My Favorite Fall Shoes and Boots

Last weekend, I had some downtime on Sunday afternoon, and I went through my closet and weeded out items I’m not wearing, as well as anything leftover from my summer wardrobe that I was hanging onto for those occasional mild days.

I thought it might be fun to recap what’s left, or at least my favorites in each category, so these are my favorite fall shoes and boots.

These are mostly items I’ve purchased this year because I tried to keep this list to things that are currently available, in case you’re interested in any of them, but it’s also meant to be something of a fall footwear capsule.

In other words, these are the types of shoes and boots I find myself needing each year. The styles may change, but the types of footwear tend to carry over from year to year. Maybe it will be helpful if you’re tweaking or finalizing your fall wardrobe.

My Favorite Fall Sneakers

I live a casual lifestyle, so stylish sneakers are a must, and I have several pairs I reach for on the regular.

P448 John Sneaker

My P448 Johns from this year’s #NSale are probably my most-worn pair at the moment. They’re so easy to slip on and go, they’re super comfortable, and I love the gunmetal accent on the back.

These sneakers are pricey, so I always buy mine when they go on sale. You can read more about why I think they’re worth the price. I wear them with everything from dresses and skirts to jeans and shorts.

Caslon sweater dress // AG Mari jeansTreasure & Bond sweater

J.Crew Field Sneaker

For a more affordable option, the newest addition to my sneaker wardrobe is the J.Crew Field Sneaker. I love this low profile style; it reminds me of the Adidas Samba that’s so popular right now, but I like that it’s not the exact same shoe. Also, these sneakers are 30% off right now, with code SHOPNOW.

MOTHER Tomcat // J.Crew Field Sneaker (30% off)

I usually wear these with my slim straight ankle jeans, like the MOTHER Dazzler.

Caslon thermal // MOTHER jeans (on sale) // J.Crew Field Sneaker (30% off)

I like it best when there’s a break between the jeans and the top of the shoe, but it also works when the jeans are a little longer, like with the Gap Factory straight leg jeans below.

Gap Factory straight leg jeans ($29) // thermal top ($12) // puffer vest ($29) // J.Crew Field Sneaker (30% off)

My Favorite Fall Boots

If I’m not wearing sneakers in the fall, I’m probably wearing ankle boots, so I like to have several different styles and colors. In fact, I have two shelves of ankle boots in my closet right now.

Over the past few years, suede booties were a huge trend, but I’m feeling like leather looks fresher and more current this season, so that’s mostly what I have right now.

Marc Fisher Fabina

Marc Fisher Fabina // AG Mari slim straight ankle jeans (on sale)

I always make sure to have at least one pair of black ankle boots in my fall/winter closet, and they get a lot of wear, so I often have a few styles.

The Marc Fisher Fabina Pointed Toe Bootie is the newest addition to my fall shoe wardrobe, and it’s a nice versatile style that you can dress up or down. If you don’t need a lot of boots, this is a pair that you can wear with lots of different outfits.

I’ve worn these boots with straight leg jeans, flares, and wide leg jeans, and they look equally good with all of them. The 2 1/2″ block heel is walkable and still gives me the height I need with longer length  jeans.

Rails stripe cardigan & AG jeans // LOFT dress // bomber jacket & MOTHER Roller

These boots aren’t “waterproof” but the leather is hard and shiny enough to withstand messy Pennsylvania winters. If I could have only one pair of black boots, it would be this pair. And if you aren’t into black, these also come in brown and white, and the brown pair is especially beautiful.

Marc Fisher Ulani

When I want a dressier look, I usually opt for the Marc Fisher Ulani, which I purchased during the #NSale last summer. I realize these are awfully similar to the Marc Fisher Fabina, but they have a slightly higher heel and an overall dressier look about them. The Fabina has a bit of a Western flair with the tapered heel and slightly squared off toe box, but the Ulani is more of a dress boot.

Marc Fisher Ulani Pointy Toe Bootie

I usually wear this pair with dresses, when I want to wear ankle boots with a dress, but they also look great with bootcut jeans and a pretty blouse when I want a date night look.

These boots have a 3 1/4″ curved half moon block heel and a 5″ shaft, and they’re made of a sleek and soft black leather. (They also come in black suede and ivory leather. Also, if you want a similar style in a lower heel, take a look at the Marc Fisher Jarli.)

Open Edit dress // Vince blouse // PAIGE flare jeans // Treasure & Bond bomber

Vince Hilda

I also purchased the Vince Hilda Bootie during the #NSale last summer, and I love the lower heel and the sleek almond shaped toe. Plus, the leather on these boots is like butter. They are absolutely gorgeous.

Vince Hilda (similar option on sale) // Gap Factory jeans

I don’t really need these, in addition to the other two, but I do love them. I find myself reaching for them when I want a softer, more luxe (and also low heel) boot option. The 1 3/4″ heel is refreshing to wear after years of 3 3/4″ heels!

