A great pair of shoes can make an outfit and can also affect your day. When I pick a pair, I’m looking for comfort, versatility, and durability. I want a pair that’s going to last and also look beautiful wear after wear. I personally believe in quality over quantity, and my own collection of shoes is only a little larger than typical because I write about and style clothes for a living. So, I’ll go ahead and say first, this post is in no way saying you should own every single one of these or need them all to complete your wardrobe. Instead, I’m going to highlight different options and the ways I wear them so you can choose the best pair for you and your style! Bonus, if you have a smaller foot like me, all of these fit a size five (some start at 5.5 and run small) and some under a size five.
Booties
Marc Fisher Alva Bootie
I bought these booties last year and they became my most worn pair. They’re a great everyday pair of boots that look great with a large variety of jeans, skirts, and dresses. I bought them in both brown and black, but I wear the brown pair the most. They are expensive, but I can attest to their quality. They also go on sale from time to time and I try to keep an eye on that and let you know in my Instagram story. They have great structure and haven’t stretched or wrinkled with wear. I sized up to a size 5.5 in them per review. I tend to like a little room in booties in general and these fit me with a little room. These boots also come in a wide variety of colors to match your style.
Pros: Durable, neutral and nicely structured.
Cons: None
Comfort Level: Moderate, I can wear these for an entire day, but they do have a high heel that can be uncomfortable if you’ll be doing a lot of walking and standing.
Price: $$$
Ways to Wear Alva Booties
Although these boots work with skinny and straight denim, as well as dresses and skirts – I wear these boots mostly with skinny jeans. The shaft comes up high enough to meet the hem of most of my skinny jeans, but it’s also a little wide and looks heavier with straight jeans. If your wardrobe is mostly straight jeans, you may prefer one of the pairs below.
Boots Size 5.5 Size Up 1/2 Size | Skinny Jeans 0 X-Short | Straight Jeans 25 Extra Short | Red Top XS | White Top XS | Cardigan XS | Moto Jacket XXS | Dress Petite XXS | Belt | Necklace | Necklace
Welland Bootie
I appreciate the slim profile of this pair. The heel is still thick enough to keep the boots comfortable, but slim enough that they feel slightly less clunky. I also like the neutral taupe color. However, this boot is softer and the shaft has already started to wrinkle and look a little floppy despite only a few wears. The Welland Bootie runs small, I sized up 1/2 size.
Pros: Nice neutral color and slim profile that works well with a variety of jeans. This pair starts at a size 5 but runs 1/2 size small so may fit you if you’re a 4.5.
Cons: Leather is soft and the shaft wrinkle easily.
Comfort: Moderate
Price: $ (on sale often)
Ways to Wear Welland Booties
Another benefit of these boots is their versatility. The slim shaft works well with a variety of jeans and also looks great with dresses and skirts.
Boots Size Up 1/2 Size | Skinny Jeans 0 X-Short | Straight Jeans 25 Extra Short | Skirt XS | White Sweater XS | White Sweatshirt Tunic XXS
Steve Madden Calabria
If you’re looking for a bootie that goes great with straight jeans, these are it! They have a sleek and slim shaft that helps add a little balance to a straight leg. They also look great with dresses and skirts. I recently bought the black pair and went back for the tan pair after seeing how great they looked with straight-leg jeans. I bought these in a 5.5 and they fit me with a little room. The heel is also not crazy high making them a little more comfortable to walk in.
Pros: Sleek shaft that looks great with straight jeans, moderately priced.
Cons: They don’t pair as well with skinny jeans.
Comfort: Moderate
Price: $$
Ways to Wear Calabria Booties
The Calabria Booties look great with straight jeans, demi-boot jeans, skirts, and dresses.
Boots 5.5 | Straight Jeans 25 Extra Short | Belt | Moto Jacket XXS (similar) | Charcoal Jeans Petite 25 | Skirt XXS | Mockneck Top XS
Target Kennedy Booties
If you’re looking to add a printed bootie to your wardrobe, I recommend this affordable pair from Target. The Kennedy Booties have a lower heel and a memory foam footbed. However, the shaft rubs my ankles which makes them a little less comfortable. Since I don’t get a ton of wear from a printed bootie I didn’t want to spend a lot of money on them. This pair is just right in the price department. I wear them in a size 5 and they have a little bit of room so I would say they run a little bit large.
Pros: Affordable, lower, walkable heel.
Cons: Rubs the ankles, but may improve with wear.
Comfort: The heel height is comfortable, but they rub on the ankles a little bit.
Price: $
Ways to Wear Kennedy Booties
These booties have a lower shaft which makes them an easy match to most jean styles as well as dresses and skirts. They give an overall casual look to the outfit.
Boots 5 | Skinny Jeans 0 X-Short | Straight Jeans 25 Extra Short | Red Top XS | Moto Jacket XXS | Skirt 00 | Necklace | Necklace
Other Ankle Boots
I’ve been searching for a pair of combat and Chelsea style boots I like so I will be back to update this post once I find a pair I love. In the meantime, here are a few I’ve ordered, two of which are great for rain (the wedge boot) and winter weather (the sherpa boots). I’m also sharing all of the boots from above and other lower-heel options through this slide.
Knee High Boots
I love having a pair of knee high boots on hand to wear with leggings, skirts and dresses. Both of the pairs I’ve found and love have a western twist to them, which is one of the trends this season.
Vince Camuto Afelia Boots
First, the Afelia boots! I don’t really have a favorite between the two pairs I have, I really like them both equally. The difference between both is the price and the height of the shaft. The Afelia pair is more expensive but is also a little dressier than the pair I’ll share next. They come up to my knee and they have a slimmer shaft that isn’t too overwhelming on someone who is petite. They’re very comfortable and walkable and I find them to be true to size in a size five.
