Building a Timeless Fall Wardrobe

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Fall is such a fun time of the year for clothes.  I think my favorite weather is at the beginning of fall when it’s cool enough to wear a sweater or long sleeves but warm enough to still wear shorts.  I’m living vicariously through all of you since it’s a perpetual 85 degrees here in Hawaii (which I also love, don’t get me wrong!), so I thought it would be fun to share the things that I think make a classic fall wardrobe that will never go out of style.  I own most of these pieces already (old versions mostly) but also included some new finds I’d definitely be wearing if I got to experience fall weather this year.  Happy fall and happy shopping everyone!  

1.  Open-Front Sweater Blazer.  This sweater is great because the blazer cut dresses up any outfit but it’s actually a sweater so you still feel casual.  It works well paired with jeans and leggings and over any sort of simple top.  It’s the layering piece of the season, in my opinion.  I have it in navy but it comes in a multitude of colors.  The camel or gray would be my next choices because they’re so versatile and will never go out of style.  I have the Factory version and I’m obsessed.

2.  Chambray Button-Down Shirt.  Chambray shirts are a year-round essential in my opinion (always go for the lighter option).  They go great with a dark pair of jeans (long live the Canadian tuxedo!), leggings, shorts, a skirt… pretty much everything.  In wear weather I roll my sleeves so that they’re above my elbows, and in cooler weather they look cute under a sweater or puffer vest.  I prefer ones without pocket flaps because those always get messed up in the wash and I hate ironing.  Here and here are two cheaper options.  

3.  Tan Suede Loafers.  I live in loafers in the fall.  They dress up everything you wear and look so cute with skinny jeans.  My tan pair with tassels is 5 years old and they’re still a workhorse in my closet.  This tan pair is a great option if you need a good pair that’ll last you for years.

4.  Large Pearl Studs.  My daily wardrobe almost always consist of a pair of small diamond studs or these large pearls that have really pretty gold detailing.  Julie Vos (a beautiful source for unique jewelry) sent me this pair for a blog post last year and I have continued to wear them all year long.  Pearls are always classic and will never go out of style.  The larger size makes a statement, but this style also comes in a smaller version if that’s more your style. 

5. Align Crops.  These crops are the best because they are great for the gym and running but they also work really well as everyday leggings paired with boots, loafers or mules.  They seriously feel like you’re wearing nothing and the high-rise is super comfortable.  I have them in navy and black but plan on buying this sage color soon.  (My normal lululemon size is a 6 but I size down to a 4 in these.)

6.  Reversible Herringbone Serape.  Oh how I wish I had a use for this in Hawaii, because it is gorgeous and looks so comfy and versatile!  The gray color would go with everything and I love the subtle herringbone pattern.  It’s made by Barbour so the quality has got to be fantastic, yet it’s only $99 (not bad for great outerwear).  By the way, I just had to look it up and a “serape” is a “shawl or blanket worn as a cloak in Latin America.”  Learn something new every day!

7.  Solid Long-Sleeved Shirts.  These are my favorite long-sleeved shirts and I buy a new one every year.  They’re cheap, they fit really well and I love the boatneck neckline.  Mustard is the color of the season but this also comes in a 12 other fun colors. 

8.  Slim Camel Sweater.  J.Crew Factory makes the Teddie Sweater every year and I probably have 10 of them.  They look great with everything!  Most of mine are the older 3/4 sleeve version but this year it looks like they’re all long sleeved.  Camel goes with eeeeeeeverything

9.  Slim Navy Sweater.  This is actually J.Crew’s version of the sweater listed above.  Navy is such a staple in my closet (though this sweater comes in lots of colors).  99% of the time I turn to it rather than black, so a solid navy sweater is an essential in my opinion.

10.  Striped Boatneck Shirt.  This is one of my favorite shirts that I own, and I’ve had it for years!  I always get compliments on it because it’s simple and such a classic.  I wear it with white or blue denim shorts in the summer and with white or blue jeans in cooler weather.  I love pairing it with leopard print loafers.  I’ve also worn it tucked into a pencil skirt!

11.  Tassel Earrings.  These are my go-tos any time I want to wear statement earrings.  They come in a million colors but I think the pearl version is the most versatile.  Lisi Lerch sent me these for a blog post a couple years ago and they’ve been my favorite statement earrings ever since then!  They also now come in a mini version that is slightly smaller and $40 cheaper.  

