Five Fresh Ways To Wear Tall Hunter Rainboots

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Oh, these boots. Once such a thing, and now they’ve been overblogged, over-pinned, over-grammed, and I’m totally over the whole thing.


I still have mine.  Sitting there in my hallway.  And I still wear mine, whenever it rains.  As much as I love the new chelsea-style rainboots, I can’t walk into puddles without fear the way I can with these stompers.  And when you are living in the middle of a city – with kids – you’ll be going outside everyday (alll day), regardless of the weather.

So.  Since it looks like I’ll be wearing these bad boys for the rest of my days (cue dramatic music)…I thought I’d try finding a few outfit formulas to make them feel….fresh.

But I’ll settle for moderately fresh-er.

Here are four solid options (and one hail Mary, in the spirit of full disclosure):

1. With High Rise Shorts

If I had to point to one trend that has really defined the fashion landscape of the last several years, it’s the resurgence of the high-waist.  Half-tucking any ol’ sweatshirt (or tee) into a pair of high-rise shorts instantly modernizes any outfit….even one where rainboots are involved.

Outfit Details

top: Zady Linen Sweater c/o

shorts: Levi’s Wedgie Fit Shorts in ‘Sierra Skyline’

bootsHunter ‘Tour’ Packable Rain Boots

bagSee by Chloé Joyrider Backpack


2. With a Casual Dress + Trench

I know Pinterest is filled with images of girls frolicking in party frocks and Hunter rainboots.  I KNOW.  But in my personal experience….without a camera crew, fields of flowers, and perfectly quirky accessories….it doesn’t translate.  Previous attempts at nailing that look resulted in a costume, rather than something I’d actually wear.

So here’s my Real Life Compromise (RLC? #hahajustkidding): tshirt dresses + trench coats

Trench coats are practical, something you could actually wear in the rain, and smartens things up without being overly fancy.  And tshirt dresses are almost as casual as rainboots, which makes the pairing feel natural.

Outfit Details

jacketEverlane ‘The Swing’ Trench (size XS for reference)

dressSundry V Neck Dress (a lighter blue – my brighter one here)

bootsHunter ‘Tour’ Packable Rain Boots

bagRebecca Minkoff ‘Julian’


3. With Ripped Jeans, Stripes, and Bombers

Ripped jeans look cool peeking out of rainboots.  And they keep the vibe from being overly preppy (even when paired with stripes).  Further modernize this combo with an of-the-moment bomber jacket.

Outfit Details

bomber: Free People Midnight Bomber, Navy more colors here.

teeSaint James

jeansLevi’s 721

bootsHunter ‘Tour’ Packable Rain Boots


4. With Coated Denim And Rocker Tees

This is my fav for when the rain is really coming down.  Coated denim is a little more water repellant than regular denim, and a rocker tee reinforces the tough-girl vibe.  I wear mine with an old anorak, but even a bright raincoat would be cute with this one.

Outfit Details

anorakEverlane ‘The City’ Anorak

tee: Similar

jeansPaige Edgemont Ultra Skinny Black

boots:Hunter ‘Tour’ Packable Rain Boots


5. With Denim Rompers or Dresses

Here’s my rationale:  denim is so inherently casual, and such a classic pairing with rainboots…that I thought the twist of fancy denim would elevate the rainboot look without being ridiculous.

I think it works!!

Outfit Details

jacketEverlane ‘The City’ Anorak

romper: 7 for All Mankind Denim Romper

boots:Hunter ‘Tour’ Packable Rain Boots

sunglassesRay-Ban ‘Erika’ 


Thoughts??  And if you have a go-to rainboot formula that works, shoot us a pic.  We’d love to feature some more reader style….




About Author

Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and denim-underwear, always.

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  1. Kimberly Twomey on

    This post had me laughing a bit cause rain boots are like snow boots here in CA. The thought that you would wear Hunter boots with shorts or a short dress is comical because if it rains in CA (to be honest we mostly just stay home) we wear warm socks, jeans, sweater and a heavy rain coat.

    • (I’ll preface this reply with saying I’m assuming you’re meaning Canada not California lol). I live in Canada and am totally the exception to the rule 😂 I live in the country in an area where a good foot of snow is on the ground from nov-March, yet I never wear snow boots haha (I’m weird I know!). But that being said, come spring, everything is MUD, and I just invested in my first pair of Hunter boots, so Shana, THANK YOU for this post, cause I was feeling like I couldn’t be stylish wearing them like you could a few years ago ! And I’m totally trying the dress/shorts and hunters thing !!!!!

    • Christy Hartman on

      Ha. Same here. I have cute rain boots but rarely wear them because the clunkiness just isn’t worth it if I’m just making a mad dash from my car to a door in Houston suburbia.

  2. Just google Kate Moss Hunter Boots, she rocks those boots festival style. I like 1 and 3 although I think the “denim underwear” would have looked even cooler.

  3. On trend or off they are here to stay! I live in Minneapolis and step into mine anytime it’s wet or muddy in spring summer or fall. Even if there is another shoe chosen for the day’s outfit I’m popping my Hunters on to walk the dog, take out the trash, or play in the yard with my kids. If it’s wet out I pretty much keep the pants slim or the leg bare so the Hunters look ok. Wide leg trousers are for dry days!

  4. I love Hunter rain boots. Yeah, maybe they’re currently overdone but they are so damn practical. I live in my Blundstones from September to May (okay, since I live in Canada there is an occasional wearing of snow boots but not this winter) and although Blundstones are waterproof and the most amazing shoe/boot in existence, it’s great to have a pair of rain boots that cover your legs when there’s a real downpour or you’re walking through some mucky trail or tidying up the messy garden.

  5. Bridget K Dierks on

    It has rained for literally a month here in southern Missouri (seriously, you guys have probably seen my town on the national news because everything is floating downriver). I’ve worn my hunters so regularly that at this point they’re not a style move – it’s all practicality all the time. And practical wins when the puddles are deep and you’re carrying (at least) two bags and a toddler everywhere. 🙂 Thanks for the ideas! I really like the idea of wearing them with waxed/coated denim.

  6. OMG It’s lovely to see you wearing your long Rubber Wellingtons with different outfits you look gorgeous, i slip my legs into my Wellingtons at the slightest hint of rain especially when going to work, my Nylon Stockings stay dry and there are plenty of dishy hunks only too willing to pull them off for me.

  7. Can I just say, these are the posts that I really love. Not focused around anything that’s particularly trending or in stores RIGHT NOW, not that I don’t sometimes appreciate the shopping enabling, but what I really love is when you shake the sartorial snow globe a bit and help me rethink stuff that’s in my closet, or tweak clothes just enough to make me say, huh, maybe I CAN be excited about getting dressed today. Even though it’s fifty-friggin-degrees on Memorial friggin Day Weekend, seriously what happened to May, aka, the best month in New England other than September, and WHY AM I WEARING MY MARCH/OCTOBER CLOTHES I HATE YOU GLOBAL WARMING!!!

    Anyways, more of these please & thank you, they’re great! (and maybe less bell sleeves – how the hell does anyone cook dinner in those, or is it just me? But that’s a question for a different post. . . )

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