Are you a shoes or bag girl? I think in my core I’m a bag girl, but I do love my shoes! I sadly just don’t get to wear a ton of them in Chicago once the weather turns colder. Rain, sleet, snow and dirty Chicago streets don’t equate to pulling out the designer shoes unfortunately. But, I have found that there are some styles I consistently reach for every year for Fall that I get a ton of wear in before the colder temps set in and I’ll tell you why!

SAM EDELMAN LORRAINE BIT LOAFER

I first purchased this shoe in 2017 and have been obsessed ever since. I own them in silver, black, white and am looking to get these soon! They are the perfect shoe to run around in and I wear them most often to work. They are so comfortable and add elegance and polish to any look from ripped jeans and sweater to slacks and a button down if you work in corporate. They come in every color imaginable and different materials from suede, leather and patent leather and crocodile (faux). I’m very true to size in Sam Edelman and go with my normal size of 7 - they do stretch out a bit over time, but this only makes them more comfortable and shouldn’t impact sizing. I also get asked a lot if they are the Gucci pair - such a great dupe!

BLOCK HEEL BROWN BOOTIES

For the last few years I’ve been on the search for a pair of brown block heel booties that didn’t break the bank. Unfortunately, two winters ago I was wearing a pair and running to catch the bus (like really running) and the seam of the bootie completely split open when I fell on some ice (as you can imagine IT WAS A DAY). Since then I hadn’t been able to find a pair that weren’t an investment that I loved. While browsing some sites I came across these. I didn’t want true cognac, the heel height had to be right and they needed to be affordable. Well they came in last week and I love them! They are comfortable (took about two days to break in the stiffness) and I love the added height - and they’re 37% off!

STEVE MADDEN GEORGETTE OVER THE KNEE BOOTS

I’m sure y’all are familiar with this style as they’ve been all the range the last few years. I first ordered a pair that had a taller heel and since I’m somewhat tall and long legged I was just getting stripper vibes every time I wore them, which for me was not the goal. I then discovered the Georgette style from Steve Madden and love them! I have them in black and a taupe / grey color and they are easily one of my most worn shoes in Fall and Winter. Pair with skinny jeans, leggings, a long midi dress, skirt and sweater - the options are endless. These are tight enough to stay up on your leg, comfortable and the colors are great.

PERFECT COMFORTABLE PUMPS

I love wearing heels, but not all heels are created equal. The majority of the amazing ones are very uncomfortable and the comfortable ones aren’t the most exciting usually. When I was working in investment banking, I was wearing heels almost everyday and found my go-to pair that are stylish and comfortable. The Sam Edelman Hazel Pump. They come in a ton of colors, suede or leather, are the perfect heel height and very comfortable! I love the suede as they are a bit more formal and great for Fall and Winter, but I own a nude pair in leather and love them too! They come in a leopard brahma that I will be buying myself!

CASUAL SNEAKERS

In today’s trend world, it seems sneakers are here to stay. I’ve been a more athleisure / Nike girl when it comes to sneakers and I wasn’t loving the Golden Goose dirty sneaker vibe that everyone was into. I couldn’t justify spending THAT much on sneakers that looked they had been in the back of your closet for 10 years… so I opted for some dupes that weren’t as distressed and they did not disappoint! I ordered these from SHEIN to give the trend a try and really like them! I pair mine with jeans and even dresses for a more casual look. I’ve added some other styles below, but if you order from SHEIN I would go up a size!

SNAKE SKIN

Leopard is very in this season and so is snake skin! Really any animal print, but one I am loving with neutrals is snake skin. From booties, to slides to pumps, I look the way it adds some edge to your look that is a bit more understated than leopard. I got these Sam Edelman booties last Christmas and love them! Paired with jeans and even shorts if it’s still warm where you are, they are a low heel and pretty comfortable - they are a thick material so breaking in takes a bit. One of my favorite pairs of shoes were a gift from Kollin and he totally surprised me with - you guessed it - snake skin! They are an older style, but are similar to these!

Mules

Similar to the loafers at the top of the post, the mule loafer style was all the rage when Gucci made them in every color, with fur, and multiple designs. While they won’t transition you into winter, they are an easy, on-the-go style that you can wear throughout the Fall season. I love this pair, but have added some cheaper options below too!

BLACK BOOTIES

Always a classic and always chic, black booties will be a closet staple for years for come. I prefer a black heel for comfort, but love a stiletto black bootie too! My favorite pair are shocker, Sam Edeleman Hilty Pointed Toe Bootie, but I’ve linked some other amazing ones too! Pair these wth a pair of skinny black denim or even leather leggings for a date night and wear more casually with a cute sweater and skirt during the day.