Getting ready to switch your closet over and feel like if you’re missing some fall wardrobe essentials? May this list be your guide!

Autumn is by far my favorite season. Spring is a close second, but autumn definitely wins out. The way the world just bursts into color breathes as much life into me as seeing the delicate pink blooms of cherry blossoms in the late March. I get a specific kind of giddy when I find myself walking along a street, breathing in crisp air, and hearing the crunch of leaves beneath my feet.

I will say the thing I struggled with has always been fall fashion. The problem is that there’s just so much opportunity! You can be as casual as a sports fan and as dressed up as Anna Wintour during Fashion Week. When I was younger, I had no money to buy the kind of outfits I wanted, and as I’ve gotten older, I don’t fit into most of the brands I could spend money at if I wanted to. Plus teaching elementary school kids in the countryside for my early twenties meant I was often in comfy clothes more than anything else.

Last year was the first time when I really felt like I had a full range of fall wardrobe essentials that fit me perfectly. From hats to shoes, I’ve made a list of what I think really helped me narrow in on feeling both stylish and comfortable. Hopefully it helps you too!

IMPORTANT NOTE: As always, I encourage conscious consumption and these aren’t just “products you must have.” Rather, I made each point more general so you can fill in the blanks with your own personal style. Don’t take this list as an absolute MUST-buy and always shop your closet first. I bet you probably have most of these fall wardrobe essentials already!

11 Fall Wardrobe Essentials from Top to Bottom

hand me down hat - fall wardrobe essentials

1. A hat you’ll actually wear

Here’s the deal – almost every fall wardrobe essentials list written by a millennial features that classic wool, western-style hat. You know what I’m talking about. I love those hats! However, they aren’t suited to everyone, and there’s no point in buying them and letting them take up closet space if you don’t actually like them.

If you do want to wear hats in the fall, look for styles that suit you. Like trendier styles? Why not a warmer-style bucket hat? Newsboy hats can look so cute with a girlier outfit and are less space commitment. Berets are always quite classic even if they’re total tourist cliches in Paris. And, of course, for more casual looks, you can never go wrong with a baseball cap.

If I wear a hat at all, I’ve been loving this newsboy hat pictured above. I actually got it from my friend because for some ridiculous reason she had two, but it’s been great for those traveling days where I don’t want to wash my hair!

SHOP BELOW

red lipstick - fall wardrobe essentials
Example of Lisa Eldridge’s Velvet Dragon

2. A cooler weather lipstick

I’m a big fan of lipstick and have enough that I’ve put a ban on myself from buying anymore for now. They just easily liven up any outfit, and can take a plain look to something a little more special. Trust me, if you’re feeling blah about how you look, just swipe some lipstick on and see it work wonders.

One of the fun things about fall is switching up the shades you wear!

Here are some of my favorite brands:

  • Lisa Eldridge – I am obsessed with LE’s make-up but especially her velvet and luxuriously lucent lipsticks. They have nice staying power but will come off easily if you’re eating and don’t want blotchy lip color. For fall, I love switching to Velvet Cinnabar (a warmer, browner red) and Painterly (more neutral and mauvey)
  • Maybelline SuperStay Matte Ink – This is a liquid lip and it truly does stay put. My only issue with it is that if my lips are even a little dry, it can feel flaky. Also, it will start coming off patchily if you eat something oily.
  • Chanel Le Rouge Duo Ultra – I really like this liquid lip duo from Chanel. Obviously it’s 4x the price of the Maybelline, so it’s very much a luxury product. But I love how it feels on my lips, and I’m an even bigger fan of the clear lip gloss to help things say moisturized. I have Daring Red and Passionate Red.

Another fave was Etude House’s Lip Mousse but they don’t make it anymore *sobs*.

everlane wool turtleneck - fall wardrobe essentials

3. Classic, fitted tops

Ok, so I feel like most people will tell you a crisp, white button-down shirt is a fall essential. However, I disagree. If you have anything over a B-cup, you know it’s a struggle. Most times you’re either choosing between it gaping at your chest or being a touch oversized. Which can be a cute look, but not necessarily an essential in my book.

Instead, I would recommend looking into nice, fitted tops with a little stretch. Nothing super tight, but just something that skims over your body to show off your silhouette. Think Shiv’s looks in “Succession.”

The key is finding the necklines that look best on you and to wear a good bra underneath (Wacoal T-Shirt Bras are my go-to). Think V, round, boat, etc and then finding them in the fabric you like best. I’m partial to a turtleneck or mock neck in fall and look for them in knitted styles. Depending on your fall weather, you can even do shorter sleeves which always look stylish with trousers.

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4. transitional sweaters

It’s not quite time for the big, cozy wool and knitted sweaters at least where I am in Philly. Instead, I’m reaching for the kind of lightweight sweaters you can wear on their own or layer with button ups.

