Tip No. 1: Try On In-Store//
If you can try the boots on in-store. This allows you to try on multiple sizes and styles so you can really get a feel for which you like and that fits you the best. If you can't go to a store then order online from a retailer that allows free shipping and returns. I recommend Zappos or Nordstrom.
Tip No. 2: Size Down//
Hunter's run big, at least a half size big, so size down. I normally wear a 6 in shoes/boots and I went with a Size 5, the smallest they had. I did try on the Size 6 just to see and my foot was wiggling around and the boot shaft was really loose on me. I also have pretty small legs/calves so the smaller the size, the smaller the circumference of boot shaft. Oh and bigger the boot the taller the boot shaft. As you can tell in the photo the top of the boot hits me about 2 inches below my knee cap. I like the fit of the smaller size because it's more "skin tight", meaning I don't have a weird gap at the top of the boot. I can still wear these with leggings or jeans and it not be too tight.
Tip No. 3: If You're Petite Try the 'Tour' Style' or Kid's Sizes//
Going hand in hand with Tip No. 2, if you're petite like me go for the 'Tour' packable style. I tried on the Original style and they were just so heavy and clunky. I knew that I wouldn't be able to wear them for very long periods because my legs would get tired. Also, if you have smaller feet/calves than the Size 5, try Kid's Sizes. They have the same classic styles and colors but in smaller sizes and a whole lot less. Or if you have wider calves try the Huntress style which is specifically for wilder calved ladies.
Tip No. 4: Wear Thick Socks//
I wear thick socks with my boots just so my feet don't move around and so it takes up some of the space inside. I also do this because Hunter's are not made for warmth/snow. They're great for rain but they will not keep your feet warm if you're out in the snow. I've read that getting the boot socks help.
Tip No. 5: Glossy vs. Matte//
Nordstrom Rack had both the glossy and the matte style. I tried on both and liked the matte better. Honestly it's just a preference of which shine you like. I read that the matte gets a white fog on them due to the high quality of rubber, but it's totally normal. You can get wipes and wipe it off or leave it to add character.
Tip No. 6: Color//
I was debating between 4 different colors: red, green, black and navy. Those are also the most popular colors that I see ladies wearing. In the end I went with the black matte because I knew I would get more use out of black (black goes with everything) than the other colors. Again, it's just a preference of what color you'd wear and what color your wardrobe is made up of. I really want to get the red pair next!
Tip No. 7: Where to Buy//
You can buy Hunter's at Nordstrom or Zappos for the regular price. If you want to find them cheaper try Nordstrom Rack and I've even seen them on/at Costco. I know random that they sell them at Costco but hey you're saving a ton of money. You can also try eBay and apps like Poshmark.