According to MID Regs, 5.10

Any new hairstyle I consider I want it to be (other than being in-regs):

• Speedy (15 minutes or less from start to finish)
• Bomb-proof (I don't want it to move or have to fiddle with it at lunch to keep it in or have to re-pin it ever 30 minutes)
• Sleek (I want it to hold as much of my wisps down without too much product or ends sticking out)

As far as regs go Navy Regs/USNA regs are listed below.
NOTE: there are additional constraints if you're interested in going Marines.

Click "Read More" for MID REGS:  5.10  Personal Appearance (Women)

1. Female midshipmen shall be well groomed at all times and shall meet the following minimum standards: 

a. Hair.  Keep hair clean, neatly shaped, and arranged in a professional style.  Hairstyles shall not be outrageously multicolored or faddish to include shave portions of the scalp (other than the neckline), or have designs cut or braided into the hair.  Hair coloring must look natural and complement the individual.  Haircuts and styles shall present a balanced appearance.  Lopsided and extremely assymetrical styles are not authorized.  Pony tails, pigtails, widely spaced individual handing locks, and braids which protrude from the head, are not authorized.  When in uniform the hair may touch, but not fall below a horizontal line level with the lower edge of the back of the collar. 

These regulations will apply at all times when in uniform, including White Works and Blue and Gold Jogging Suits (BGJS).  When wearing white works or BGJS the "bottom of the collar' will be a point where the collar of a regulartion unifrom would reasonably be.  hair will be allowed to fall freely or be worn in ponytails when in PE gear.  Mishipmen are not permitted to cut other midshipmen's hair or to recieve haircuts from other midshipmen.

Multiple braids are authorized. Braided hairstyles shall be conservative and conform to the guidelines listed herein.  When a hairstyle of multiple braids is worn, braids shall be of uniform dimension, small in diameter (approx. 1/4 inch), and tightly interwoven to present a neat, professional, well groomed appearance.  Foreign material (i.e., beads, decorative items) shall not be braided into the hair.  Short hair may be braided in symmetrical fore and aft rows (corn rowing) which minimize scalp exposure.  Corn row ends shall not protrude from the head, and shall be secured only with inconspicuous rubber bands that match the color of the hair.

Appropriateness of a hairstyle shall also be judged by its appearance when headgear is worn.  All headgear shall fit snugly and comfortably around the largest part of the head without distortion or excessive gaps.  Hair shall not show from under the front of the brim of the combination hat, garrison, or command ball caps.  Hairstyles which do not allow headgear to be worn in this manner, or which interfere with the proper wear of protective masks or equipment are prohibited.

Long hair, including braids, which fall below the lower edge of the collar shall be neatly and inconspicuously fastened, pinned, or secured to the head.  No portion of the bulk of the hair as measured from the scalp will exceed approximately 2 inches.

Hair nets shall not be worn unless authorized for a specific type of duty.

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When in uniform, the hair may touch, but not fall below a horizontal line level with the lower edge of the back of the collar.

b. Hair Ornaments. Conspicuous and colorful rubberbands, combs, and pins are not authorized.  Hair rubber bands must be ari colored or clear.  When worn, hair ornaments shall not present a safety or FOD (Foreign Object Damage) hazard.    A maximum of two small barrettes/combs/clips, similar to hair color, may be used in the hair. Additional bobby pins or rubber bands matching hair color may be used to hold hair in place, if necessary.