Notes from the Basement--Part 3: Serious Casual(wear)

And here it is, the long awaited casual section. I have a feeling this is going to be a little longer than I expected, so I’m just preemptively starting section 3, and will cover both high end and entry level options at the same time. For those of you who are only reading this section because this is the only relevant part, I mainly address two tiers. The first tier is a guy (with a job) that’s just starting out, and the second tier is the lesser known high end tier that quality-wise(but sometimes not price) is above the typical Gucci/Prada/Louis Vuitton/etc etc mainline stuff. That’s not to say there isn’t really great stuff available from say, Giorgio Armani Black Label and Ralph Lauren Purple (and Black) label, just that those lines are more the exception than the rule.

Section 3.1. Introduction

The original thought behind business casual was to make things easier for men, but it’s turned into a big headache (although it’s less of a hassle than womenswear). Depending on your field, business casual can either mean a sport coat, slacks and no tie, or just a long sleeve buttondown and slacks. Throw in the complication of IT/Silicon Valley (lack of) standards, and you have an enormous recipe for confusion. Section 3.2.1 to 3.2.2 are the most directly related to corporate business casual (but is equally applicable to nicer-restaurant-but-not-too-nice-or-it-looks-like-you’re-proposing, or when you want to stand out from the jeans/t-shirt masses), with 3.2.3. Polo Shirts bridging corporate casual with IT casual (which is what you can look at for weekend/Friday wear if your fall into more towards the corporate ends of things).

Section 3.2 Business Casual

Business Casual is pretty vague, but essentially refers to everything in between a suit and jeans. Generally what you’ll find is that sportcoats, buttondowns, and polo shirts all fall into the category and you’ll need to fine tune your business casual wear to fit your specific organizational culture.

A note for beginning lawyers: you have a fine line to walk, because you don’t want to fall into the faceless crowd of undressed first year associates, but you also don’t want to attract too much attention by wearing a suit every day. Look to the younger partners that will be shaping your early career and keep it in-line with them: if you want to get invited to meetings/court, wear the clothes for it: an odd jacket (sportcoat), wool slacks, and tie. You can also keep a suit/shirt/tie at the office.

Section 3.2.1 Sportcoats/Blazers = Odd Jackets

A blazer is a blue coat with metal buttons. A blue sportcoat has not-metal buttons (horn/plastic). That’s really the only difference so you’ll hear some people referring to them interchangeably. I’m just going to refer to sportcoats and blazers as “odd jackets” for here on out.

The most versatile item in your wardrobe is a blue odd jacket. It will dress up and down, from gray wool slacks to jeans. Buy a great one, preferably MTM (or bespoke). If you don’t like the default buttons, have them changed. They make all sorts of buttons that have everything from a skull and crossbones to marijuana leaf design to school crests to coat of arms, or your own custom design if you want to shell out for it. (When I get around to the references section, I’ll link to a couple of the bigger retailers that sell buttons.)

The real key to odd jackets it to make sure they don’t look like orphaned suit coats. This look is accomplished primarily in two ways. The first (and easiest) is making sure that the pants aren’t anywhere close to the same type of pattern or color. The old and reliable rule is blue goes with gray and gray goes with blue, but when you move beyond gray and blue, just take a look at yourself in the mirror, and squint a bit to see if you look suit-esque. The second, and surefire way to distinguish your odd jackets from a suit are details like those patches over the elbows (reference to the original sporting derivation), and patch pockets. The nice thing about odd jackets is that they also have their own levels of casual built in spanning corduroy, linen, cotton, and wool.

Traditionally pocket squares are not worn with odd jackets without ties, but most guys now ignore that (including me). When you do wear a pocket square, don’t match it to, well, anything. You want it to complement your shirt and/or tie. For example, the edging on the pocket square could be the same color as your shirt, or a small element of the pattern would be the same color as your shirt.

The main thing to remember is that you can wear odd jackets with jeans, corduroys, chinos, or wool coats to find the right balance of personal comfort and polished appearance.

