What Do I Wear There? Fall Weather Fun

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Fall weather fun

Last week, reader Jenny wrote in with this question:

“There is a theme park near where I live, and I go there a lot with my friends. I was wondering if you had any ideas of what to wear for a day out at a theme park or carnival- it’s difficult to know because I’m running round all day and any jewelry I wear is very irritating because I have to keep taking it off on a roller coaster.”

This got me thinking about other fun fall activities that we all may be running out to enjoy before winter sets in. Besides Jenny’s idea of going to a theme park or carnival with friends for a day, I also thought of going pumpkin or apple picking (yum!) and going on a road trip during one of November’s long weekends (which is absolutely the most fun in the fall with all of the leaves turning gorgeous colors).

So instead of only answering Jenny’s question, I figured I would come up with looks that would work for each of these events to ensure you have the best end-of-fall ever!

Look One: Carnival Clothes

What to wear to a fall carnival

Product Information: Plaid Flannel Tunic: Old Navy, Vintage Wash Jeans: TopShop, Bow Earrings: American Eagle, Studded Converse: Singer 22, Tinted SPF Moisturizer: YesStyle, Nail Polish: Forever 21

Comfort is key to having a fun day at a carnival or amusement park. You want your focus to be on having the loudest scream or keeping your arms up the longest on the roller coaster, not on whether your shoes or jewelry are going to fly off!

Therefore, I suggest going for a trendy but cozy flannel like the one above. You’ll be comfortable but still stylish. The flannel I chose is especially great for the amusement park since it has a tie around the waist. That way, you won’t have to worry about your top moving if you are on rides that turn you up, down, and all around!

Pair this top with your favorite pair of worn-in jeans that are comfortable whether you’re walking around or sitting down (since you will often be sitting for rides). Throw on a cute pair of sneakers to complete your comfy-cool look–Converse are always a great choice and the stud detail on these makes them totally stylish for this season. You could probably even DIY them yourself with an old pair of Converse – be creative!

As Jenny mentioned, jewelry is tricky when dressing to go to a carnival. You do not want to wear pieces that could dangle or get caught, and you definitely don’t want to wear anything you would be super upset to lose. (It happens!) Therefore, I suggest going for a cute pair of studs–definitely not dangling earrings–to add a little extra sparkle to your look. These bow studs add an unexpected girly element to an otherwise tougher look.

For your hair and makeup, keep it simple but be smart. And by smart I mean wear sunscreen! You’re going to be out in the sun all day and even though the strong heat of summer is gone, you are still susceptible to those harmful rays. I personally love tinted moisturizers with sunscreen, as they give you good color as well as SPF protection. Since this outfit includes earrings, pull your hair back to make sure it does not get caught on them when you’re on rides. And finally, indulge your inner carnival-loving child with some funky bright red nail polish (this color will work with almost any of the outfits in this post)! Red is a classic shade that’s perfect for fall.

Look Two: Apple/Pumpkin Picking Attire

What to wear apple picking

Product Information: Knitted Sweater, Shaggy Scarf: TopShop, Jeans: Piperlime, Leather Gloves: JohnLewis.com, Black Boots: Piperlime, Pearl Bobby Pins: Monsoon.co.uk

Some of my favorite memories of fall are all the times I went out pumpkin picking when I was little. From the hay rides to the delicious fresh food and the actual pumpkin picking itself, there’s nothing more indicative of the fall season to an East Coast-er like me than trekking out into those fields. And luckily, this is one of those activities that only gets more fun as you get older! This is another situation in which you want to make sure you stay comfortable since you’re going to be moving around so much.

A great fall style that is perfect for this activity is the “boyfriend” look. An oversized, boyish sweater will definitely keep you warm and cozy, while a pair of skinny-fitting jeans will keep the look from being sloppy. Put on some durable black boots (I love the zipper detail on these ones) in case you have to stomp through some mud to get the best pick, as well as gloves so that you don’t have to get your hands too dirty (and because sometimes the trees/stems of these fruits can scratch you).

To add some extra warmth (in my experience, pumpkin patches are often windy!), add on a textured scarf in a dark color that will not compete with the pattern of the sweater. For your hair, I think a side braid or chignon would be a perfect way to tie the whole look together, especially if you hold it up with these adorable pearl hairpins.

Look Three: The Perfect Road Trip Outfit

What to wear on a fall road trip

Product Information: Tunic: Monsoon.co.uk, Dark Wash Jeans: TopShop, Sunglasses: ModCloth, Rust Shoulder Bag: Piperlime, Necklace: Missselfridge.com, Boots: Nyciwear.com

While road tripping with your friends is going to be fun all year round, taking one in the fall has the aforementioned advantage of having the best roadside scenery. Plus, what better way to blow off post-midterms steam than belting songs out the window with your best friends?

