On the fence about purchasing Hunter Boots? Fall is the best time of year to invest in a pair of Hunter Rain Boots. I have seen quite a few pairs of shoes ruined on a haunted trail and with all this crazy rain we’ve been having in the Carolinas, these boots are a necessity. Looking through my blog, I have worn these Pillar Box Red Hunter Boots hands down the most of any shoes and wanted to compile all of the looks to inspire you 🙂 Hunter boots do have weird sizing issues, but never fear! I explain what to know before buying Hunter Boots here.

1. With Skirts & Sweaters: This is my favorite way to style the classic rain boots. I’m not gonna lie… I’ll do anything to keep from having to wear pants! So I layer thermal knee socks under my Hunter Boots to keep warm and comfy in the Fall.

Tres Chic Sweater

Sweater: Forever 21 (old, similar here) / Turtleneck: Old Navy / Vest: J. Crew Factory  / Skirt: The Girl That Loves c/o (only $19!) / Bag: Tory Burch / Boots: Hunter

Vest and Fair Isle Skirt

Skirt: Windsor Store c/o / Sweater: Windsor Store c/o / Vest: Lylas by Moss c/o / Boots: Hunter / Coordinates Bracelet: T’Audrey c/o / Verse Bangle: Bip and Bop c/o / Pearl Bracelet: Shop Fabulessly c/o

Hunter Boots Outfit

Sweater: Old Navy / Skirt: Forever 21 (Similar Here) / Boots: Hunter / Bag: Kate Spade / Sunglasses: Karen Walker / Necklace: Etsy / Watch: Michael Kors / Bracelets: CoachEtsyMacy’s / Rings: Gigglosophy, Sweet Caroline / Lips: Stila Beso

Creme de la Creme Sweater

Sweater: Zoe Karssen / Shirt: Michael Stars / Skirt: Delia’s (Forever 21 has a simliar version) / Boots: Hunter / Bag: Kate Spade / Clutch: Milk & Honey / Sunnies: Karen Walker / Necklace: H&M (Similar Here) / Watch: Michael Kors / Bracelets: Stella & Dot, Open Sky, Tiffany’s / Rings: BaubleBar, Sweet Caroline / Lips: Stila Beso

2. With Leggings: I love a good pair of leggings (read: I’m lazy) and I slip on my Hunter Boots to run outside and walk my dog, check the mailbox, and get safely to my car in a storm. Pair with an oversized sweater or layer with a dress and vest and you have a chic and functional outfit!

Plaid Blanket Scarf and Hunter Boots

Sweatshirt: Old Navy / Shirt: Michael Stars / Pants: Old Navy / Socks: ASOS / Boots: Hunter / Scarf: Forever 21 (similar here) / Rings: Swell Caroline, BaubleBar / Bracelets: Michael Kors, Coach, Ann Taylor, Tiffany / Lips: Stila Beso

Karen Walker Super Duper Sunglasses

Dress: H&M (Old, LOVE this one) / Sweater: Similar Here / Coat: Nasty Gal / Boots: Hunter / Sunglasses: Karen Walker / Rings: BaubleBar, Swell Caroline / Bracelets: Michael Kors, Coach, Jewelmint / Lips: Stila Beso

Kate Spade Beau Bag

Dress: Express (40% off now!) / Plaid Shirt: H&M (sold out but similar here) / Leggings: H&M / Boots: Hunter / Bag: Kate Spade / Sunnies: Karen Walker / Ring: Swell Caroline / Bracelets: Forver 21, Ann Taylor, Tiffany, BaubleBar, Michael Kors / Lips: Stila Beso

3. With Jeans: This is an obvious one. Be sure to try a few sizes and calve widths of the boots to make sure you can fit them comfortably over a pair of jeans.

Striped Vest and Red Hunter Boots

Sweater: Old Navy (old) / Plaid Shirt: Old Navy/ Vest: Amazing Lace c/o / Jeans: Juicy Couture for Kohl’s / Boots: Hunter Boots / Bag: Galian Handbags c/o

red hunter rain boots outfit

Shirt: TopShop / Vest: Nordstrom Rack / Jeans: TopShop / Boots: Hunter Boots / Bag: 3.1 Phillip Lim via Shopbop

Shop all of my favorite Hunter Rain Boots here:


6 comments on “How to Style Hunter Boots: Outfit Inspiration”

  1. Going to Scotland in July. I’m 5’3″ and wear 7 to 7 1/2 shoe size. Legs are shorter. Thinking about the matte adjust rainboot. Seem better for shorter legs. What are your thoughts!

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