Since the leather is so soft and supple, I’m more careful with them than I am the two above and probably won’t wear them in messy weather.

Talbots sweater & jeans c/o // BR ribbed top & MOTHER jeans // Gap Factory sweater & jeans

Nordstrom Rack has the Vince Hela on sale, and it’s very similar, but not quite as soft. Still, it’s a great price for Vince boots, so if you can find your size, I would recommend going with that pair.

Blondo Sadie Waterproof Bootie

I also want to include the Blondo Sadie in this list because I like to have a waterproof suede bootie in my fall/winter closet. Even though I feel like smooth leather looks more current, these are still a nice option to have, and this pair is very comfortable.

Blondo Sadie // Vince sweater & MOTHER Roller // Gap Factory sweater & black flares

Dolce Vita Volli Western Boots

While I thought they were going to be passé this season, the Western style is still trending, and I love the Dolce Vita Volli for more of a rugged, casual look.

Mine are from last year, and I have both Dune and Brown, but the Brown is the only pair I’ve worn so far this season. I still like the Dune, but I feel like darker browns are more on trend right now.

Dolce Vita Volli in Dune

Nordstrom Rack has the Dune color (pictured above) and Evereve has a very similar pair to my Chocolate Brown (pictured below). I like how Evereve shows you styling options.

These boots look great with flares, and they work with straight and wide leg jeans, as well.

Rails sweater (on sale) // BR jeans // similar boots

Tory Burch Chelsea Boots

You might have noticed that most of the boots above have a heel, and last winter, I found myself wanting a pair of flat ankle boots that I could wear when I wanted to do a lot of walking, or just wanted a more casual vibe.

I ended up with a pair of Tory Burch Chelsea boots very similar to this pair. I do like them, and the quality is impressive, but they sometimes feel a little too masculine for my personal taste.

Here’s how they look styled with bootcut jeans. I wore this outfit to meet a friend for lunch on a rainy day a few weeks ago.

Gap sweater (S) // MOTHER jeans (on sale!) // AllSaints bag (sold out)

These are staying in my closet for now, but I have another pair of Chelsea boots with more of a rounded toe that I recently added to my closet…

Steve Madden Leopold Chelsea Boots

I find myself reaching for this Steve Madden pair when I want a flat black leather boot that can withstand inclement weather. The glossy leather is extremely durable and keeps your feet dry, while the lug sole provides great traction on wet pavement.

Steve Madden Leopold Chelsea Boots // AG jeans

Even though they aren’t as nice of a quality as the Tory Burch pair, they’re similarly comfortable, and the rounded toe feels a little more comfortable to me.

These booties look best with longer jeans, like these AG Mari straight ankle jeans (currently on sale at Bloomies). When I tried them with a shorter inseam, they looked rather awkward.

AG Mari jeans // Helly Hansen rain coat (M) // Treasure & Bond sweater (S) // Madewell bucket bag

Paul Green Selma Lug Sole Bootie

When I want a more rugged, casual look, I enjoy having a pair of lug sole booties in my fall/winter wardrobe, and this year my go-to is the Paul Green Selma from the #NSale. These are a major splurge, but they are back on sale at Nordstrom Rack.

These boots are soooo comfortable, and I love the shade of brown. It works well with so many of the neutrals in my closet.

I wear them with all styles of denim, but I think I like them best with straight leg styles. I feel like my bootcut and wide leg jeans look better with more of a pointed toe, but I do make exceptions depending on what else I’m wearing.

Paul Green Selma // green henley & MOTHER flares // ivory sweater & PAIGE wide leg ankle jeans // brown puffer & straight leg jeans

If I do wear the lug sole boots with a wider leg jean, I think I like them better with the ankle-length style, so you can see more of the shoe.

Blondo Skara

Knee-high boots are trending big this fall, and I especially love these with skirts. I recently added the Blondo Skara Waterproof Boot in chocolate brown to my fall wardrobe, and they’ve come in very useful already.

For one thing, these boots are incredibly comfortable to walk in, but they also are waterproof so I can look elevated even when the weather is messy.

I chose brown because I already have a pair of black knee boots, but they’re still packed away in the basement. I guess I need to retrieve them!

I also really love the Sam Edelman Shale in the Caramel, but sizes are very picked over at this point.

Sam Edelman Shale (size 8) // Eliza J sweater dress (size L)

Other Fall Shoes

On the rare occasions that I’m not wearing boots or sneakers in the fall, I usually opt for loafers or clogs, although I’m glad to see ballet flats making a comeback this year!

Kork-Ease Clogs

I have the Kork-Ease Sudbury Clogs in both brown leather and taupe suede, and I also still have my Kork-Ease Darby Clogs from last year.

Kork-Ease Darby Clogs

I actually end up wearing the Darby clogs more because the back strap makes them easier to walk in, although I don’t really have trouble keeping the Sudbury clogs on my feet.

Kork-Ease Darby // Good American straight ankle jeans

My biggest issue with the Sudbury is my pant leg tends to get caught under my heel when I wear longer length jeans. I feel like clogs work better with ankle-length styles.

