Wearing Rainboots: Inspiration Through the Seasons (And $100 Giveaway to Bogs!)



This post is an update to our original How To Wear Rainboots – For Moms article, originally published in March of 2009.  It was in dire need of an update.  Especially since it remains as one of our top-hitting posts.  Crazy.  

When I wrote it, rainboots were being worn everywhere by celebrities and just starting to be embraced by the general population.  But rainboots still seemed a bit out-of-place unless it was actually raining.

Since then, rainboots have come into their own and are now considered a valid boot-about-town.  And while I still think they look silly on a sunny day walking down a dry sidewalk, I've amended my original "rules" (which were totally annoying anyway).

When Moms Should Wear Rain Boots

  1. When it is raining.
  2. When it is wet — meaning puddles are on the ground.
  3. When you might be wading in a stream, mud bed, or pond.

Let's just summarize things into the following statement:  Wear rainboots whenever you feel like it.  I'm going to guess that most moms will probably feel like it when it's raining, snowing, generally wet, muddy, or on a cold, gray, day.  Or during a cool summer downpour.  

What Kind of Rain Boots Moms Can Wear
[Again, from the original article]

  1. Tall plain ones – hunter green, dark gray, bright yellows, red, etc.
  2. Tall black patent leather ones — the sheen of these boots will look a little more sophisticated.
  3. Some patterns are OK for the brave — but proceed with caution on this one.  Skip the Hello Kitty boots, skip the ladybugs, skip anything with rainbows or anything that you think an 8 year old would want to borrow.  If reading this makes you nervous, stick with plain.

I'm actually OK with this advice.  But I'd also add that rainboot styles have exploded in recent years.  If you aren't a fan of the typical wellie, there are now rainboot wedges, booties, rubber motorcycle boots and, one of my personal favs, duck boots.  Here are some super-cool, non-wellie rainboots:

Screen Shot 2012-04-17 at 10.33.37 AM

Hunter Champery Wedge Rainboots |  Loeffler Randall Slip-On Rain Booties | Burberry Buckled Rainboot

Isle Jacobsen Lace-Up Rainboots |  Loeffler Randall Sliver-Wedge Rainboot | Bogs Charlot Rain Bootie


How To Wear Rain Boots?

Like our original article, I still think tall rainboots work best when worn over skinny jeans, leggings or thick tights.  Anything else tends to be bulky.  But the short rainboots?  Not only do they work with skinnies/leggings/tights, I also love them with rolled denim, making them a tad more versatile.

However, since many Mamas wear their rainboots almost year-round, rainboots can look just as fabulous paired with bare legs and dresses (or shorts) on a wet-but-warm Spring day as they do with jeans and puffer jackets in the Winter.    

Here's my rainboot / wellie inspiration board:


(photo credits, clockwise:  Momma's Gone City  | Modish Blog |  Atlantic-Pacific | Makesomething.ca | The Blond Salad)


Here's how I've been sportin' mine all through the seasons…

Wintertime sledding (this worked much better in Denver…Rainboots are NOT warm enough for Philly…)


(wearing: Land's End Puffer, Forever 21 non-maternity pants…yet they have something that looks suspeciously like a demi-panel, J. Crew hat and scarf, Hunter wellies, Target fleece wellie liners)


With a rain jacket and skinnies…ground-breaking, I know.  


(wearing: Lands End rain jacket, J.Crew scarf, Levi's denim leggings, Hunter wellies, Target fleece wellie liners, Echo Designs gloves, Salt sunnies)


Little rain booties and a cozy sweater for gray, Spring day…

(wearing: Levi denim leggings, Stylemint Perry sweater, Free People floral tank, Charlot Gum Boots c/o of Bogs)


And with a dress!  Throwing rainboots on with a dress and big sweater (or jacket) was my daily mom-i-form when we moved last May.  So. Much. Rain. In. Philly.  And yet…so warm?  But sometimes cold?  

 (wearing: Jason Wu for Target dress, Banana Republic cardigan, Hunter wellies, Target wellie liner socks)


Ready for the giveaway? 


(wearing: On S – Gap destroyed boyfriend jeans, St. James striped tee, Gucci scarf, Charlot Gum Boots c/o Bogs, On P – Target raincoat, Joe's jeans, Splasher's camo rainboots, On R – Target striped tee, Joe's jeans, Classic High Bogs, Target umbrella)

Bogs Footwear would like to offer one of our readers a $100 gift certificate!  You can choose a little something for yourself (I recommend the Charlot Gum boots – see pic above) or a little something for your kiddo (Raines has on Bogs rainboots as well).

Raines, incidentally, LOVES his Bogs.  We actually bought them this winter for sledding.  No joke.  While they are rainboots, they are comfort tested to -30 degrees (see the minus sign?  Yup.  That's MINUS 30 degrees), so they also work as winter boots.  Raines likes the fact that they are "super STRONG boots, wike..THIS STRONG" [stomp stomp stomp] for puddle-stomping.  But my fav part?  They have this easy-on handle thing…making them one of the few pairs of shoes Raines can put on/off without any help at all.  LOVE THAT.

You can enter to win the $100 gift card to Bogs Footwear by liking this post on the ANMJ FaceBook page and telling us what you're coveting at Bogsfootwear.com.

Enjoy the April showers!!


ps.  I would like some props, please, on my cartwheel.  I may or may not have hurt my wrist doing it. But it should be noted, Mamas, that I CAN STILL DO A CARTWHEEL.   And Raines thought it was awesome.  WOOT.


  1. I would definitely buy the Mckinley snow boots for my daughter…we are out in cold weather a lot and I am always looking for really great, practical products like this.

