Wearing Logos

Logoed apparel is for sale at many, many places. Total avoidance is neither easy nor necessary. Logos can easily convey greed or immaturity (since most young males wear logos) and too often are visually unattractive. On the other hand, a logo can add visual interest to an otherwise solid-colored shirt and say something about the wearer more clearly and concisely than other visuals can (for example, Polo Ralph Lauren or the Sean John brand name). It can also help make it easier to not put on a pullover backwards or inside out. (That is kind of a joke.)

A few notes first:
Advice about logos herein also mostly applies to non-logo writing on apparel.
Occasionally a small logo can be safely removed from a brand-new shirt by a tailor.
This article is aimed at men over age 21, for males younger than that often can get away with loud logos.
So-called urban culture generally is more accepting of logos, but errors still can happen.

General guidance
The most important guideline is to avoid any logo that is distracting. On any item, the brand name in large text is almost inherently obnoxious (If one gravitates toward loud logos, perhaps the hunger instead could be satisfied by bold patterns or powerful color choices.)

A visible logo is never okay for formal wear (e.g., a typical job interview or cocktail party).

Assuming both are tasteful and equally attention-getting, a symbol without text is more formal than a logo with text.
The brand name is most likely to look tasteful when it clearly is not a verb or adjective.
The brand name of a company mainly known for jeans or footwear should not be clearly displayed on any other item, for it usually raises issues of propriety and quality. If one chooses to wear such an item anyway, its formality is nearly always too low for a typical office.
Anything closely linked to entertainment (e.g., a jokey slogan or cartoon character) is very casual and not for a normal workplace or a date (unless it involves a concert).
A logo with significant sportswear or possibly controversial connotations (e.g., a political message or a brand that sells alcohol) is not suitable for most situations. Please note that footwear gets more leeway than clothing re athletic associations and by itself the "Polo" logo from Ralph Lauren is acceptable, even though it refers to a sport.
An alma mater logo is okay at some sporting events and for some lounging events (such as school reunions and BBQ) and is unacceptable for non-school work environments.
If a designer logo receives positive attention in the workplace, that can still be a bad thing, as a distraction. Also, one should avoid brand logos that might convey a sense that he is better than his co-workers. On the other hand, any famous low-end logo should be avoided (e.g., Buckle). Furthermore, one should not be the only employee among co-workers and superiors who wears logos.
Simultaneously wearing multiple logos from high-fashion labels (one or more brands thereof) is not tasteful (though a very subtle logo on footwear might not count).
Visible brand names generate curiosity - that might not be worthwhile. Young men sometimes will ridicule their peers for the brand names they wear.
To avoid confusion in business circumstances, the only shirt logo worn with business clients or the general public should be that of the employer. Meanwhile, the logo of an employer is never okay outside a work situation.
As a guest or newcomer at a private club, a shirt logo is not a good idea.
A flag or other national symbol on apparel is not normally proper for someone without a military background, and even military personnel have restrictions on wearing their official clothing.
Vacations can be fun, but the name of a place does not belong on apparel outside that environment. Neither does the name of one's country, outside of things like political events and sporting competitions.
A faded logo is almost never acceptable on a button-down shirt or jacket, unless the look is deliberately vintage.
Except maybe at a concert or other fan event, a human face, smiley face or dollar sign should not be present within a logo. A skull only perhaps on a motorcycle jacket. Wings on clothing tend to look juvenile or raise associations with uniforms (hats also for that). Just a number (with or without a graphic) is not okay on any non-sportswear apparel. A shirt's logo should not be related to a motor vehicle. A logo on the arm of a garment is impermissible beyond sportswear, riding gear, and maybe a younger man's casual outerwear, and a logo does not belong on a leg.
Acceptable is a logo less than an inch tall (with just a word or two) on one side of the chest that is hard to see from more than a few feet away. However, it should not resemble a badge or a nametag.
No shirt or jacket should have two non-tiny logos opposite or above each other; that would be distracting visual clutter.
Early in the dating process, anything more than a subtle logo near the chest or on the tag of jeans is an unnecessary risk. Some designer logos only impress women who like designer brands or are quite materialistic and can come across as arrogant to others (e.g., Hermes). Also, a fake item with fake logo is one of the worst style mistakes someone can make
A patterned shirt sometimes can accommodate a small logo near the waist if it blends into the background. A logo near the waistline must be very hard to see, and such an item should not be worn with dressy apparel.
No logo or writing should extend across the front of a button-front shirt, sweater, or almost any type of jacket. (Or the backs thereof, with a few exceptions noted later.) A logo within a circle or other non-rectangular shape is too casual for almost any button-front shirt.

