Boot Guide

While I will gladly press “pause” on my sandals, for now, do any of you stare blindly at your boots each season and think, “Are you still in style? Can I wear you with dresses? Am I supposed to tuck you in or out of my denim?” It’s boot season and while there aren’t TOO many rules as your boots typically stay a bit more classic and traditional each season than, say, a pair of statement sandals, I wanted to create an outfit guide to help you shop your closet. Below, I’ve got six styles you will continually see this season, and outfits to style them all with.

We’ve got tall boots {think knee high}, over-the-knee boots {yes, still in style}, flat booties {tried and true for comfort}, heeled booties {date night!}, combat boots, and western/cowboy boots {not just a trend to us Texans. 😉 }. Grab an iced tea, take this post on your phone, and go shop your closet this weekend. I hope this helps you pull together some looks in your closet you may have not been thinking about!

Sweater | Hat | Turtleneck | Bag | Boots

A boot getting much more love this year is the tall boot. In years past it was ALL about over-the-knee options, and now you can bust out those that just hit the knee. While riding boots are classic, they aren’t as trendy, and these are different. This season’s tall boots are heeled, usually have textured leather, and hit right under the knee. Wear them with your skinny jeans and a duster coat like above, or with dresses as you see below. I think this is the new go-to with a sweater dress, instead of just over-the-knee suede boots.

Dress, Similar | Bag | Hoops | Bracelet | Boots

On Friday Q&A’s the top “boot” related question as of late, “Are over-the-knee boots still in style?” 100%! In fact, my Stuart Weitzman Lowlands are probably the best shoe purchase I’ve ever made in terms of cost per wear. I bought them seven years ago, have worn them everywhere from Fashion Week to the farmer’s market, and they still look brand new. I think we often think styles aren’t as popular when we don’t see “dupes” of them as frequently. The same goes for Golden Goose sneakers. GG sneakers have been around since 2007, with popularity in these styles spiking in 2018. They are trendier, but they aren’t leaving shelves anytime soon. We just may not be seeing dupes as prevalent and the same goes for over-the-knee boots, simply because you’re going to see that with more current trends, like the western boot. And while over-the-knee boots to GG sneakers is like comparing apples to oranges, you can feel safe knowing a traditional over-the-knee suede boot like Stuart Weitzman is here to stay. Our comfort zone may be skinny jeans {as seen below} but I wanted to share the above look because I think they are amazing with a neutral-toned dress. When you want something in your closet to feel fresh, style it with a different silhouette or look than you typically do.

Dress | Boots | Headband | Bag | Bracelet

Booties are usually the trickiest in terms of styling, as people get torn on “to tuck or not tuck” the denim. I’ve tried many types of flat booties, and personally, I prefer a low shaft. The tall ones feel like they’ll rub the skin on my ankle raw and as a shorter gal, they don’t lengthen my legs. {The “tunic” look here features a taller shaft. I have a few I like, but I don’t love them.} I usually keep my denim more cropped, so with a shorter shaft, you don’t have to worry about tucking or not tucking as my denim hem usually just kisses the top of the shaft. What about if you have a taller shaft? If you have straight-leg or relaxed denim, I would avoid cuffing them if they aren’t short enough. Just let them graze over the bootie. If you have skinny jeans, tuck inside out, as I think the rolled denim look with booties is a bit more dated. I shared a few dress looks as this is what I usually wear to church in the fall, and it’s best for me to carry my babies with!

Dress | Booties | Bag | Jacket

For a date night look, you can’t go wrong with these studded beauties. They run TTS {you could size up if you want them to have a bit more room, I didn’t}, have a rubber sole to protect against wear, and add a touch of edge to any girly dress. These have a tighter shaft, so I’d reserve them for cropped denim or a dress. I don’t know that I’d tuck skinny jeans into them, as it may just seem a bit forced. I wore these to a concert and got so many compliments, truly have never had more comments about a shoe I have owned!

Sweater | Spanx {KATEYXSPANX for discount} | Boots | Backpack | Headband

Combat boots were quite on trend last year and I kept thinking, “No way. No how. Not for me.” They were too cool for me and I just felt like I couldn’t style them. That is, until I found a pearl pair during Thanksgiving week and fell in love. I use them to soften up leather leggings or add a bit of sass to a girly look. Pair tights with your ultra-feminine dresses {like below!} and style them with combat boots. I don’t know if I would love them as much with denim on me, but they have been the perfect addition to leather leggings as the size of combat boots plays well with more fitted pants. It’s a nice juxtaposition! One part sleek and one part statement.

Dress | Boots | Bag | Earrings | Bracelet

All my Texas girls have been LIVING for this moment for western boots to be on-trend, because this is what we wear for a Saturday night out anyways. Pair them with skinny jeans, feminine dresses, and flirty skirts. Aside from wide-leg crops, and 90s denim, I can’t think of an option you couldn’t wear these with. PLUS, you can wear them all year, unlike over-the-knee suede boots. 😉 We wear them with our Sunday best, but you can wear them any dress in your closet- I promise! If a tall western boot isn’t your jam, there are plenty of bootie options this fall and winter like these.

I hope this post helps you gather some new inspiration for your fall wardrobe! Which boot or bootie is your favorite style?

P.S. Thank you for your patience on gift guides- they are coming, I promise. This week I have been focusing on some family matters and wasn’t able to get those live. Thank you for understanding. 

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  1. Shannon wrote:

    So excited for boot season! Thank you for the guide! I’ve had my eye on the Stuart Weitzman Lowlands for a few years now and I love the pearl combat boots!

    Published 15 Oct 21Reply
    • Katey wrote:

      Thank you so much for reading!! Xx, K

      Published 15 Oct 21Reply
  2. Annaliese wrote:

    You always give me such good inspo for boots!! So many fun fall fashion options here. I just got a new pair of tan suede boots in the Nordstrom Sale this summer that I’m excited about!!

    xoxo A

    Published 19 Oct 21Reply