Investment-Worthy Fall Wardrobe Staples

fall wardrobe staple investment pieces classic fall style

outfit details:

camel vello fleece park slope turtleneck | curvy toothpick jeans | leopard loafers (old, current options here and here) | pearl and diamond studs | sunglasses c/o Mohala Eyewear (now available at Nordstrom too!)

My wardrobe tends to contain a mix of highs and lows, and my house is the exact same way.  I love a good deal and am no stranger to Walmart and Amazon, but there are certain core pieces that I have found that are worth spending a little more on.  Timeless and well-fitting pieces are really important to me, so for things that I splurge on (and by splurge, the most expensive thing here is $390 but the average price is probably ~$150), I want them to have longevity.  Here are the fall pieces I’ve found that are absolutely worth the money that last me year after year.

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fall wardrobe staples - bean boots - leather boots - longchamp le pliage tote - birdies loafers - barbour coat - dudley stephens fleece - classic style - grandmillennial style

1.  Dudley Stephens Fleece Turtlenecks– Never would have thought that a fleece would be on my must-have splurge list, but then Dudley Stephens came along and now I live in chic turtlenecks that happen to be fleece.  See my DS size and style guide herePark Slope is my favorite style.

2.  J.Crew JeansThe Curvy Toothpick has been a longtime favorite, but lately I’m really into their demi-boot cut jeans.  These jeans cost more than some other places like Target or Old Navy but the quality is far superior and if you get a well-fitting pair they’ll last you for years.

3.  Sunglasses– I’ve been working with Mohala Eyewear since early 2020 and they’re the only sunglasses I ever wear anymore.  They’re beautiful, well made, and every pair sold sends a girl to school through the non-profit Room to Read.  Pikake and Lana are my favorite styles and code katiev saves you 10% on your first purchase.  I’m wearing Lana in Black Lava in the photos in this post.  The style in the collage is Pikake in Amber Tortoise.

4.  Longchamp Le Pliage Tote– A Longchamp Le Pliage tote is one of the most timeless things you can own.  And since the body of the bag is nylon they are also very easy to keep clean.  I’ve owned mine for over 10 years!  The large size tends to be my most used these days, since I carry so much stuff for the kids.  I used to prefer the small size though.  I love the version with the black base and brown handles  because it allows you to wear it with so many things, though a large navy and brown one is probably next on my list (I already own the small version).

5.  Statement DressesMadison-Mathews dresses make me so happy.  They remind me of Charleston (where the shop is located) and the block prints are so much fun.  The cotton is comfortable even on a hot summer day, and you can easily dress them up with heels or down with sneakers or sandals.  They’re a bit of a splurge but they quickly become a happy dose of sunshine in your closet.  Juliette and Folly are my favorite styles, and the Folly Midi with long sleeves is particularly great in cooler months because it looks great with boots.  My blog post all about the different styles I’ve tried as well as sizing info, can be found here.  Code KATIE saves you 10%!

6.  Loafers– I’ve loved wearing loafers for close to a decade but my life changed last year when I bought a pair of Birdies.  No joke, they feel like clouds.  I have the taupe leather version and I’m hoping they bring back the leather versions this fall so I can buy the cognac color (the current suede version would get you a similar look though).  They run tts and if you get them they’re sure to become your most worn pair of shoes.  J.Crew Factory has some similar-looking options at a more affordable price.  Leopard is always a great basic to have, too!  I’ve had my leopard loafers for close to 10 years and I’m always excited to break them out every fall.

7.  Feminine Flats– I always love to have a pair of dainty flats with a small bow, either ballet or point, in regular rotation.  Margaux makes beautiful ones (I love my Pointes in Rose Napa), as does J.Crew.  This season I really love the look of ballet mules (Margaux’s version here)!

8.  Bean Boots–  Tom’s dad was a game warden in Northern Maine and they used to be issued bean boots as part of their winter uniform…so he doesn’t quite understand why all of us millennial women are wearing bean boots for fashion (lol).  These are definitely my go-to when it’s mucky or freezing though.  I have the unlined pair which I prefer for fall or if it’s mucky or raining, and then I break out my shearling lined pair of Bean Boots when it’s snowy and freezing outside.  They keep your feet toasty and dry, even on the coldest of days.

9.  Coats– J.Crew has been a favorite for warm, classic, coats for years and years.  This season I really love the look of the Daphne top coat and the Blazer-Jacket (very chic with the tie waist- I’d get it in Soft Brown).  I’ve noticed that J.Crew Factory tends to offer similar coats, but the quality is nowhere near J.Crew’s coats.  Just an FYI!  Barbour is a new favorite though and it’s rugged and durable yet looks stylish too (more sizes available here– I am a true size 4 but sized up to a 6 in my Barbour coat so that I can layer underneath).  If you don’t want to splurge on a Barbour coat, this J.Crew field jacket looks very similar.

10.  Sweater Blazer–  If I want a cozy layer and it’s not quite coat weather yet, chances are I’m wearing a J.Crew sweater blazer.  Mine area few years old and I still love them so much, and the current version looks virtually the same.  I own them in navy, camel, blush, and leopard and they’re the best layering piece ever.  Plus they have pockets!

11.  Tory Burch Cardigan–  I very rarely wear anything with a logo, but I love the Tory Burch Simone Cardigan.  I own it in navy and it’s great for throwing over a tank top on a summer night.  I bought mine in 2011 and it’s been a staple in my wardrobe ever since.  It runs true to size.

12.  Burberry Scarf–  I love the gauzy Burberry scarves because you’re able to wear them all throughout the year.  The heritage stone color look great with camel, black, cream, gray and can work with red or blush too, and mine has been a staple in my wardrobe for the past 10 years.  Definitely my most worn scarf I’ve ever owned.

13.  Stacked-Heel Ankle Boots–  A good heeled boot will last you years and years, and J.Crew always has the best ones.  I still wear mine that I bought in 2013!  I love the look and feel of suede boots but you can’t go wrong with leather either.  I like ankle height because they’re great with demi-boot crops, straight leg, and skinny jeans.  You can also wear them with tights and a skirt or dress.

14.  Stacked-Heel Knee-High Boots–  With dresses I love the look of a leather knee-high boot, and I have last year’s version of this pair.  They’re very comfortable and easy to walk it (don’t be intimidated by the heel!) and they look so chic.  I tend to wear brown more often than black, but the black pair is beautiful too.

15.  Puffer Coat–  On frigid days I always default to a long puffer coat.  They keep you so warm and even though they’re quite casual they are definitely worth the investment.  I bought my long black one back in 2013 and still grab it frequently during the cold fall and winter months.  Last year I got this navy puffer coat from Joules (c/o) and it became a quick favorite.  The faux fur collar and the hood are both detachable, so you can change up the look of the coat quickly!  Another option would be this Quilted Cocoon Puffer from J.Crew.

fall wardrobe staple investment pieces classic fall style

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Katie Vail
Katie Vail

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