budget Club-style sunglasses include ASOS ($20), Jeepers Peepers ($40), and Kent Wang’s “Keyhole” design ($55).



There you have it: a polished, versatile, back-to-school wardrobe, and the knowledge to use it. Instead of showering you with product placement, we walked you through the process of building – and thinking about – how to dress well, with the end goal of encouraging your personal style growth through learning. Even better: unlike your actual classes, this has no final exam. Now go on out there and ace your look.