  2. That Jason Wu dress is so great. I don’t know how I missed it when the line came out! As for the original topic, I have never (EVER) owned rain boots. True story. In parched, drought ridden Texas, it’s never been an issue. With these ideas, though, I’m wishing I needed them!

  3. That pic with the 2 kiddos in their rain gear is so cute. But I wish the giveaway didn’t require fbook use.
    I haven’t had rainboots since I was a kid. Now that I live in Amsterdam, they could be useful, but I wonder if I’d rather just have some good leather boots. For those of us trying to keep our wardrobes small, is it possible to wear leather boots into the mud and puddles without wrecking them? Or should I get some cheap “play clothes” rainboots for the times when I want to get seriously mucky?

  4. Ok I need some serious rainboot help. I once bought a pair of Hunter Wellies and promptly returned them because they were huuuuuge – didn’t fit around my calves, and were super heavy to walk in. I can’t imagine chasing around my 1 and 2 year old in them, and now that I’m pregnant again I don’t want to add a ton of extra weight onto my feet!! Whenever I see pictures of people wearing them, they look like they fit so nicely around people’s calves – my calves are not super big, but I don’t think they are smaller than the people I see in these photos! What is going on? Is there a different type of rainboot I should try??
    Awesome post as always Shana – please come hang out with me in Baltimore some time!!! πŸ™‚

  5. I so need rain boots but haven’t taken the time to figure out exactly what I need. But I commute via public transportation so walking in the rain happens a lot. I think the classic high handle boots are the most practicle and they come in that pretty blue.
    It’s a rockin cartwheel.

  6. Jaime – anytime, chick!  I'd seriously love to.
    But ok – your rainboot Q.  I also have scrawny legs and the Hunter classic talls were the only ones that didn't flop around my calves.  However, if you tried the slightly shorter version of Hunters (not the booties – the slightly shorter look exactly like the classic talks but are…uh…slightly shorter – clearly I have a way with words) they are actually made for girls with a wider calf.  My hunters aren't skin tight, but decently trim.  Hmmmm….the other rainboot brands I tried were actually worse in terms of heaviness and wideness.   Let me think some more.
    Sent from my iPhone

  7. Btw, Mamas, thanks for the outfit love.  These pics are pretty much what I'm wearing, oh, 90% of the time, so you guys made my day. πŸ™‚
    Sent from my iPhone

  8. I’m totally impressed. I’ve never been able to do a cartwheel. Probably because of my complete lack of hand-eye coordination and spatial skills. lol.
    I am totally craving some rainboots, but to be honest, I am drawn to the bright patterny ones (and bright solid ones). My trench coat is bright yellow so I was thinking hot pink boots might be almost like a color blocking thing. (with dark skinny jeans and a black or dark teal t-shirt probably). I always have a tendency to go a little too Punky Brewster-eque though in my wardrobe choices…

  9. which gap distressed boyfriend jeans are you wearing? i went online and there were several to choose from. Also, some of the comments said the size was weird. what size did you get?

  10. I have to say, I got some rain boots from Kamik this winter (a black-and-white pattern, so not too over the top: http://www.zappos.com/kamik-catarina-black ) and I am LOVING them! I haven’t been bold enough to wear them when the weather isn’t wet, but I might get there. I find I like them tucked into jeans, with a skirt, or even if they’re just peeking out from underneath black slacks (which is a much less adventurous way to wear them).

  11. I’m LOVING the Jason Wu dress as well, I didn’t get my butt to Target or target.com fast enough when his line came out. πŸ™
    Can I be included in the drawing even if I don’t have a facebook account?
    I’ve been craving bogs FOREVER but have been to cheap to hand over the cash.

  12. I love the charlotte rubber boots. Can I enter just by commenting here? I am on the only person in the world not on face book! I am sure my kids will have accounts before I do. : )

  13. Hey Shana – I did a little investigating… I ordered through ShopBop and the boots I bought were labeled as “Original Hunter Wellington Rain Boots” but when I checked the measurements against the boots on the Hunter web site they matched those of the Huntress, not the original tall! So glad to have that cleared up – I feel a trip to Nordstrom coming on…
    Thanks again for your help!!

  14. Props for that cartwheel! I don’t know if I can do one but you’ve inspired me to try, even though I feel dizzy just thinking about it. What if I fall and break my neck?! lol Because that is a true possiblity.
    Timely post. I just bought a pair of yellow boots but wasn’t feeling them so I’m exchanging them for some black patent ones. Not sure which brand yet but the Kamik Heidi looks promising. Those are more my style- classic & easy.
    All of your outfits are cute! My favorite is the dress. I would have never thought of that!
    Btw, I also don’t have a FB account. Used to but just got over how much time I wasted on it. Good riddance! Tehe

  15. I think the Charlot Gum rubbers are divine and would love to win a pair to wear with my new red skinnies I plan to wear with everything this spring!

  16. Jenn – My Gap boyfriend jeans are ancient, but they look most like Gap’s sexy boyfriend jean.
    Jaime – That make SO much more sense! You will crack up when you get the real classic talls – your legs would have to be pretty darn skinny to be flopping around in there! πŸ™‚

  17. Such an awesome post, thanks for featuring my boots in the mix!! πŸ™‚
    I love my Loeffler Randall boots, worth every penny. I wear them everyday in the winter here which in Portland = RAIN MUD SOG RAIN. They’re so awesome, don’t look like rainboots and are comfy! Much recommended.

  18. I have been craving a pair of Hunter wellies since I first read this post (a year ago?)…
    FINALLY ordered this morning!
    (Since I didn’t have appropriate boots to wear to Music Train during a Denver spring snow storm πŸ˜‰
    Thank you Shana!

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