I love a nice cardigan (not going to lie – I wear my folklore cardigan most of the time), cashmere sweaters, and turtleneck pullovers that look nice but literally feel like I’ve thrown on a sweatshirt.

SHOP BELOW

leze the label cardicoat - fall wardrobe essentials

5. That one cozy, oversized sweater

I do think you should have at least one, uber cozy over-sized sweater for this time of year. Think of that sweater that, if you could, you’d turn it into a blanket to cocoon up into on a damp morning.

I was gifted a cardicoat from Lezé the Label, and I’m still obsessed with it (unfortunately they only stock it in an almond color now!). It’s super cozy and I genuinely want to curl up in it half the time. If it wasn’t white, I’d travel with it and use it for planes, but because it’s so oversized and I am so messy, I know it’ll be covered in stains within one trip.

Honestly, another option for those with more casual style is a huge crewneck sweatshirt! When I’m not traveling and just at home or working from home, I cycle through the same like 3 oversized sweatshirts. My favorite is still one I got in college, paint splatters and all.

trench coat - fall wardrobe essentials

6. A lighter jacket or coat

Jacket season, baby! Time to pull out those transitional jackets and let them shine. I, admittedly, might have too many of these… As in I have one of every example below. A part of me wonders if this is a hold over from teaching in Korea where I kept my jacket on the whole day…

Anyway, jackets are such a necessity for fall layering! You don’t want something too heavy because then you’ll be absolutely melting, but you also don’t want something too light or you might as well be wearing no coat at all. They can instantly make a look, and if you’re planning to be outside all day, they’re pretty much the whole outfit.

Coat Ideas:

  • Trench Coat – J.Crew makes fantastic trench coats. (In fact, I heard a rumor they use the same factories as high end designers.) I’ve been using mine for 2 years now and I pull it out every fall and spring. Tan is such a classic color, but if it’s not working with your coloring, try navy or green. Heck, go for a fun color if you know you’re not a neutrals person!
  • Jean Jacket – I still have the same jean jacket from Old Navy that I must’ve gotten 5 years ago at this point. Nothing beats a simple mid-wash jean jacket to throw over dresses. Add patches and pins to customize!
  • Leather Jacket – I inherited my mom’s brown bomber jacket and I love how hefty it is! Honestly, a leather jacket in black or brown will never go out of style, and there are so many ways to wear them.
  • Waxed Jacket – While in Siena, I stopped into a vintage store and picked up a classic Barbour waxed jacket. They really are perfect for those damper fall days when you want something casual but also to keep the wet cold from seeping into your bones! You don’t necessarily need to get Barbour – just search for “waxed jackets.”

7. A darker color purse

I’m not going to lie, my bag usage has gone way down in general. If I’m wearing pants and just running out to dinner, I usually only bring my phone and my card case. This means I can slip them both in my front pocket. However, when I do use a bag, I like smaller ones unless I need to bring my laptop with me.

Here’s What I have:

  • A Crossbody – Pictured above; I had this made in Florence by this lovely artisanal bag designer, Frau Leman. The color is perfect and it fits my kindle! I tend to reach for this when I’m traveling in colder weather and for sightseeing days.
  • A Black Shoulder Bag – Ok, I have two. One from a random Facebook exchange in Vietnam and one from, wait for it, Brandy Melville. I know, I’m shocked too. But it really is such a perfect shape and can be dressed up or down. If I had the money, I’d totally get the Gucci Jackie, the Celine Ava, or YSL Le 5A7.
  • A Tan Structured Bag – I love a nice tan bag because it goes with literally every single color. If you want something more professional looking, you can’t go wrong with any structured bag in tan. Get it in saffiano leather for extra durability. I’ve had the same Michael Kors medium Selma bag since it first came out while I was in college. Seriously, it’s been ten years now, and I don’t think he even makes this style anymore.

8. The Perfect Skirt

There’s just something so stylish about a cute skirt paired with the right top and shoes. I’m partial to shorter skirt with a turtleneck and higher boots. As a someone who is only 5’3″ with a wider frame, I just like how tall I feel with these proportions! If you can’t tell from most of my fall trips last year, this was more or less my uniform. 

For me, the two that work best is my denim wrap skirt (found in a thrift store for $6!) and a plain black mini skirt from Mango. The denim skirt is a little more casual and pairs with all the colors I wouldn’t want to wear with my black mini skirt.

Again, look into what suits your style. I’ve tried longer skirts, slip skirts, pleated skirts, plaid skirts, pleather skirts, skirts with the buttons down the front… These are the two I reach for constantly while the rest have eventually been donated. Though I am planning to get some silk skirts made on my next Vietnam trip…

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RIP to these jeans – lost to the friction of my inner thighs

9. A Quality neutral pair of pants

When it comes to pants, this can go all sorts of ways. Jeans are the most obvious instinct but, you know what, I’m putting a moratorium on any jeans buying for myself. They kind of suck 90% of the time, and I don’t know how we as a society equate them with casual when I find most work trousers are more comfortable!

