Fashion is Architecture: Navigating Men’s Clothing

Clothes make the man.  Naked people have little or no influence on society. ~Mark Twain

Table of Contents

  1. Introduction
  2. Take It All Off: Your Body Type
  3. Take a Moment to Think (Really Think) About Your Personal Style
  4. Beginners Vocabulary: And Now, Some Autopsies!
    • Autopsy of a Shirt
    • Autopsy of Trousers
    • Autopsy of a Suit Jacket
  5. Quick and Dirty Rules for Your Suits
  6. Quick and Dirty Rules for Your Jeans
  7. Just What in the Hell Do You Do With a Pocket Square, Anyway?
  8. A Note on Stores, Salespeople, and Deciding Where to Shop
  9. Resources
  10. Quickie Extra: Ten Rules of 21st-Century Business Casual (Ben Tobar, Esquire Big Black Book 2008)
  11. Quickie Extra: The King of Fop (Descriptions of the Attire of Oscar Wilde, published by Harper’s Magazine, August 2009 Issue)


I do not envy men. While I can slip on any one of the dozens of dresses in my closet for business or pleasure without even having to bother with underwear or pantyhose if I choose, my husband requires a pair of pants, a carefully ironed dress shirt, a jacket, and a pocket-square, all carefully coordinated. It would be even more of a pain in the ass if he wore ties, but thankfully, he refuses on the Linda Ellerbee basis that no intelligent man starts his day by tying a little noose around his neck.
Furthermore, buying men’s clothing is an absolute hassle. My husband won’t do it without me; it’s a two-person job (three, if you count the tailor or store clerk) to buy a suit, a dress shirt, or pants. Split shirt yoke or single? Barrel or french cuff? Pointe or spread collar? French or traditional front? Fabrics of twill, herringbone, oxford, stripes, gingham – the list goes on and on. For those of you who think men have it easier: you are wrong.

And to make things even more difficult: while men are equally self-conscious about their appearance, society often pretends they are not, and therefore no one spends any time teaching them how to dress when they are young. Oh, sure – your mother probably made sure you matched, and did her best to rid your wardrobe of those t-shirts with obscenities printed on them, but for the majority of men that’s where the teaching stopped.

No one teaches men where their natural waist is, or what the proper length of an inseam is. Your mother may have tried, but I doubt very much that your eight-year old self cared – I bet the first time she tried to check the inseam on your pants, you yelled at her about how mortifying and embarrassing she was. And then, somehow, you ended up being 25 years old and having no idea how to buy anything besides underwear.

Well, darlings, never fear. A new wind is blowing, and men’s fashion is taking center stage in a way that is hasn’t in decades. Suddenly, with the advent of the term “metrosexual,” we have a whole wide sea between “frat boy” and “skate punk” in which to swim. Jeans are cool, but so are sports jackets. Pocket squares and cuff links are back. Loafers are no longer the shoes worn by old doctors while attending the country club’s annual picnic jamboree.

Great, fine, lovely – but where in the hell do you start?

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Take It All Off: Your Body Type

Antonio over at The Art of Manliness has an excellent and detailed article on figuring out your body-type and what possible pitfalls many accompany it.

Your body type is where you absolutely must begin. Think of it as an elimination process: “ALL POSSIBLE CLOTHES IN THE WORLD” may be a scary thought, but if you begin by thinking within your body type, you eliminate two-thirds of those clothes and are left with a much more manageable portion that is right for you.

Take a Moment to Think (Really Think) About Your Personal Style

One of the best tools I use to unstump men who just can’t nail down their personal style is “What kind of a bag do you carry?”

If the answer is a briefcase during the week and a gorgeous leather carry-all on weekends, try your hand first at classic and traditional styles. These keywords translate into high-quality, simple clothing. You’ll want to focus on staples – like Southerners preparing for an ice-storm by stocking up on bread and milk, you’ll want clothes that don’t need to change from year to year. Solids, delicate chalk stripes, wool, and cotton are your friends. Jackets are straight, lapels are wider, shoulders are natural-looking and arm holes are low. A center-vent in the back of the jacket is a must. Dress it up with luxurious ties and pocket squares.

If the answer is a messenger bag or a newsboy bag, you’re probably going to want a more modern warbrobe than your Ivy League contemporaries. You’re may want a jacket that emphasizes your silhouette, and is more closely fit. You’ll probably want a narrower lapel and side vents. You’ll probably want to examine some hip details – ticket pockets, kissing or novelty buttons, a couple of sports coats that can be paired with both casual and upscale clothing.

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Beginners Vocabulary: And Now, Some Autopsies!

The diagrams below explain the basic vocabulary behind buying a suit jacket, trousers, and a dress shirt. I’m going to let them speak for me and save me some typing.

