Fall Rainy Day Outfit

Happy Monday, friends!!! I hope you had a nice weekend. Ours was busy but fun. Saturday was windy and rainy, and I had plans to meet friends for brunch, so I threw together what turned out to be the perfect fall rainy day outfit. We snapped a few pictures before I walked out the door.

Fashion over 40: This cozy v-neck sweater, distressed jeans, and hunter boots makes the perfect fall rainy day outfit for running around town.

This Gap v-neck sweater is sooooo soft and stretchy and cozy. The drop shoulders and split hem are cute details, and it comes in a ton of colors. I sized down to a small and it’s still quite large, but it’s supposed to be a relaxed fit. It would be more flattering if it fit closer to the body, but I tend to gravitate to more relaxed styles on top especially when wearing legging jeans. This sweater is also just $20 right now! My chunky pointelle sweater is also just $20.

SALE ALERT >> Gap has 40% off the entire store with code ALLIN.

This cozy v-neck sweater, distressed jeans, and hunter boots makes the perfect fall rainy day outfit for running around town.

This teal crossbody bag came in my last Trunk Club, and I was in love the second I pulled it out of the box. It’s such a pretty contrast against the pinks and burgundies I tend to wear a lot, and I also thought it was pretty paired with this orange sweater. I’m enjoying smaller bags these days for a change. It’s just large enough for my wallet and the cosmetic bag I like to carry in my handbag, and the pocket on the back is the perfect size for my large smartphone.

Fall Outfit Inspo: Orange and Teal

My AG Legging Jeans were a recent sale purchase. (They’re back to full price now, but these are similar and come highly recommended.) I seriously can’t stop wearing them. My husband has threatened to hide them if I don’t give them a rest pretty soon. Ha!

This cozy v-neck sweater, distressed jeans, and hunter boots makes the perfect fall rainy day outfit for running around town.

I’m wearing Tall Gloss Hunter boots, but it appears that they grey has been discontinued. The Original Tall style comes in an Ocean color that looks similar. I picked up my boots at a Shopbop sale a few years ago. If you’re in the market for a pair, be on the lookout around holiday time. You can often find them on sale. I am always amazed at how often I wear these and marvel that I lived so long in this area of the country without rain boots. It’s nice to be able to run around in the rain and not deal with cold, soggy feet.

Hunter High Gloss Tall Boots

I wore a short bar necklace to fill in the v-neckline and a longer pendant to add interest to the outfit and draw the eye in and down to waist. I’m also wearing a pair of pearl earrings I recently ordered from Nordstrom.

Fall Fashion: This cozy v-neck sweater, distressed jeans, and hunter boots makes the perfect fall rainy day outfit for running around town.

For years, hoops have been my go-to earring style, and I still love my hoops, but recently I’ve been wanting to add a couple pairs of oversized studs to my accessory wardrobe. I like how they stay out of the way and don’t interfere with scarves or turtlenecks, and they don’t compete with my necklace. I have some oversized faux diamond studs that I’ve been wearing, but I really like these pearls because the bright white color stands out underneath my dark hair.

Gap Cozy V-Neck Sweater in Letterman Orange

There’s certainly nothing original about this outfit, but I love the combination of colors and textures, and I felt cute and comfy running around town on a rainy Saturday. I threw my silver Michael Kors trench over top. I wish I’d taken a picture, but I was running late as it was so we skipped it. My silver color is gone, but it comes in 5 other pretty colors, and I HIGHLY recommend this trench coat. It is very comfortable, and I don’t feel at all fussy wearing it with jeans. It’s also 25% off.

This cozy v-neck sweater, distressed jeans, and hunter boots makes the perfect fall rainy day outfit for running around town.

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Gap Cozy V-Neck Sweater (size down) // AG Raw Hem Legging Ankle Jeans (cheaper option) // Quill Layering Necklace // Engravable Bar Necklace // Faux Pearl Double Stud Earrings // similar Hunter boots // Kate Spade Lavina Crossbody Bag

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19 Responses

  1. I see so little v neck sweaters! Everytime I think, that s a nice sweater it is with a col or round neck. Grrr. Didn t you also own red Hunters!

  2. Funny that you talk about trench coats because that’s my theme for the week on my blog—great minds think alike!! Either that or the weather–ha ha!
    I really like how you layered your necklaces—I think it really adds dimension to the solid colored sweater!
    I don’t even have any rain boots—it really doesn’t rain much here in Denver!!

  3. I sent the mojito recipe to our daughter, as she is the family drink maker! The leaves painted on the glasses make a nice touch! I just love all things fall. Burnt orange & denim is such a great color combination. I just ordered & received a pair of boots the color you are wearing. I had to order the low style, as my calves are too large for the high ones. To me, Mondays are a fresh start, a second chance to get things completed I wasn’t able to finish last week. Can’t wait to see what you’ve got for us for the rest of the week! BTW, You are a really great writer. I so enjoy how you describe things, inject bits of humor into your blog, and keep it real!

  4. You look beautiful, as always.????

    Last year, I was able to get those tall grey gloss Hunter boots for $75 at Costco. They also had other colors. Maybe they will have them this year as well.????

  5. Really cute outfit and I’ve been thinking about purchasing a pair of Hunter boots. Do they run true to size? I’m assuming you wear socks with them and do you like the liners you can purchase separately?

    1. Hunters run a bit large and only come in whole sizes, I believe. I have the size 8. I wear an 8.5 in most boots. I also like to wear my Abeo inserts in them. They actually have a nice arch support built in, but they are still kind of roomy (I assume a 7 would be a bit too short for me) so the inserts take up some room and make them extra comfy to walk in. 🙂 I haven’t bought the separate liners because $$$. I just wear regular boot socks if I want my socks to show, and otherwise I wear regular crew socks.

  6. I bought the Gap pointelle sweater and blue and it’s lovely and feels great on. Doesn’t need a shirt underneath. I may order another one.

  7. I bought the light blue sweater last week waiting for it to come inthe mail, shows an EAT of wednesday, I hope it looks just as good on me as it does you!!! Looks soft!!

  8. Hi Jo-Lynne! I ordered this sweater in the midnight blue color and went back and ordered TWO more!!! I loved it that much! I sized down one size like you did and it’s such a great fit. I wear them out and about and also around the house when I’m cold and want to be cozy. You make the best recommendations!!! Thanks!

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