The only potential downside to a road trip is the amount of time you may be stuck sitting in the car. That’s why you’ll definitely want to pick out the most comfortable bottoms you have–my favorites are stretchy, skinnier jeans, but if you prefer a different style or even leggings, go for that! Put on a loose, airy tunic for a cool 70’s vibe on top, highlighted with a funky, multi-strand necklace.

I used those gorgeous fall leaves as inspiration for choosing the accessories, picking rich, chocolate brown boots and a deep, rust orange tote. And, of course, no road trip–or as far as I’m concerned, trip anywhere–is complete without the perfect pair of sunglasses. The geometric shape of these adds a modern aspect to the otherwise more boho look, and the shades should be dark enough to allow you to drive facing even the brightest sun!

What Do You Think?

Do you typically partake in these fall weather activities? What outfits have you worn for them? Did I miss any activities, clothing items, or accessories that are great for fall? What are your favorite pieces to wear in this fall weather? Share below!

And as always, if you have a “What Do I Wear There” question, leave it in the comments! You may be featured in next week’s article.

36 thoughts on “What Do I Wear There? Fall Weather Fun”

  1. im going to the dave matthews band concert this novermber (2010) its about two weeks away right now and i would like some ideas as to what to wear. i want to look really cute and get some guys but i dont want to be freezing since ill be tailgating

  2. I actually love these outfits. My only concern is the sleeve length on looks 1 & 3. Do you have anything a little warmer, for us East coasters? I lack in the fashion area, so would you just put like a heavy coat over these shorter sleeved shirts?

  3. I would also like to know the answer to Kate’s question. I am going to Spain next month, and I have no idea how I am going to pack 2 weeks worth of clothes in 2 suitcases.

  4. I’m currently living in Melbourne, Australia where the temperature is 90 degrees on a regular basis. I’m going back to my home town Anchorage, Alaska for December to spend Christmas with my family. How do I take my summer wardrobe and make it into a winter one?


  5. I really love the road trip outfit! The fall colors are adorable. The others are cute too… they could use a little more more color maybe, but they look really comfortable.

  6. As always, I love your post! I adore all the outfits, they’re actually comfy and warm looking and still fashionable, exactly what I like. I love how you’re able to add these little details to make it all ‘click’ and have me immediately form a whole picture/idea in my head, example here being the side braid/chignon with outfit 2. I already liked it, but that little tip made everything just fall into place! That’s a great talent!

  7. great post!
    i have a question as well!
    I want to start wearing heels but so far I wear only converse and flat boots…therefore I need to start easily!any ideas?

  8. Yay I am so excited that you are going to write a study abroad post! I think it will help a lot of people (I always tell my friends to read cf and a lot of them are going abroad too).

    London will be so exciting! I am going to rome, italy! and most of my friends are going to barcelona or seville.

  9. Hey for the what do I wear there can someone do an article on what to wear to a semi-formal dance?
    My sororities semi-formal is coming up and I don’t know what to wear

  10. Hey guys! I’m glad you seem to like the outfits this week!

    Romney: For colder weather, I have a couple of suggestions. Both outfits could look cute with chunkier knit sweater/cardigan on top if it isn’t too cold out. If you are still cold with that on, I would put your heavier coat on as well.

    Kristina: I totally know what you mean–the last time I went to a fashion show I was so freaked about what to wear! I’ll definitely try to answer this question ASAP. As for the breast cancer/pink thing, I think that you do not have to wear head-to-toe pink. However, I would then wear a neutral color (black, white, grey, beige, etc) with pink accents, like a pink cardigan on top, pink nails, pink jewelry/headband, or even a super bright pink lipstick. Hope this helps!

    To address the rest of your questions:

    Study Abroad: I am actually thinking of doing a sort of study abroad series about essentials to bring with you and tips from friends of mine who have gone. I am actually going abroad next semester as well (yay London!), so I am really excited for this! Let me know if you would be interested, as well as where you’re going so I can feature some of the popular destinations.

    Colder Weather: I have touched upon some good ideas for colder weather that would help those of you moving into winter weather. Other CF writers have written awesome articles as well on this topic! I suggest searching “winter” or “cold” in the search bar on this site to look at the articles already up. If you still have questions, let me know!