Shirts (specifically)

No shirt that isn't part of a uniform should have a easy-to-see logo on its back, which is the antithesis of a serious-minded adult. The only vaguely permissible use of a logo there is on the upper back on a tiny label (preferably without text). Such a shirt (more likely a sweater) should not be worn to work or an important social outing such as a date.
A patterned shirt sometimes can accommodate a small logo near the waist if it blends into the background. A logo near the waistline must be very hard to see, and such an item should not be worn with dressy apparel.
A pure text logo on an otherwise pure white or light gray tee shirt typically makes the look very youthful and cheap.
While usually an unlayered t-shirt with a logo is too juvenile for the typical man older than 25, a near-inch circle logo on the right or left side of a tee shirt can be okay (if not as loud as a bull's eye and without a slogan). A tee shirt with a layer over much of it is rarely acceptable in a man over age 40.
A logo on a solid white or gray polo shirt often looks cheap, especially if the fit is not good. When branded, some otherwise sold-colored polo shirts in orange, black, and shades of blue and red are associated with work uniforms, especially if paired with non-denim pants in solid colors such as beige and black.
A logo on a henley should be tiny and any text almost unreadable, for the garment already is quite casual without that.
There can be a very small symbol on a sweater, but little or no text; otherwise, it is probably in poor taste or (if V-neck in solid light gray or beige) a de facto sweatshirt.

Outerwear

It is generally okay if the jacket has a small (1 inch) logo with little or no text on one side of the chest. If the brand name has prestige (a la The North Face), it can be a bit larger. Large lettering is only okay as a team or club member and perhaps security jobs or riding motorcycles. Only in such cases is it okay for the back of outerwear to have a very visible logo. A small (1/2 inch) text logo on the upper back is permissible for a casual jacket; again, if the brand name has prestige, it can be slightly bigger. A jacket embroidered with a name (or initials) is best left to an athlete's uniform.

Suit jackets/sport jackets

Though a label might be stitched on (probably the sleeve), it should be removed, no matter how prestigious the brand name is. Otherwise, that looks both clueless and tacky.

Jeans/pants/shorts

A logo (often a symbol) on the seat of jeans should be neutral-colored, low-contrast, and any text therein should be hard to see from a distance.
A small logo on the top part of a jeans or casual pants rear pocket might be okay.(Recognizable designs, such as a series of curved lines, are not true logos.)
A logo or frankly any writing on the item means de facto athletic shorts.

Watches

Outside of sportswear, the watch brand name (if any) usually should be within its face. There are a few high-end brands with hard-to-see logos on the bezel (the ring around the face) that can be worn in most situations. On the bezel, the logo should only be the brand name. Additional words reduce formality, usually to a sports watch level. (Of course with all but the most formal watches, it is okay to have numbers on the dial.) If the watch has a sporty brand name, it is best not worn in an office.

Gloves

A non-tiny logo means the pair is meant for a sporting activity.

Belts

One or two small letters in a low-contrast color or tiny (less than 1/2 inch) text might be tolerable; anything more is an attention-seeking groin. One should think twice about wearing a belt with a designer logo (e.g., the Hermes H) in the work environment, especially around clients and the general public.

Hats

A small symbol or a few small neutral-colored letters (less than an inch high) that are hard to see from a distance might be okay for casual use; if the logo is in back, it might make the hat look like it is on backwards. Beyond that, a logo or text virtually never adds anything positive.

Bags

One with an obvious logo is only for athletic-related usage, unless it is prestigious, whereupon a moderate-sized version might be acceptable in some settings.

Socks

A logo should never be visible in non-athletic usage.

Footwear

Almost anything goes re athletic sneakers, but their utility should be limited. So-called lifestyle or athleisure sneakers with the logo on the tongue or at the heel or a very small text logo on the side can be acceptable for many situations, albeit seldom business casual and never more formal. On casual shoes, any logo should be low-contrast, its text should be hard to see from a distance, and the logo as a whole should not draw attention away from the upper body and face. Nothing with a logo can be used as a dress shoe.

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