Autopsy of a Man’s Dress Shirt:

Autopsy of a Man’s Trousers:

Autopsy of a Man’s Suit Jacket:

Creative Commons License
Autopsy of a Man’s Dress Shirt, Autopsy of a Man’s Trousers, and Autopsy of a Man’s Suit Jacket by Lily Beth Tempest is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 United States License.

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Quick and Dirty Rules for Your Suits

  1. Don’t carry anything in those outside pockets; it will, I swear to you, destroy the shape of the pockets both immediately (by making you look bulky around the love-handles area) and over time (by stretching or tearing the fabric). Just don’t get in the habit of it at all – that’s what your inside pockets are for, and those should really only contain the essentials: cell phone, wallet (or money clip), keys, pen.
  2. The best middle-ground I’ve found for being stylish (but not too stylish) is by choosing a subtle shirt or suit jacket with a wild lining. This will just barely let people get a glimpse of it in your collar or the cuffs of your shirts, or when you unbutton your jacket. Zagiri makes some fantastic “going out” shirts with this effect.
  3. Pay attention to those details: turn the jacket or pants inside out and check the stitching. It should all be neat, clean, and even.
  4. Invest in at least one suit with pique stitching. Pique stitching is when the stitches (like on the lapel) are visible. This lends quite a sophisticated air to a simple suit. Theory does this beautifully, and there’s no one like Rag and Bone for this kind of detail.
  5. If you’re fashion-savvy, you can probably pull off a short break in your pants (the break is where your pants actually meet your shoe). If you’re unsure, opt for a medium break, which covers just a bit of your shoe. (See trouser diagram.)
  6. This sounds like the set-up to a dirty joke, but it’s not: when buying pants, make sure you can slide your hand between your waistband and your skin without being uncomfortable; likewise, be sure you can slide two fingers between your collar of your shirt and your neck.
  7. When in doubt of your size, choose a reputable store and have them measure you. Then jot those measurements down in your notebook, your iPhone, what have you.
  8. Let. The pants. Sit. On. Your Waist. (Not your hips. You are not, nor will you ever be, Tupac Shakur.)

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Quick and Dirty Rules for Your Jeans:

  1. Tom Julian notes in his Nordstrom Guide to Men’s Style that men should own four pairs of jeans: Black, dark blue, washed, and lived-in. I tend to agree whole-heartedly.
  2. Quality, not quantity: we continue to have excellent luck with Rock and Republic and Citizens of Humanity. They age beautifully over time and they’re comfortable to wear. As a side note, if you’re ever in Los Angeles, stop by DNA Clothing Company over on West Sunset.
  3. Caring for your jeans: follow the care instructions, and err on the side of caution. Wash those babies inside out to protect them – this prevents creases and fading. Also, hold off as long as you can on washing your jeans the very first time, and then wash them with other jeans (not simply all your dark clothing). Use a mild or “dark colors” detergent. When in doubt, take them to the dry cleaner.

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Just what in the hell do you do with a pocket square, anyway?

There are about as many ways to fold pocket squares as there are men on earth. Here are three simple ones, and some reference for the more complicated ones.

When in doubt, do what my husband does: fold your non-threatening, white pocket square to make a straight line that sits a quarter-inch or so above your pocket, ala Don Draper of Mad Men. Give it a little tilt, if you’re feeling kicky.

Want something bold? The flute (also called “the puff”) is for you. This is a bold and dashing statement.

Looking for a nice middle ground? Try the dual points fold.

Creative Commons License
Pocket Square Illustrations by Lily Beth Tempest is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 United States License.

And, lastly, you want something as unique as you are? A bit more…exotic? Sam Hober (Bespoke Neckties) has some great how-to illustrations that put mine to shame.

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A note on stores, salespeople, and deciding where to shop:

I have always loved men who have loved clothes. Before I met my husband,  I had a long-term relationships with two very different men: Scott, who was intensely athletic (the only man to ever bench-press me over his head), and yet hovered close enough around my own 5’6″ height that I discarded my high-heeled shoes; and Harrison, a man that stood 6’6″ and weighed 210. Both these men adored clothes, had excellent taste, and were very particular about what they dressed their bodies in.

Then I met and married my husband, who is built, quite frankly, like a rock star; Mick Jagger, to be specific. As puts it, “the waist of a 14 year old girl.” And yet, through all three of these relationships, I have not once varied from my tried-and-true staples of clothing stores: Thomas Pink, Nordstrom, Brooks Brothers, and Barney’s have never steered us wrong, even though I’ve used them to deal with three separate men with three completely separate tastes and body types.