Section 3.2.2. Wool Pants

Well made wool pants are pretty much the most comfortable pants around, and also look the most polished of your options, so I’m at a loss to why more guys don’t wear them. They vastly improve your appearance and still keep you in line with the general khaki/chinos crowd. Generally your two best pant companies are Incotex and Zarella. Since I’ve split this from the cost no object section, let me add a note that Incotex & Zarella are around the $300 point and can be regularly found at outlets for about $150-$180 before markdowns. And if that’s out of your price range, you can easily find respectable wool pants for about $30-$60 on sale.

Do ignore the whole flat front/pleated fashion “debate” and just realize that flat front pants look best on guys with flat stomachs, and pleated pants look better in general when seated. Also do realize that if you’re only a bit overweight, you can hide about 10-15 pounds with simple single-pleat pants. Otherwise, just get pleated pants.

Section 3.2.3 Polo Shirts

For polo shirts, generally the most comfortable ones are going to be a lisle or pima cotton (and will generally be better constructed as this material puts you at a pretty high price point).

Price no object: (These are not suggested unless you either exclusively wear polos, or your clothing budget can easily accommodate them. Otherwise, your money will be better spent on bespoke button downs.) John Smedley, Ralph Lauren Purple Label, Brioni, Paul Stuart, Brunello Cucinelli, Loro Piana, Avon Celli

Logoed polo shirts: Fred Perry (not the peruvian made ones, the ones made in England), Ralph Lauren Purple Label (if you can stomach that enormous horse), Brooks Brothers, (Lacoste is okay, but they're cut a little too short*),

Optionally logoed polos: Ralph Lauren custom fit (polo.com), which gives you the option of having a monogram in place of the polo horse. [Generally monograms in obvious places are tacky, but given the choice, a monogram in this case is nicer than splashing someone else’s logo here]

Inexpensive and non-logoed: J Crew

Distinguishing points of quality on the shirts are the material (lisle/pima cotton, or a fine weave pique), mother of pearl buttons (Quality varies on MOP buttons: lacoste uses MOP buttons but they're pretty cheap ones so they look plasticky).

Polo shirts are very unforgiving if you've got a little bit (or a lot) of love going on around the waist. You're better off getting a well cut button down, and rolling up the sleeves, and (this is important) tucking it in. In this case, you absolutely need to ignore the current trend for untucked shirts, because a neat waistline has a slimming effect instead of having a tent-like drape of loose cloth. You hide mass by improving the fit of your clothes, not trying to cover it with loose fitting clothes.

*A shirt that extends down past your seat will not bell/bunch up at the sides and stay neatly tucked in (and these are relatively harder to find now).

Section 3.2.4 Shoes
So what shoes to wear with all of this? It’s actually the same answer that I gave with high end suits, and will give with jeans. The best (two+ pairs) leather shoes you can afford. I’ve said it before, and will repeat myself incessantly, shoes make or break what you’re wearing. If you want a more casual look, choose a shoe with more decorations like a medallion. A more mature look than jeans/t-shirt/athletic shoes are dry jeans (see below), a short sleeve/polo shirt, and good leather (brown) shoes/chelsea boots. (As with navy suit + brown shoes, dry/raw jeans will make brown shoes pop).

Section 3.2.4 T Shirts

Let me just start with a disclaimer: I generally disapprove of spending over $40 on a t-shirt, and I’m not overly fond of graphic t-shirts (most of the designs wear people, rather than the reverse). You also reach the point of diminishing returns very rapidly when it comes to t-shirts when you go up the price scale as well.

I’m rather fond of Agnes b. (on sale). If you can deal with American Apparel’s uneven quality/sizing and questionable CEO, they do a decent t-shirt—otherwise try Alternative Apparel. Uniqlo is another alternative, as well as Graniph.

Section 3.3. Jeans

Jeans are a tricky item, as most everyone loves them (not me), and there’s a huge range of options at every price level. As with computers, you’ll find that there’s the DIY crowd that does their own fades, and the consumer crowd that buys pre-distressed denim. A good DIY fade and wrinkles will always look significantly better than the pre-distressed jeans, which are typically clumsy by comparison. Right now, Japanese denim is the best in the world, as they’ve been obsessed with recreating the early 1900s American denim, but there are a number of domestic and European companies that also turn out world class denim.

