How to Style Rain Boots for Fall

Happy Monday! We had a discussion a while back on my Facebook Page about Mondays. Despite their less than stellar reputation, I actually love Mondays. I love the feeling of a fresh start and a blank slate. Today is even better because there’s no school for the kids, thank you, Mr. Columbus, so I don’t have to cajole anyone awake or shove them out the door at any specific time. I’m sure I’ll be ready to shove them out the door at some point in the day, but for now, I’m enjoying the stress-free morning!

I often think of spring as the rainy season, but here in Pennsylvania, we get plenty of rainy days in the fall too. Last week we were feeling the effects of Hurricane Joaquin, and I spent several days my rain boots. I wore this is the outfit one day to run errands, eat lunch out with my hubby, and then to my daughter’s birthday party that night.

Fashion Over 40: Styling Hunter Rain Boots for Fall

I love my Hunter rainboots. I picked them up on a 40% off sale at ShopBop a few years ago. I’d been wanting rain boots for years when I bought these. I ordered a few different brands so I could review them in a blog post, and I decided that Hunters are classics for a reason. These boots are incredibly comfortable. The footbed has a lot of support. In fact, when my foot pain was at its worst, I would wear these all day long. I like them best with my Abeo orthotics, but even without, they have great support. Plus, they’re just gorgeous. The others went back, and needless to say, these were the keepers. 

Fashion Over 40: Styling Hunter Rain Boots for Fall

You can find these Hunter Original Tall Gloss Boots at ShopBop, Nordstrom, and many other retailers. Mine are Graphite.  I chose the color for their versatility, and I don’t regret it, but if I lived in a wetter climate and could justify two pairs, I’d definitely get a 2nd pair in Military Red. I love that color. SO fun.

That said, if you are going to have one pair of rain boots in your closet, I recommend a neutral because it’s so versatile.

You can pair rain boots with a skirt or dress, but I usually wear them with pants. Choose pants that will easily tuck in to your rain boots. Skinny jeans or leggings are perfect. Because it was so chilly, and also to add interest to the outfit, I wore my cream-colored boot socks. I don’t have the Hunter Wellie Socks because $$$$. I just have regular old boot socks. These are similar.

Fashion Over 40: Styling Hunter Rain Boots for Fall
On top, wore this Harvest Morning Pullover from Glamour Farms. I’ve worn this pullover at least once a week this fall. It’s so easy to wear, and the color is perfect for this time of year. The cropped skinny jeans (similar) fit easily into the boots and help offset the relaxed styling inthe top.

Fashion Over 40: Styling Hunter Rain Boots for Fall

For accessories, I wore gold teardrop earrings, and I carried my snakeskin satchel. I like how it combines the grey from the boots and the oatmeal color from the socks.

The sage green raincoat (shown above) is as old as the hills, but it still comes in handy from time to time. Sage and pumpkin are a great fall color combo, dontchathink? Speaking of which, I wore this Harvest Morning Pullover with my olive green utility jacket when I was in the Poconos a few weeks ago. That was cute too!

Fashion Over 40: Styling Hunter Rain Boots for Fall

Outfit Details: Harvest Morning Pullover | Hudson ‘Krista’ Super Skinny Cropped Jeans (similar) | Hunter Original Tall Gloss Rain Boots | boot socks (similar) | Goddess Teardrop Earrings | snakeskin satchel (similar

Enjoy your Monday!

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27 Responses

  1. I certainly got my money’s worth out of my Hunter boots over the last week with all of the rain here in Columbia. That pullover is great. Thanks for the link!

      1. Thank you, Ginger. It’s going to be a long road, but our friends, family and neighbors are coming together to get the job done as best we can.

  2. CUTE! I rarely wear mine and they fun (black and white plaid). We usually don’t get much rain in the fall. Spring it’s a mess. I should wear them then.

  3. Hi, I would like to order the Hunter boots but sure on sizing. Do they run big/ small, do order my normal size?
    Thank you! Liza

  4. I really like the outfit Jo-Lynne, especially your rain boots. When I buy a pair of boot socks, wouldn’t it be better to buy a neutral color that will go with more things? I have a pair of rain boots that are styled like pointed toe cowgirl boots and are multi-colored paisley print. I will definitely have to be cautious with what I pair them with. The brand is Ride Tecs and they too have good support. Have a great day!

  5. I love that Harvest Morning Pullover- such a great fall color. I gave away my rain boots to someone who would use them more than me. For now, when it’s raining, I wear my hiking boots. If I decide to get another pair, I would consider investing in those. 🙂

  6. Guess I should go to Pennsylvania if I want some fall weather. Our high was 91 in East Texas today! All my cute fall clothes are just sitting in my closet and my son has outgrown most of his summer shorts and tees, but it’s still hot!

  7. Hi Jo-Lynne,

    You have a pair of cute olive green rainboots on in your inset pic at the top of your blog. Can you tell me about those? Fortunately for me, we get our fair share of rain here on the Oregon coast so I wear boots a lot!!

  8. Just discovered your blog and am really enjoying it! I’m not quite 40, but am loving your fashion as I cannot and do not want to wear the style found on the majority of 20-somethings blogs. Anyhow, just wanted to weigh in on the Hunter boots. I recently purchased a pair for my trip to Ireland and love them. I wore them all day walking around and they were totally comfortable. I did get a little warm in them, but it also may have been the socks I was wearing. I love the gray color you have and was leaning towards those, but they didn’t have the “travel” ones in gray, so I went with navy to match my raincoat. I normally wear a size 8 or 8.5 and my Hunter boots are an 8. I’m really having trouble finding boot socks, so if any you lovely ladies have recommendations, I’d love to hear them. Thanks!

    1. Hey Veronica. I’m so glad the Hunters were comfy on your trip! That’s good to know. I had a hard time finding cute boot socks to link to for this post. The ones I have are long gone. I will keep an eye out! The Hunter brand ones are incredibly $$$$$.

  9. Do your Hunters powder on the outside? I can’t get rid of it 🙁 I actually am thinking of getting a pair of matte ones because of it. Emily has matte and they don’t powder.

      1. Apparently it’s normal and you are supposed to wipe them down but as soon as they dry, it’s back. It’s so sad…mine are purple so it’s super noticeable 🙁

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