12.  High-Rise Denim.  You can’t beat high-rise skinny jeans, especially if you’ve had a baby.  We live in Hawaii so I’m not in the market for jeans at the moment but the second we move back to the land of seasons I plan on trying these Madewell jeans I’ve heard so much about.  For another option I always love J.Crew and that is where most of my jeans come from.  Oh and I bought 3 pairs of these Walmart jeans this summer and they are a great super-cheap version 🙂

13.  Cocoon Coat.  I got my version of this coat in 2013 when I lived in DC and I have worn it every fall and winter since then.  It looks good with everything, yet the cut is slightly dressy which ensures you don’t look sloppy when you’re all bundled up.  Comes in lots of colors but I like the traditional tan one.  If you need a good winter coat that will last you years and years I’d highly recommend this one.  Here is J.Crew Factory’s version, which is a bit cheaper though it seems to not get the best reviews.

14.  Ruffle Neck Pullover.  I saw this shirt online and even though I don’t need it right now I ordered it in both colors because I loved it so much.  It’s sweatshirt material but it has subtle ruffles at the neck and wrists which dress it up a bit.  The gray version has chambray ruffles and the navy version has blue and white striped ruffles…both are so cute that I had to get them both!  It’ll be darling (and comfy) with skinny jeans and I know it’ll last for years and years.

15.  Twill Jacket.  These twill jackets are essentially the same every year and they are such a classic.  I’ve had the navy version for about 5 years and it’s a great piece for fall and for spring (this year’s navy version has a hood).  I’d love to add this mossy brown color to my collection but I already have the Old Navy version which is just as cute, though a tad more casual in my opinion.  The quilted version is a great alternative if you want something that will be a bit warmer.  I love layering these with a long sleeved shirt or a slim sweater.

16.  Leopard Print Shoes.  I love leopard print loafers or mules because they seriously go with everything and they’re a great, yet subtle way to embrace such a classic pattern.  I like leopard paired with jeans, stripes, bright colors, brown, black, gray and camel…pretty much everything except navy blue.  My pair of loafers is super old from J.Crew but this mule pair is so nice.  Here is a cheaper loafer version that is just as cute.

17.  Striped Crew-Neck Sweater.  Blue and white stripes is my love language…I cannot get enough.  This one is only $26 and looks like it would be a perfect wardrobe staple.

Oh and if you do decide to order any of these items (or many of the things you happen to discover on my blog) I would appreciate it so much if you did so after clinking one of my links.  I put many hours and lots of work into these round-up posts and will make a tiny commission if you buy anything, but it won’t cost you any extra.  Consider me your personal shopper!  You certainly don’t have to but I would be very grateful.  By doing so it’ll make all the work worthwhile and it’ll allow me to compile this sort of post more often.  I love sharing fashion tips and finds with you but finding all the items and links takes more time than you may think.  Also, I’m on the app which makes shopping my outfits and things I share a breeze.  I’d love for you to follow me there (same username as my instagram handle: lifewithadashofwhimsy)!  Thank you for your support and for following along on all platforms.

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Katie Vail
Katie Vail

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Leave a comment

  1. October 3, 2018 / 10:56 pm

    How are you in my head? This is pretty much EXACTLY my fall wardrobe/the holes I'm trying to fill in my closet! Thanks for some new ideas for those holes 🙂

    PS: Next year, for my 30th, I am planning a trip to Hawaii – can I reach out to you sometime for some ideas/tips? 🙂

  2. October 5, 2018 / 5:06 pm

    I appreciate this post, I love trying to have timeless pieces in my wardrobe. Bought the sweatshirt in navy and I made sure I went through your link! Thanks for this post!

  3. October 5, 2018 / 8:09 pm

    Thank you so much! I really appreciate that and hope you love the sweatshirt as much as I do!

  4. October 5, 2018 / 8:11 pm

    aww that makes me so happy to hear! Hope you're able to fill those holes with some timeless classics 🙂 and yes, absolutely! Feel free to reach out at any time. Also, check out my friend Kait's blog, she has lived in Hawaii for about 7 years and does the best Hawaii blog posts. Our styles are similar and she won't steer you wrong!

  5. Brianna Hughes
    October 7, 2018 / 3:40 pm

    Omg that cacoon coat is so beautiful!!! 😍

  6. October 7, 2018 / 10:45 pm

    Isn't it so pretty? I've owned mine for half a decade and I know it'll last at least 15 more years, it's such a staple!

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