How To Wear Hunter Boots and Look & Feel Cool, ft. 9 Outfits

Hunter boots are a pain to wear.

… like they look really cute, but they’re heavy.

How To Wear Hunter Boots in Summer

While most celebrities wear them at Glastonbury, clocking in at 2 pounds, they aren’t easy to wear all the time.

Let alone a city in the summer.

… but when the puddles are too deep for your Converse, Hunter rain boots become a necessity.

So let’s look at how we can wear Hunter boots in the summer and still keep cool (literally and figuratively).

How To Style Hunter Boots in Summer

In 2006, I bought my first pair of wellies — over the next 2 summers (before I left Montreal), I wore them to every music festival I went to.

Classic Hunter boots have a 16” shaft, which means they come just to the bottom of your knees… it also means that they can be a bit tricky to wear.

Rain boots outfit inspiration

Here’s the #1 thing I’ve learned about wearing these tall rain boots in the summer:

Keep Cool

The main thing about wearing Hunter boots in summer is to keep literally cool — especially since these rubber boots trap heat.

What to Wear with Rain Boots to Beat the Heat:

1- Dresses: If your dress is short enough, it’ll complement your tall Hunter boots and help keep you cool… unless you’re Dame Shirley Bassey headlining Glastonbury, then ball gowns all the way!

2- Shorts: Denim shorts (or regular shorts) will let your legs get some air while you’re lugging around in these 2lb sweat traps.

3- Jeans: Wearing jeans with Hunter boots is possible, but you really need to make sure your top is breathable — otherwise you might overheat. Also, flared jeans can work if you fold the bottoms before you put on your boots (skinny jeans still look better though).

Wellingtons outfit inspiration

TIP: If you’re wearing them to/from your office, bring an extra pair of shoes with you — wearing wellies in your office while you’re working could weigh you down, so it’s way easier just to change out of them when you get there.

… and how to keep figuratively cool?

Try vintage or vintage-looking accessories and don’t take your outfit seriously. Imperfections (that includes messy hair!) make an outfit look much more interesting.

Now for some real and really wearable outfits…

What Bottoms to Wear with Hunter Boots

Hunter Boots and Dresses Outfits

Who doesn’t love a dress with Hunter boots in the summer?

Super cute and super cool, you’ll want to wear this combination even if it isn’t raining out…

Hunter boots summer outfits

Left to Right: Skin slip dress with a G Star Jacket, Dita sunglasses, vintage earrings and a Kate Moss x Topshop bag; Kate Moss x Topshop dress with a Burberry trench coat, Celine sunglasses, In God We Trust necklace, and a vintage bag; HVN dress with a Burberry Trench Coat, Celine sunglasses, Jennifer Fisher x Goop hoops, and a Kate Moss x Longchamp bag.

Hunter Boots and Denim Shorts Outfits

Denim shorts make your outfits literally (as in actually temperature wise) cooler — while a light cotton top will also help your outfit breathe feel cooler.

I love how denim shorts and rain boots look with a trench coat, but you can totally wear any waterpoof jacket (obviously, it’s your outfit after all).

How to wear rain boots with shorts

Left to Right: Rag & Bone denim shorts with a Burberry trench coat, Celine sunglasses, A.P.C. belt, James Perse t-shirt, and a vintage bag; American Apparel black denim shorts with a Burberry trench coat, Celine sunglasses, Isabel Marant belt a Re/Done tank top, and a Kate Moss x Topshop bag; Re/Done denim shorts with a Burberry trench coat, Dita sunglasses, Rockins graphic t-shirt, and a Kate Moss x Longchamp bag.

Hunter Boots and Jeans Outfits

While the tops shown with these jeans are cotton, with a jacket, jeans, and boots, you could still over heat.

You might want to consider only wearing jeans and rain boots when it’s a slightly cooler summer day (like 23°C/73°F).

How to wear hunter boots with jeans

Left to Right: Rag & Bone skinny jeans with a G Star jacket, Dita sunglasses, vintage earrings, a Re/Done tank top, and a Kate Moss x Longchamp bag; Re/Done jeans with a Burberry trench coat, vintage earrings, James Perse t-shirt, and a vintage bag; Black Rag & Bone skinny jeans with a Burberry trench coat, an Isabel Marant x H&M belt, a James Perse t-shirt, vintage earrings, and a Chanel bag.

Hunter rain boots are a mainstay for festivals in the summer — there is no boot that can conquer mud or rain like these.

… but you can still wear them during normal summer rainy days.

If keep your top & bottoms light — your outfit will look cool and keep you cool…

Let me know in the comments if you have any questions about styling rain boots in the summer.

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