The problem with DIY fading is that it takes somewhere around 6 months to 2 years of real use and you can only occasionally wash the jeans (better not to at all). I’ll pause for the ick factor. I’m not going to go into a great deal of detail about a DIY fading process, but basically what happens is that you find the right fit/model/brand of a dry/raw denim to start with, and then wear them (yeah, complex, I know). You’ll run into a few terms during your search, and I’ll cover a couple of the important ones here:

Section 3.3.1 A few terms

Dry/raw denim is a (factory) unwashed denim that will allow you to create your own custom fade, which is much more natural and real looking than the designer denim.

Selvage/selvedge/self edge (there’s no right way to spell it), which refers to denim that has the edge of the cloth finished on the loom during the weaving process; the process is relatively costly since it requires a particular type of loom and produces less cloth than just sewing the edge of the denim to finish it. Levis signature red line came from this process, which came from Cone Mills, a major denim manufacturer, that used to distinguish denim made for different companies with different color threads.

Whiskering The natural wrinkles that occur around the crotch, and knees during the DIY fading process.

Section 3.3.2 DIY Fade Downsides

The main downsides to DIY fades aside from smell, is indigo transference (don’t sit on anything light colored, you will leave some indigo behind), and the extra strain on the denim. The brands that specialize in ultrapremium denim already make their jeans to a much higher standard than the typical 7 for all Mankind/True Religion/A&F/whatever because they know their clients are going to be putting a great deal of strain on them. Some people even go to the extra effort of starching their jeans to further speed the process, but taking shortcuts like this also increases the likelihood you will tear your jeans (which is already a risk from the DIY no-washing process). The fades and whiskering effect comes from putting a great amount of strain on the fibers, which would normally be relaxed with normal washing.

The other thing to be aware of is that jeans stretch as well. I wouldn’t go to the extreme of sizing down to compensate for stretching, but rather just realize you can just soak the jeans to return it to the default state, or turn them inside-out and put them in the dryer with a sheet of fabric softener to combat the smell.

Section 3.3.3 DIY Fades Overview

I’m not going into a great deal of detail about the DIY process, but here’s an overview. There might be an initial shrink/stretching process, which only works if the jeans are not sanforized (sanforizing is the process applied to denim that minimizes shrinkage). If you’re an athletic guy who has a slim waist and large thighs, you might find better fits by going with an unsanforized jean, warm soaking it in the tub (while you’re wearing it), and letting it air dry (again while you’re wearing it).* Generally you’ll find that an unsanforized jean will shrink somewhere around 1” to 2” in the waist and 2” to 3” for the inseam. As with most clothes now, vanity sizing comes into play, and some jeans are just cut larger or smaller to begin with.

After that initial soak for an unsanforized jean, basically all you do is wear them incessantly for the next 6 months to 2 years. Keep in mind that anything consistently in your pockets will cause fading, so keep that in mind for things like cell phones, breath mints, or cancer causing habits you should quit. To combat the smell, you can put jeans in a plastic bag and freeze them, or hang them outside to air. (Or you can just skip the whole DIY fade part and only wear them lightly. I like the look of raw denim even without the fading.)

I know this will come up, so let me just say that generally you’ll find that APC are extremely durable jeans. If your concern is durability, take a look at APCs first, and, more specifically if you want to try the DIY fade route, check out an APC New Standard first, and then you can work your way through various jeans until you find the right fit, or you may need to turn to other manufacturers from the list below. Many of the following (especially the Japanese brands) are only available through a few importers, just as a warning. Respected jeans brands (not a comprehensive list) include:

Dry/Raw Denims:
45RPM
5EP
APC
Acne
Cheap Mondays
Earnest Sewn
Flathead
Levis*
Nudie
Oni
Pure Blue
RRL
Rag & Bone
Studio D'Artisa
Sugar Cane
Warehouse

Designer Denims (that don’t suck):
AG
Citizens of Humanity
Paper Denim & Cloth (some of the softest denim around, don’t buy if you’re hard on your jeans)

*You don’t have to spend $200+ on jeans to look good, the humble $35, Levis 514 Rigid slim fit are a good option.

And that’s it for jeans. Next up will be some sort of pictures post to illustrate some of the things that I’m talking about, and then either a post on fits or accessories, and then a catchall post that addresses things that I missed/overlooked the first time, as well as a consolidated list of manufacturers/retailers.