  11. I love you blog! I am definately a regular reader!

    Q: I live in Norway and it has already starter snowing and it’s around -5 degrees celsius here every day. I was just wondering if you had a good outfit with som warm shoes/boots and a warm coat + accesories like a hat, gloves, scarves. Because I have to walk about 3-4 km to school every day, and it get freezing cold.


  12. I really love the outfits for winter! They look so snug and cute at the same time 😀

    I third (or fourth?) Kate’s request – my class is going to Sofia, Bulgaria in a month or so and I’d love to know what to bring. I don’t want to bring too much since we’re going to be walking everywhere and staying in a small hotel… but I don’t want to be wearing the same 3 outfits for the whole time. I’m not sure what the weather will be like, but I’m expecting it to be quite cold and snowy.

    Also, I have another request: I have to walk to college every day and it’s quite a hike (40 mins up a huge hill) so by the time I arrive I’m usually quite sticky and my hairstyle’s completely ruined, but throughout the day I’ll get really cold. What can I wear that’ll keep me cool when I walk to college, but warm throughout the day? And how can I prevent my hair from being a complete mess by the time I arrive?

  13. Wow I love all the outfits your put together! I especially love the second one; it’s so me! Especially since I’ve been coveting that sweater ever since I saw it on the website. Great post!

  14. I love all of these outfits! I’m a bit sad that they don’t seem to be selling the plaid tunic from old navy online anymore though. 🙁

    I second (third?) the requests for packing to studying abroad – I studied abroad last year, and I had the HARDEST time packing (both going to there and coming back – with all the extra stuff that I bought).

  15. I love the pumpkin/apple picking outfit!

    I have a question…what do I wear to fashion shows? Especially ones that are more local with random labels that I might not own any of or fashion shows that feature an assortment of local boutiques. I also have tickets to a fashion show thats a benefit for breast cancer and the theme of the show is pink (obviously) but i do not look good in pink. Is it rude if I don’t wear pink?

  16. Love all these outfits! It may just be me, though, but I don’t actually find jeans very comfortable. Low rise ones are the worst – although they can look nice, I have to keep pulling them up (even belts don’t help!) And they seem to dig in at the wrong places when I’m seated (but that’s probably because I sit in funny cat-like positions!) So, for me, I wear jeans when I know I *don’t* have to be comfortable. For comfort, I always pick leggings or tights! 🙂

  17. Thanks so much for answering my question- I love all those outfits! Great job 🙂
    I agree with everyone who was asking about outfits for study/trips abroad- that would be really helpul! I love that you feature Topshop/Monsoon/Miss Selfridge by the way- it’s really useful for us UK readers 🙂

  18. i love all of these outfits! Great job.

    So, i’ve got a question. i’m going to new york in late december and i have never been that far north and i have no idea what to bring with me or what i should make an essential. what would you reccommend? Thanks.

  19. I have a question too, what would you pair with black pumps so that the outfit doesn’t look so formal or nightclubby?

  20. Must be nice not going to school in the Great White North :3

    Giselle, where at in NC? It’s got some pretty varied climate (I grew up there). If you’re going into the mountains, I recommend cute scarves and hats, because the wind can get pretty stout.

  21. I have a What Do I Wear There question! I’m from Miami, but I’m going on a trip to North Carolina soon. The last time I was in cold weather was years ago! My style has definitely improved since then, but I’m completely clueless about fall/winter weather. What are some stylish and basic items I should have?

  22. All outfits are cute! I have a request. What to wear to a concert (rock/rap). I want to be cute AND comfortable lol.

  23. I second Kate’s request! I’m also going abroad (okay, next fall, but I don’t mind planning ahead!) and I’ve been wondering how I’d fit everything into two suitcases. I’m a little nervous about standing out as an American too, since I feel like Italians are a million times more fashionable than I am.

    I love the first outfit! Totally perfect for early fall before it gets too cold. I really like the second one too, but I’d probably add in some extra color if I were wearing it myself.

  24. Great post! It’s allllmost cold enough for me to start wearing more fall-like clothing. (I live in California.) If anyone is looking for cute plaid flannel shirts, try Target! I just got a blue one, and they have a lot of other colors. They’re fitted and have snaps or buttons. I’m wearing it today, but I’m already thinking about how I can layer up in the coming months.

  25. I love these looks! I especially like the second look because its warm and cozy yet still put together.

    I have a request for a new post: I’m going abroad to Italy next semester and I really need help! How do you pack everything you need in 2 suitcases? What types of outfits can you bring that can be reinvented in multiple different ways? What kinds of outfits should I bring that would work for going on trips to museums and walking through ancient ruins that are stylish and but still comfortable?


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