I have a small confession to make: I own more pairs of boots than I do actual seasons to wear them in. My sister teases me about it every single autumn when she comes over and sees the little row of them lined up by my front door like soldiers waiting for orders.
But there is something so satisfying about pulling on a good pair of boots and knowing the rest of the outfit will just fall into place. Boots do a lot of heavy lifting, if you ask me.
So this year I finally sat down and wrote out all the pairings I reach for again and again.
20 Boot Looks I Reach For On Repeat
Chocolate Boots With Knit Dress
There is a particular shade of chocolate brown that makes everything else look richer, and I am fully obsessed with it. Pair a soft chunky knit dress with a pair of chocolate boots and you have a look that feels cozy and put together at the same time.
I wore this to a Sunday lunch last month and my friend Dana asked me twice where the boots were from. That’s how you know an outfit is working.
Black High Boots With Miniskirt
Black high boots with a little miniskirt and yet it never fails me.
Add some opaque tights underneath if the weather has turned, which it always seems to do the moment I decide to wear a skirt. A simple fitted top on top keeps the attention where it should be, which is on those boots climbing up your leg.
Givenchy Boots With Leather Blazer
Okay, so I don’t actually own Givenchy boots, but I have a very convincing pair that a certain retailer sells for a fraction of the price and I will not be telling anyone which retailer because they are MY secret. Pair them with a leather blazer and you look like you have somewhere very important to be.
Even if that important place is the grocery store. Which, for me, it usually is.
White Boots With Denim Midi Skirt
White boots feel a little daring, I know. But paired with a denim midi skirt they suddenly make so much sense. The crisp white against the blue denim is one of those denim and white outfits that just photographs beautifully.
I always feel a bit taller in this one, which I appreciate as someone who is decidedly not tall.
Bootcut Jeans With Pointed Boots
The trick with bootcut jeans is the boot needs a pointed toe to peek out just so. Otherwise the whole thing looks a little clunky and sad, and nobody wants sad jeans.
A pointed boot elongates the leg and makes the bootcut look intentional rather than like something you dug out from 2004. And I say that with love, because I did in fact wear these in 2004.
Hunter Boots With Quilted Jacket
This is my rainy day uniform and I am not ashamed of it. Hunter boots, a quilted jacket, and my favorite pair of jeans tucked in or rolled up, depending on how puddle-y things look outside.
My husband calls this my “country lady” outfit. He is not wrong. I wear it to the farmers market and feel very connected to the earth, or at least to the pumpkins.
Thigh-High Boots With Sweater Dress
Thigh-high boots sound intimidating, but with a slouchy sweater dress they turn into the coziest thing imaginable. The dress covers what needs covering and the boots do the rest.
I keep mine in a low block heel because I am walking, not posing, and my ankles have opinions about anything higher.
Tan Riding Boots With Leggings
The classic. The one that never really goes away no matter what the magazines say. Tan riding boots with leggings and a long tunic sweater is the outfit equivalent of a warm cup of tea.
My mother wore this. I wear this. I suspect my daughter will one day wear this too, and roll her eyes about it, and then keep doing it anyway.
Patent Boots With Pleated Miniskirt
Patent boots have a shine to them that makes everything look a touch more polished. Pair them with a pleated miniskirt and a chunky sweater and you have a look that is playful but still grown up.
The pleats move when you walk. I did not expect to care about that, but I do. It’s a small joy.
Long Boots With Satin Dress
A silky satin dress on its own can feel a little too dressy for daytime. But throw on a pair of long boots and suddenly it reads as something you could actually wear to run errands, or to a lunch that turned into a long afternoon of talking.
The contrast of the soft fabric against the sturdy boot is what makes it. Of course, I always end up spilling something on the satin, but that’s a separate issue entirely.
High Boots With Bermuda Shorts
Bermuda shorts with high boots is one of those combinations I saw on someone else and thought, that will never work for me, and then tried it and immediately loved it. The shorts hit right above the knee and the boots come up just under, leaving the tiniest sliver of leg.
Tailored shorts are best here. Anything too casual and the whole look deflates.
Givenchy Boots With Monochrome Black
An all-black look is my failsafe. When I cannot think, when nothing feels right, when I have five minutes, I reach for black on black on black. And those sneaky designer-look boots pull the entire thing together.
I will not lie to you, I feel very cool in this outfit. Slightly more mysterious than I actually am, which is the goal.
White Boots With Flared Jeans
Flared jeans and white boots have such a retro feel to them, in the best way. The flare skims over the top of the boot and just barely lets it show, which is exactly how I like it.
I found the jeans at a little shop near my sister’s place and bought two pairs because I knew I’d wear them into the ground. And I have. Nearly.
Bootcut Jeans With Suede Boots
Suede boots are a little precious, I admit. You have to baby them and keep them away from rain and mud and life in general. But when paired with a good bootcut jean.
The softness of the suede against the denim is lovely. Just keep a suede brush handy and maybe don’t wear them on the day it decides to pour.
Hunter Boots With Trench Coat
Here’s where the practical boot goes a bit fancy. A trench coat over a simple outfit with Hunter boots underneath is such an easy way to look pulled together on a grey day.
The trench does most of the work, honestly. You could be in pajamas underneath and no one would know. Not that I’ve done that. Recently.
Thigh-High Boots With Blazer Dress
A blazer dress is one of those pieces that looks like a lot but is actually just one thing to throw on. Add thigh-high boots and you have an outfit that could go from a work meeting to dinner without a single change.
I love a single-garment outfit. Less thinking, more coffee, that’s my morning motto.
Brown Boots With Floral Midi Dress
A floral midi dress feels very spring, but pair it with brown boots and it becomes something you can wear well into the cooler months. The boots ground all those pretty flowers and keep it from looking too sweet.
This is my favorite way to hold onto my summer dresses when the weather turns. I refuse to pack them away, so instead I just add boots and pretend it’s still warm out.
Croc Boots With Tailored Shorts
Croc-embossed boots have a texture that catches the eye without being loud about it. Paired with tailored shorts and a fitted knit, the whole outfit feels considered.
I resisted these for the longest time and then caved during a sale, and now I understand. Texture is a quiet way to make an outfit interesting.
Knee-High Boots With Cigarette Jeans
Cigarette jeans have that slim, cropped shape that fits perfectly into a knee-high boot. This is my go-to boots and jeans outfit when I want to look like I tried without actually having tried very hard.
Tuck the hem in, pull the boot up, done. My friend Dana copied this one after seeing me in it, and now we occasionally show up to lunch looking like accidental twins.
Slouchy Boots With Boho Dress
Slouchy boots have that lived-in, gently crumpled look that pairs so well with a flowy boho dress.
I wear this when I want to feel free, which is usually on a weekend when there are absolutely no plans and no reason to be anywhere. Which is my favorite kind of day.
