Buy one size up and it will fit well.

Im 5'8 with a 30-31 inch waist. Would medium be okay?

According to the size chart provided by Shock Doctor, the Medium is best suited for a waist size of 32"-34" and the small is 30"-32". Based on your measurements the small would be the recommended size.

I tried to wear these for baseball and the cup just sticks out to much compared to other jocks. Why is this??

They designed the size of the cup much larger to make it comfortable for the wearer.....you need to replace the cup with smaller size or get a different brand. All Shock Doctor cups are pretty large.

Age Range	Adult
Color	White
Size	XL
Hand Orientation	X-Large
Style	Adult
Material Composition	100% Mixed
Height	1 inches
Length	5 inches
Weight	0.5 Pounds
Width	3 inches
Material Type	Blend
Number of Items	1
Number of Pieces	2
Outer Material	100% Mixed
Season	Spring-Summer
Skill Level	competitive
Features	Breathable,Stretch
Sport	Multi-Sport
Included Components	1 jock strap with cup
Batteries Included?	No
Brand	Shock Doctor
Department	mens
Manufacturer	Shock Doctor
Item model number	213-02-35
Product Dimensions	12.7 x 7.62 x 2.54 cm; 1 g
ASIN	B00181ET1Q

Shock DoctorJock Straps for Boys with Cup Included, Cups for Football Baseball. Core Protective Athletic Supporters for Youth.

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