Fall is FOR SURE the time of year when I spend the most money. It is also the time I wear the most money. Literally, almost every day during fall, my outfits cost more than the amount of money I have in my bank account. It’s not okay. But fashion wins.

During fall, I always feel like I’m starting over. It started in elementary school when I would buy my new wardrobe for the year in fall – and it continued through high school and college. Now, I’m not in school anymore, and my life is a constant cycle of same shit, different day, but I can switch it up and make things new again by revamping my closet. Even if I already owned the items, I haven’t seen or worn them in months – so fall clothes literally always seem new, no matter what.

Over the years (and in the past month) I’ve made some big investments in my wardrobe during fall. Boots, new workout clothes, jeans, long sleeve dresses, jackets, etc. Here are the  best investments I’ve made for fall fashion in the past couple years:



Black Booties.

Last weekend, I strolled into Nordstrom with a $32 note and a fierce determination to find myself a casual pair of black booties I could wear to work without looking too dressed up, but also still fashionable. After trying on five different pairs of shoes three times each, I decided on these unique Jack Rogers black booties. I had never tried on a pair like them – and since buying them, they’ve gotten compliments galore.


If you’re wondering, the dress is also a new purchase from Madewell, which you can get at Nordstrom. And the leather jacket is from somewhere in Italy. It was a gift.


Cognac Booties.

I got these cognac-colored BP booties a year ago this month, and I am still excited about wearing them. Whenever I put them on, I automatically feel fancy, fashionable, put together, and ADULT.


The dress is from Nordstrom Rack and the denim jacket is from J. Crew Factory. I should note – everything at J. Crew Factory is 50% off right now (whaaaaaat)… and they’re selling the jacket I got at Real J. Crew last year now – and it’s 50% off the factory price, so GET TO IT.


Peep-toe Booties.

As we all know, fall is the BEST time for peep-toe booties. But you never want to buy them, because you only have a month to wear them. Well, this past June, I bought myself this pair of Vince Camuto peep-toe booties ($129.95). They aren’t really booties, actually, but they also aren’t sandals. I wore them occasionally during summer, but now is really their time to *shine* because with jeans, a top, and a blazer, these shoes are [fire emoji here].


This picture is NOT from fall, duh, but the jumpsuit is Topshop if you’re wondering. It’s not for sale anymore, but they do have lots of fabulous other jumpsuits that I can’t afford.


Tall Frye boots.

I bought these in the fall of 2011, and they are still by far my favorite and most comfortable pair of shoes. Also – THEY ARE ON SALE RIGHT NOW for only $299, which is an insane price for such a fantastic investment. I got mine for around $450 – and while the price has gone down, going all the way down to $299 is key. The fact they have lasted five years so far, and have many more years left, says enough.


Now, let’s dive into jeans.



I hate pants. I actually absolutely EFFING HATE PANTS. I mean, I like yoga pants I guess. But the idea of strapping myself into a pair of jeans is just not something I enjoy doing. SO THANK G I FINALLY TRIED ON MADEWELL JEANS, because they changed everything. Madewell jeans are high rise and comfy and HIGH RISE and I love them.

The best part (for you – not me) is that the jeans I just bought like two weeks ago are now on sale (fuck me, right?). You can get them for $76.80, when I bought them for $128. I’m pissed, yes, but I might buy another pair – you win some, you lose them. You’re welcome in advance for changing your life. There’s a reason celebs wear these.

The other stuff in the pic —


Light wash ripped jeans.

To break away from all of my dark skinnies, I got a pair of Treasure&Bond ripped jeans and fell in looove. They’re so cool and casual. Not on the same comfort, high rise level as Madewell jeans, but close. Also, giraffe shirt = goals, I know.



And some *important* additions to my closet – dresses and shirts.

This plaid shirtdress from Madewell.


Obviously I have an addiction – and it’s bad, but whatever. I bought this a couple weeks ago and I am obsessed. Every time I wear it, I feel like I should be going apple picking. Too bad I hate apple picking. Also, I just learned how to do a top knot.


Anything cupcakes and cashmere.

Emily Schuman (founder of the blog and home/clothing line, cupcakes and cashmere) is a boss and I want to own all the things she makes. I snagged this dress at the Nordstrom anniv sale in July and have worn it multiple times since. Side note: It is only $68.98 right now – and when I got it, it was $115! 


Shoes: Sam Edelman – these flats are so comfortable, and I found this pair at Nordstrom Rack, which was great because they sell this pair at full price still in diff colors. I FOUND A STEAL, YA’LL. Necklace: Madewell, where I get all of my necklaces from. Secret (?) is out.


A crushed velvet tank.


I got this at a boutique in NY, so I’d look around.


And finally, a FALL NECESSITY – Rain boots!

My short, black Hunter boots were a hard investment for me – I don’t like buying things that everyone else already owns, and rain boots are rain boots – I’d prefer to spend my money on more fashionable boots. But this purchase was a fab choice. I’ve owned these for about three years, and they’re still doing great. I recommend, even if they are the most basic rain boot ever. There’s a reason everyone has them!


Hi I’m Sam. I made this website in 2011 and it’s still here! I'm the author of the humorous self-help book AVERAGE IS THE NEW AWESOME. I like pizza, French fries, barre, spin, more pizza, more French fries, and buying clothes. Follow me on twitter & Instagram at @samanthamatt1... and on this site's meme account on IG at @averagepeopleproblems. OKAY GREAT THANKS BYE.

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