Kork-Ease Sudbury // ivory sweater & brown cords // oatmeal sweater & MOTHER Roller

Loafers & Ballet Flats

For flat options, I love my Gucci loafers, but the price has gone waaaaay up since I purchased mine, and the Sam Edelman Loraine is very similar for a fraction of the price. I’ve tried them, and they’re comfortable too.

similar loafers // stripe sweater on sale at Shopbop & Bloomies // old Fidelity denim

I just purchased and started wearing the Marc Fisher Ubet Ballet Flats in the brown, and I really like the squared-off toe and more structured footbed. Unfortunately, they’re getting harder to find fully stocked. They’re currently on sale at Bloomingdale’s, and they’re also available (but low inventory) at Nordstrom.

Marc Fisher Ubet (on sale) // Talbots sweater (30% off) // MOTHER denim (on sale)

Favorite Heels for Fall

For my last category, I like to have a few pairs of heels for dressier occasions.

Vince Camuto Frasper Bootie

An open toe bootie like the Vince Camuto Frasper is really fun to have. I’m not seeing this as a big trend right now, but I do really like this pair.

Vince Camuto Frasper Bootie (other color options)

I especially like them in this taupe color because it blends in with my skin tone, which elongates the line of the leg.

Vince Camuto Frasper // LOFT dress

That color only seems to be available at Evereve, though, and I also like the brown and black options at Nordstrom and Zappos. They would look especially good with jeans.

Vince Camuto Frasper // Vince blouse (on sale) // PAIGE denim (on sale)

Marc Fisher Varla Block Heel Pump

Finally, when I need a closed-toe option, I love a good pair of pumps, and the Marc Fisher Varla Block Heel Pumps are gorgeous.

They look nice with trousers for work wear or other conservative events, they pair well with dresses, and they also look great with flare-leg jeans when you want to elevate your denim.

leather jacket & PAIGE denim // Eliza J dress // plaid pants & burgundy sweater

Well, that definitely went longer than I expected! I think this should about cover just about any fall shoe I might need in my fall and winter wardrobe.

Which styles are you loving right now?

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12 Responses

  1. Great post. I was smiling a bit as you explained the differences between the first four or so pairs of black ankle boots, as it reminded me of myself 🙂 My mother has never been much of a fashionista and would often say something like “but you already have black heels” when I wanted to purchase another pair. Then, teenage me would have to explain why the pair I was looking at was COMPLETELY different. Haha! Anyway, these are all gorgeous shoes. I have the Sam Edelman Loraine loafers in a cognac/tan color and have been wearing them a lot. I would like to get them in black too but have to wait until next month as I’ve already spent this month’s clothing budget. Have a great rest of your day!

    1. Yeah, maybe for the purposes of this post, I should have just picked the one most versatile pair of black leather boots… I really could get away with just the first pair and the Madden Chelsea boots. I think. But I do sometimes want a dressier style… so now we’re back to at least three pairs. Haha! Six is probably excessive. I do wear them all, though. 🙂

  2. I’ve had a tall suede boot on my list for sometime now but just haven’t found the right ones! I love the ones you’ve styled! We are heading to Maine and New Hampshire in a week and a half so I’m going to look ! DSW there tends to carry more high end than ours here in Canada! I have several l Pairs but the suede would be nice before the real messy weather comes and be great with dresses and skirts on Sunday!
    I purchased a pair of black leather Chelsea boots last year at Banana Republic and wore them much more than I thought! They are super comfortable and don’t feel like a big manly boot on!!
    I tend to keep the suede booties with a heel for Sunday’s or occasions out! Daily errands and shopping etc I like my fashion sneakers or the Chelsea boots!
    Based on this post I’m due for a few more lol

  3. I don’t think you can have too many pairs of black booties. I have four and they are all slightly different. I’m trying to not buy more though. I’m on the hunt for the perfect pair of chocolate brown booties. I have a pair in suede but think smooth leather is a touch more elegant.
    I thought open toe booties were not on trend. 🤔 Although the pair you show are beautiful.

  4. Love the 3/4 sleeve teal dress with those brown colored tall boots. Do you think the over the knee boots will have a comeback, never had a pair but would like to try. Can you share details on that teal dress? All of these outfits look great on you and I think the T&B black leather bomber really looks nice on you, love the sort of oversized look.

  5. Thanks for giving the details on these boots, as it makes me feel more confident in ordering online. Do you have any recommendations for winter snow boots for actually wearing in the snow? No ski bunny here, but I need to replace a pair for winter dog walking, shoveling, etc. and there wasn’t much available last season. Thank you!

  6. I like the brown suede Blonde boots. I wish you would show a side view so I could see the circumference. Most tall boots are made so wide nowadays. I have skinny calves so most tall boots look like I’m wearing my father’s rain boots. The site says circumference is 14 inches and shaft is 14 inches. Would you say that it’s true.

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