Like Tiffany & Co., you don’t just pay for the quality of the merchandise – you also pay for the excellent service. A sales clerk at Thomas Pink once spent two hours with just Harrison and I, trying on just shirts and pairing them with cufflinks and ties; an equally helpful clerk at Barney’s recently broke this record by spending almost three hours on just Jack and I, looking for the perfect suit. And most recently, when my father came to town and I noticed he (a) had no scarf for winter above the Mason-Dixon line, and (b) had no handkerchiefs for how much he sweated in the old steam heat buildings, I made an excuse in the middle of brunch and dashed across the street to Brooks Brothers where, breathless, I just panted “Scarf” and “Handkerchief” – in under ten minutes I was back across the street with a 6-pack of beautiful cotton handkerchiefs and a gorgeous blue plaid scarf.

Equally important, I once bought an evening gown from Nordstrom, and when trying it on the day before the event, split the side zipper. I rushed in, in a panic, and the saleswoman was mortified that they’d sold me a dress with a defective zipper – and that they didn’t have another of the dress in my size to trade me. She quickly called in the tailor, who rushed it, for free, in time for my event the next evening.

Morals of these stories: Great salespeople will:

Spend time on you and only you, yet be good enough at their job to find you just-the-right-thing quickly, and also, be mortified if they accidentally sell you a defective product and pull out all the stops to fix the situation.

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I read men’s magazines constantly, usually because women’s magazines seldom touch politics and fashion at the same time.

If you don’t feel like getting a subscription of Esquire, invest in their Big Black Book, published twice a year. These things are packed with illustrated, funny, and easy-to-digest information about fashion, entertaining, work advice, gift-giving, etc. Catch them when they come out, because trying to back-order them after they’re gone can get expensive.

I also love the Nordstrom Guide to Men’s Style – easy to navigate, easy to reference, with great illustrations of everything from fabric types to button choices. Also comes with excellent instructions for ironing, laundry, removing stains, packing properly, and figuring out your size in other countries. $20 new from Nordstrom, $6 used from ValourBooks.

John Bridges and Bryan Curtis’ A Gentleman Entertains (written for Brooks Brothers) is also an excellent reference. Maybe you’ve shelled out some cold, hard cash for a book on entertaining before, only to find out it was way too tongue-in-cheek or too vague to be useful – this is not that book. Bridges and Curtis cover everything from tail-gating to romantic dinners to holidays with the whole fam damily. Do you know what exactly to expect from “brunch,” or when you’re entertaining clients for the first time? They do. $13 new from Amazon; even cheaper used.

For those of us who love literature and not just big glossy pictures, I recommend Nicholas Antongiavanni’s The Suit: A Machiavellian Approach to Men’s Style, published by HarperCollins.

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Ten Rules of 21st-Century Business Casual, by Ben Tobar (Esquire Big Black Book 2008)

  1. Thou shalt not wear a polo shirt to work, especially an orange one.
  2. Thou shalt reduce the number of pleats in your khakis to one on each side. But only if your thighs need them.
  3. Thou shalt covet a well-cut blazer. And a well-cut blazer really needs shirt cuffs sticking out the sleeves.
  4. While you’re nice and comfortable in your khakis, the hungry-looking kid in the lean suit is getting the promotion.
  5. We have nothing against short-sleeved shirts in the workplace, per se. Just make sure you wear the matching hat while salting the fries.
  6. If you’re wearing sneakers to work, no number of big deals or killer saves will make up for the fact that you are, in fact, wearing sneakers.
  7. No logos, no mantras, and no ironic slogans. Your co-workers and clients do not need to know your team allegiances, your thoughts on the president, or your plan to drink till she’s cute.
  8. Dress every morning like you’re going to get promoted or fired. You’ll want to look your best.
  9. No one is going to trust you to take care of their money if you can’t take care of yourself.
  10. You can dress like you’re retired only when you’re actually retired. For now, you’re getting dressed for work, sonny.

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The King of Fop

From descriptions of the attire of Oscar Wilde by journalists reporting on his 1882 visit to the United States and Canada. As published in Harper’s Magazine, August 2009 Issue

  • A black felt hat of unusual proportions
  • A sealskin cap many sizes too small for him
  • A broad-brimmed white sombrero
  • A long bottle-green overcoat trimmed with fur
  • A sky-blue cravat of the sailor style
  • A morning suit of light mastic-colored tweed
  • A monster moonlight-green tie
  • A cobweb-colored velveteen coat
  • A ring with a seal of great size
  • Loose trousers of subdued tint but of very self-assertive cut
  • A mouse-colored corduroy blouse with gray worsted pantaloons
  • A velvet jacket, concerning the fit of which he should have a word with his tailor
  • A ‘Bon Silene’ rosebud in his coat lapel
  • A boutonniere, somewhat withered, made up of heliotropes, a brightly foliated daisy, and a tuberose

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  1. […] way – groom, groomsmen, and fathers. I cover three basic types of folds in my article “Fashion is Architecture: Navigating Men’s Clothing,” as well as a link and hat-tip to Sam Hober’s great how-to illustrations for many […]

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