Anyway, rant over. After finding my perfect pair of mom jeans two years ago and having the thighs wear out while wearing them almost every day in Italy, I decided I would look elsewhere for good pants.

I do still have some jeans in rotation, including a pair from Warp + Weft and an Everlane style I cropped up, but the pants I pretty much lived in all last fall and winter were the paper-bag Haven style of pant from Lezé the Label. They literally feel like wearing sweatpants but look professional and chic enough for everyday wear. I swap out the belt for a leather one to help make it look even more pulled together.

1867 Parkview Inn, Owego, NY

10. Really good boots

I personally find boots to be the ultimate fall shoe! They come in SO many styles these days, there’s something for everyone. Plus, you know, it’s nice for a little extra coverage on the ankles when the wind goes from nice and crisp to harsh and biting.

Some Boot Ideas:

  • Classic Tall Boots – I love a good tall boot, but with an 18-inch calf, I know that 95% of brands are an absolute no-go and the remaining 5% only work because the back is all elastic. Last year I found Duo Boots in my search and if you can’t tell from this post, I wore the Haltham style all fall and winter long!
  • Ankle Boots – Who doesn’t love a good ankle boot? I have a very old, slightly heeled pair from Naturalizer and a Chelsea pair from Nisolo that I wore while in Europe last winter. The nice thing is that while the way they’re styled can change, they themselves will always be a classic buy. Back in the day it was rolled with a skinny jean and now I like wearing them under any straight or wider leg pant.
  • Combat Boots – Okay, this might be a trendier buy, time will tell. Last year I bought these thicker soled boots from DSW to wear with jeans. My friend had them with her cropped pants, and I thought they looked so much better than any other boot you’d want to pair! I reach for them if I’m styling an outfit and something feels proportionally off; they do the trick of correcting it.
  • Cowboy Boots – Y’all, I am so excited because I got got custom-made red cowboy boots (gonna pull. them. off.) this year and I’m just waiting for them to be made! If you like cowboy boots, I don’t think they’re ever particularly trendy or not trendy. They’ve been around for decades and are up to personal tase. I’m getting mine made with awesome Kiwi designer who’s apprenticing in Guthrie, OK named Flora Knight. I’ll share more once I have them!

11. Slip on shoes

The final thing on my fall wardrobe essentials list is a shoe that you can slip on and off easily. These shoes aren’t great for colder days, but work perfectly for those warmer fall days where you just want to be able to get in and out quickly! I feel like these became more essential to me when I lived in Korea and was constantly slipping in and out of shoes going into various schools, houses, and restaurants.

Slip-on Shoe Ideas:

  • Smoking Slippers – I love a good smoking slipper! While I have the Emmeline style from Naturalizer, I really don’t like how the leather crinkles and loses its shape (you can kinda see this above). The ones I’ve been loving the most are my leopard starlings from Birdies. I don’t know what kind of cushion Birdies puts in those shoes, but they feel like little clouds under my feet. If I wanted another leather pair, I’d probably get these from Nisolo.
  • Clogs – I used to wear clogs all the time in school! I was cracking up when they “came back” last year. Honestly, I might buy these in the future because I find Birkenstocks to be the most comfortable shoes that aren’t sneakers, so I imagine I’d reach for the Boston clogs all the time.
  • Ballet Flats in General – If ballet flats work with your style, they really never go out of style regardless of what magazines or fashion blog say. I personally don’t think they work with my proportions or style, but if I were to look into them again I’d, of course, want to try out Chanel’s classic ballet flats or Sarah Flint’s Natalie flats.
  • Mary Janes – I’m really into Mary Jane shoes right now (I made a whole mood board on my Pinterest for them). I think most styles are a bit too feminine for my style, but my friend, Sher, introduced me to Aeyde Uma flats, and I’m in obsessed. I have them saved to try but I also might look into having the custom made if I can’t find ones that work with wide feet.
  • Sneakers – You know when you get a sneaker just right where you never have to untie it and can just slip your foot in and out? That’s what I do to most of mine even though I know it’s probably not good for heel longevity! I prefer white sneakers to black or any other color, and if I don’t reach for my Hokas, I reach for my Vejas. No, they’re not my favorite and the tongue sucks, but I spent too much money on them to not wear them until they fall apart!

And there you have it – all my picks for fall wardrobe essentials! If you have any you’d add, let me know below!

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Fall wardrobe essentials

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3 Comments

  1. Your breakdown of the essential wardrobe pieces, from head to toe, is incredibly thorough and helpful. Thanks for sharing this fantastic resource; you’ve got me all excited to refresh my fall wardrobe with these must-have items! 🧣👢🍁

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