The Best Tall Boots To Wear With Dresses

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If there’s one outfit combination that feels especially timeless, especially as denim silhouettes swing wildly between skinny, flare, mom jeans, cropped…it’s wearing tall boots with a dress or skirt. Not only is this outfit combo easy to pull off — seriously, a dress + tall boots always looks great — but it hits that elusive note of comfortable sophistication.

Tall boots and a dress is one easy answer when I want to look effortlessly put-together…but jeans aren’t quite appropriate. Or when it’s still a little too warm for jeans and a sweater. And heck — it’s a combo that works into any sort of day-to-night rotation.

But which pair of tall boots work the best with dresses and skirts?

Unsurprisingly, I have strong opinions.

Over the years, I’ve found myself reaching for the same few pairs of tall boots whether I’m wearing a mini, maxi, or midi-length skirt or dress. And almost every darn time, it’s one of my favorite pair of vintage Frye boots.

Over the last — oh geez — 20 years or so, I’ve been the lucky recipient of two pairs of vintage Frye’s. The darker, reddish ones are now in pretty rough shape, but they were literally bought in the ’70s…and have been well-worn, much-used and very loved.

But what makes these particular boots special? Why are they so timeless (I’d seriously wear either of these outfits today), and why do these boots go so well with all of the dresses or skirts?

The Best Knee-High Boots To Wear With Dresses & Skirts This Season

First, and perhaps most importantly, I look for a tall boot with an uncomplicated, clean, almost vintage style. If it’s vaguely reminiscent of a boot that an English soldier may have worn in the 1800s, AND maybe your mother also wore something like it in the ’60s…that’s my favorite boot. The toe is not quite rounded, but not pointed, either. The heel is walkable and sturdy; neither stiletto nor wedge.

Secondly, I’ve found (after years of styling) that a rich tan (or caramel) is simply easier to style. There’s absolutely nothing wrong with black, it’s just that some outfits can be overpowered by black boots, but almost all outfits will look good with rich tan, burgundy, or camel boots. I consider these colors to be pretty foolproof (even with otherwise black outfits).

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.

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1. Prada Tall Leather Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Saks Fifth Avenue

This is the boot of my dreams. It is bananas expensive ($1,350), which I could probably create a compelling cost-per-wear case for anyway, but…I’m not sure it’s necessary (see below). That said, for you hardcore Prada fans, this is definitely a wear-forever boot.


2. Loeffler Randall Gia Safari Tall Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Loeffler Randall

THIS is the boot I’m the most excited about. It’s still very pricey ($695), but is half the cost of the Prada boot, and the quality of Loeffler Randall is superb. I’ve been really happy with a few pairs of heels I have from this brand, so high hopes on these boots.


3. Loeffler Randall Safari Gia Boot – Black

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Loeffler Randall

For those of you who still prefer a classic black boot, my favorite Loeffler Randall boots also come in black. I’ve gotta admit these are seriously gorgeous, and completely nail that British solider/’60s mama vibe.


4. Loeffler Randall Heidi Tall Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Loeffler Randall

When a rich tan is deepened into burgundy…exciting things happen, and I’m obsessed with these boots. The heel is too high for me, but gosh: these are outfit-making boots.


5. J.Crew Sadie Knee-High Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: J.Crew

J.Crew also makes some pretty good boots! I’ve found that J.Crew’s boots aren’t *quite* as luxe as the higher-end brands, but they’re also $348 (and currently $100 off). This particular pair is almost a dead-ringer for the Loeffler Randall boots above (or heck — super similar to even the Prada boots) and are also available in black or a lighter camel as well. A solid purchase.


6. Frye Billy Pull-On Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Frye

I’m breaking my own rules here: these clearly do NOT look like a boot worn by an old English soldier — but cowboy boots, if that’s your vibe, are also considered classics. I like this particular pair because the shade is gorgeous — a dark, warm, broken-in brown with rich caramel tones — and the boot itself is a pretty intriguing blend of cowboy and motorcycle. These boots have a similarly timeless feel, even if the vibe is very different. Would look AMAZING with dresses — whoa.


7. Frye Jackie Jackie Button Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Frye

These boots are similar to the pair above, but the vibe is a little more ladylike, a little less tough-girl. Another really solid option, based on your personal style.


8. Vince Camuto Phranzie Knee-High Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Nordstrom

I have a similar pair and LOVE them. But a few readers have mentioned that they’re struggling to style theirs: how do we wear this color? Personally, I tend to wear these boots with lighter pieces — a silky summer dress that’s getting over-powered by rich browns or with cool-toned pieces. If light blue dresses are your thing (apparently they’re mine??) then these boots are a pretty safe bet. I also love wearing mine with all-black as a way to freshen up the look. (The exact boots I have are Sam Edelman’s Olly Boots, currently on sale.)


9. Philip Lim Tess Square-Toe Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Saks Fifth Avenue

Um. These gorgeous boots are made from “corduroy suede” and sometimes when a boot is this freaking fabulous, we’re calling it a classic. Wow. I’d wear these with gloriously textured sweater dresses, too.


10. Silent D Kitten-Heeled Slouch Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Anthropologie

I think this photo is a little misleading…these boots are made to slouch a bit. That said, the boots are still based on a timeless silhouette (the slouch is just a fun twist), and come in a ton of colors.


11. Stuart Weitzman City Knee-High Tall Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Nordstrom

These are not knee-high boots, they are, in fact, over-the-knee boots, but I’d be remiss if I didn’t at least mention them. I have had these boots for years, and have paired them with many, many dresses, all winter long. Furthermore, if you are unapologetically team skinny jeans AND/OR live in a really cold climate, you’d be hard-pressed to find a more practical dress-up boot. They especially shine with mini dresses and tights, or to make my workout leggings look like real pants.

12. Jeffrey Campbell Colorblocked Boot

Tall boots & a dress is 1 easy answer when I want to look effortlessly put-together...but jeans aren't quite appropriate. Or when it's still a little too warm for jeans and a sweater.
picture credit: Anthropologie

Sometimes, if a boot is just fabulous, it’s a classic. And I still have a reallllllly old pair of patchwork boots that I bought during the bootcut-jeans-and-heels phase of the early aughts. I’ll never get rid of them…because I love them still. And frankly, it doesn’t hurt that the patchwork is done in similarly neutral tans/camel tones, either.


Good luck boot shopping, Gang!! I’ve had a few pairs sell out from under me (annoying) so we scrambled to try and get this one out there before it was too late.

xo,

S

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