Your Guide to Kentucky Derby Hats!


Even if you have no plans to attend the Kentucky Derby this year, there are no excuses for not riding this fashion trend year-round.  Hats are functional, stylish…. and can go a long way toward hiding a bad hair (or no hair) day. Still, depending on the occasion and the wearer, some chapeaus are likely to evoke more scorn than admiration (e.g., wearing a fez at any gathering other than that of a fraternal organization.) Here are a few of my favorites, with caveats listed for each.

Animation Minneapolis
FEDORA modeled by James Roy

CHARACTERISTICS:
Full, round brim, creased at the top, generally made of felt. Often associated with prohibition-era gangsters of the 1920’s.

HOW TO WEAR:
Lends an air of class and authority. On men, requires plenty of confidence, collared shirt and/or suit jacket. Women can pair fedoras with virtually anything from denim to dresses, conveying an “act like a woman, think like a man attitude.”CAVEAT:Recent fedora-shaming campaigns have made this an unpopular choice with men. (See Facebook page “ Take That Fedora Off You Look Like a Tool.“) While Derby appropriate, use caution when wearing  around less sophisticated crowds – particularly if sporting a soul patch.
Animation Minneapolis
BOWLER modeled by Todd Isaacs

CHARACTERISTICS:
Bulbous, sturdy wool-felt body with short, rolled brim.

HOW TO WEAR:
Commonly reserved for eccentrics, the key to wearing a bowler is to act nonchalant about it as if you just threw it on your head and forgot about it.  Can appear to be the finishing touch on formal attire – or cross the line into costume territory if not careful. Casts a slightly sexy, boyish charm on women.CAVEAT:
Do not under any circumstance wear a bowler if you have a round face – particularly if it’s green and sporting a shamrock.
Animation Minneapolis
CLOCHE modeled by Anna Fleissner

CHARACTERISTICS:
French for “bell,” a cloche is a fitted hat that covers a woman’s head from just above the eyebrows to the back of the neck.

HOW TO WEAR:
Adds touch of femininity when dressed up or down. For added detail, embellish with flowers or feathers.

CAVEAT:Almost certain to give you irreversible hat hair. Fortunately, due to the small scale of the hat, it’s considered perfectly acceptable to wear to a restaurant or other indoor festivities.
Animation Minneapolis
PORKPIEmodeled by Eric Riggs

CHARACTERISTICS:
Cylindrical crown with a flat top – think Walter White in “Breaking Bad.”  Most often made from felt fabric or straw.  Name stems from a traditional British pie.

HOW TO WEAR:
A stand out look when paired with casual or dressy attire. Because of its smaller stature, pair with slim clothing – think short sleeved button-ups and chinos (men). Women should avoid anything too loose-fitting.

CAVEAT:
Avoid wearing with a hazmat suit.
Animation Minneapolis
SUN HAT modeled by Allison Howle

CHARACTERISTICS:
This hat, designed to shade the face and shoulders from the sun, is typically made from  straw, cotton or other woven material.

HOW TO WEAR:
More appropriate for the beach than Churchhill Downs.

CAVEAT:
Skip the chin strap lest crossing over into geriatric territory.
Animation Minneapolis
WESTERN HAT modeled by Brian Thompson

CHARACTERISTICS:
High-crown, wide brimmed hat usually made of felt or straw. Often adorned with a decorative band. Originally functioned as protection against weather for cowboys.

HOW TO WEAR:
Opinions vary widely on this one, though I’m of the camp that believes you should only wear a western hat if you’ve spent some time in the saddle.

CAVEAT:
If you haven’t technically earned your spurs but still have a lot of attitude, feel free to take a gamble on this one if you embody at least 3 out of the following 5 qualities: Soft eyes and heart – hard everywhere else, Look good in a pair of jeans, Strong enough to wrestle cattle – tender enough to caress a baby, Always opens the door for a lady, Love of animals and the land.
Animation Minneapolis
DERBY HAT modeled by Heidi Habben

CHARACTERISTICS:
Definitions vary according to gender.
A) For men, another name for the bowler.
B) For women, colorful, sometimes tasteful but more often big, bold and over-embellished with feathers, flowers and elaborate ribbon configurations.

HOW TO WEAR:
Best to choose your hat first – then style your dress accordingly (read simply.)

CAVEAT:
When it comes to Derby Hats, go big or go home. Who really cares about the ponies, anyway?
Animation Minneapolis
TRUCKER HAT modeled by Matthew Kroese

CHARACTERISTICS:
These bigger uglier versions of a baseball cap feature a higher flatter front with a mesh back. Originated as free, promotional give-aways from feed or farming supply companies to farmers, truck drivers or other rural worker

HOW TO WEAR:
As long as you’re wearin’ it loud and proud, complete with a marquee-sized logo front ‘n center, this look can be dressed up or down. But then again, I am from southern Minnesota.

CAVEAT:
While some view the trucker hat as one of the most regrettable fashion trends to ever go mainstream (right up there with Livestrong bracelets), I’m of the viewpoint that trendworthy or not, certain individuals are genetically predisposed to wearing trucker hats, and should be allowed to do so free from onlooker disdain.
Animation Minneapolis
FASCINATOR modeled by Kara Wayne

CHARACTERISTICS:
Headpiece that affixes to the front or side of the head with a clip, comb or headband. Often made from ribbons, flowers  or feathers. Best when worn slightly angled over one eyebrow, imparting a “fascinating” look to the wearer.

HOW TO WEAR:
Most appropriate for a wedding, garden party, art opening or  — the Kentucky Derby.  Avoid wearing in situations where  you will disrupt the vision of others, i.e.,  a movie theater or symphony.

CAVEAT:
Learn a lesson from Princess  Beatrice, whose fascinator  (some say it resembled a toilet bowl festooned with ribbon) at the 2011 Royal Wedding of William and Kate nearly brought  down  the monarchy.  Too much is simply…. well, too much.
Here’s hoping this year your hat helps you bring home the “purse!”

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