Pros: Comfortable, dresses up an outfit, comes in multiple colors.
Cons: None
Comfort: Walkable and comfortable
Price: $$$
Ways to Wear Afelia Boots
I will mostly wear these boots with leggings, skirts and dresses.
Boots 5 | Leather Leggings Petite XS | White Sweater XS | Shacket XS | Chevron Sweater XS | Plaid Skirt XS
Target Adeline Boots
These boots are my favorite to wear! They’re so comfortable and have been the pair I’ve been reaching for (if the weather is cool enough) when I just want to be comfortable. I wear them with leggings and skinny jeans mostly, but they also work with skirts and dresses if you want to go for a more casual look. They resemble a cowboy boot and the shaft comes up to a couple of inches below my knee. They’re true to size and I wear them in a size five.
Pros: Affordable, versatile and comfortable.
Cons: None
Comfort: Max comfort.
Price: $
Ways to Wear Adeline Boots
I’ve been wearing these boots mostly with leggings and skinny jeans, but they will also work well with casual dresses and skirts.
Boots 5 | Red Top XS | Skirt 00 | Leggings XS Short | Charcoal Jeans Petite 25 | Flannel Top XS | Sweater (middle) XS
Over The Knee Boots
I’m still searching for a pair of over-the-knee boots I like. It’s partly the height that I don’t like, but it’s also the tightness on my thighs that bugs me. So I’ll update this when I find a good pair. In the meantime, you may like this pair:
Flats
I have a few pairs of flat shoes but there are two styles that I wear the most (and that are still fully stocked). I wear flats often during the transitional season when it’s cooling off, but not yet cold enough for boots all day long. I also wear flats to work all season long.
Rothy’s
Rothy’s are new to me this year, but they’ve become my new favorite. I have the classic point in both black and camel. They’re slightly stretchy, but they do run a little small so I would recommend sizing up 1/2 size. They’re comfortable for all-day wear and they’re washable! They are a little expensive, but the ability to wash them (which I haven’t tried yet) should make them an investment shoe that will last for years. I mostly wear them with skinny jeans or straight jeans. I also wear them with dress pants for work and with skirts.
Pros: Comfortable, versatile, and durable classic style that will last in your wardrobe for years. They also come in a variety of colors and prints.
Cons: None
Comfort: Walkable and comfortable.
Price: $$
Ways to Wear Rothy’s
I often wear Rothy’s to work with dress pants and skirts. I also wear them with both skinny and straight jeans.
Rothy’s 5.5 | White Pants 25 Petite | White Top XS | Jeans Petite 24 | Purse | Moto Jacket XXS | Mockneck Top XS | Wrap | Burgundy Sweater XS
Steve Madden Faraway Mules
Steve Madden puts out a variation of this mule every year. I have last year’s version that has a smaller chain across the front. My version is still available in many places including Amazon and Nordstrom. They’re comfortable and easy to wear all day, but I have heard from some of my readers that their foot was too narrow for them and they felt like they were walking out of them. So, if your foot is narrow they may not be the shoe for you. I have them in both black and nude and prefer to wear these with dress pants and skinny jeans. I’m wearing them in a size 5.5 which is the size they start at. You can see them styled with multiple outfits in my recent capsule wardrobe post.
Pros: Comfortable and great for dressing up an outfit.
Cons: May not be best for someone with narrow feet, they also don’t work well when the weather cools off.
Comfort: I find them to be great for all-day wear.
Price: $
Ways to Wear Faraway Mules
I wear them mostly with dress pants and skinny jeans, but they also work with straight jeans. They don’t elongate the legs as well as a style like the point, so that may be another deciding factor for you.
Mules 5.5 | White Sweater XS | Jeans Petite 24 | Sweater XS | Skinny Jeans Petite 24 | Floral Top Petite XXS
Other Flats
I also love to wear these leopard loafers, but they are limited in stock which is why I didn’t include a full write-up about them. But, if you’re able to snag your size they’re comfortable and great for adding something to a neutral outfit.
Heels
In the fall and winter, I’m less likely to wear heels other than dressing up an outfit for work, church or a special occasion. Year-round I found the Hazel pumps from Sam Edelman to be a great option in terms of sizing. They even start at a size four. However, my top choice for versatility and beautiful color is the Azra pumps from Ann Taylor.
Azra Pumps
The Azra pumps are a beautiful dark tan suede that blends beautifully with most skin tones. They have a leg elongated pointed toe and the heel isn’t so high that you can’t walk in them for extended periods. They do run a little large. I have them in a size five and they have a little room on me, my feet tend to heat up and swell a little in pumps which makes it so I can keep these on, but I want to be transparent with you about them being a little large. If you’re able to I would size down 1/2 size in them for a great fit. They often go on sale, up to 50% off, so I would keep an eye out for that to get a great deal!
Pros: Beautiful neutral color.
Cons: Runs a little large.
Comfort: In terms of a high heel, this is a comfortable pair.
Price: $ (on sale)
Ways to Wear Azra Pumps
The Azra pumps look great with everything from jeans to dresses and skirts. They dress up any outfit and elongate your legs.
Pumps Size Down 1/2 Size | White Pants Petite 25 | Belt | Moto Jacket XXS | White Sweater XS | Cream Skirt XS (needs a slip under it) | Pleated Skirt XS | Blazer Petite 00
I hope you find a pair of fall shoes to love, that fits your style from this post! I’ll be updating you when I find other great options!
-Brooke
