How To Wear Boots Over 40

I get asked so many times about how to pair boots with outfits, and I think we tend to overcomplicate the subject. I know I do. But here’s the bottom line.

There are no rules. Not really.

There are a few best practices, and there are lots of preferences, but rules? Not exactly. If it works, it works.

But after trying 30 different combinations (5 boots with 6 outfits) I have some definite preferences, likes and dislikes, but most of these combinations work.

I do, however, have a few strategies that can help you feel more confident in your boot-and-outfit pairings. And I get into them all in today’s video.

Scale

If you’re going for a look that is more classic and flattering, as many of us are, then the scale of the boots should reflect the scale of your outfit. In other words:

• Sleek boots go best with sleek to medium scale outfits.
• Medium boots go with everything.
• And wide boots go with medium to wide outfits.

If you’re going for a look that is more trendy or edgy or funky, then you can contrast the scale of your boots to the scale of your outfit.

Clothing Styles

Dresses are the easiest to style with boots, particularly flowy dresses. They go with almost any boot style. Medium to wide leg pants are also relatively easy, as most boots fit nicely under their hems. Skinnies, as we all know, are the trickiest.

To Cuff or Not To Cuff

If the hem of the pants and the opening of the boot interfere with each other, you have three options:

• Cuff: This can be wide or narrow, a little undone looking or nice and neat.
• Turn Hem Under: With a skinny jean, tucking under shortens your jeans without creating a cuff.
• Tuck Into Boots: My least favorite, but this works if the jeans and boots are the same color (so black and black, lol). Otherwise, this can be updated by adding slouchy, fun socks to connect the boots to the jeans in an updated way.

And now, on to the boots.

I’m covering 5 categories of boots in today’s video. You should be able to find a category that correspond with your favorite boots.

Chunky Short Boots

These include chunky Chelsea boots, clog boots, rain boots, platform boots, combat boots, etc. You can find these affordable clog boots right here!

For a Classic Look, Pair With: Flowy dresses, straight-leg jeans, wide-leg jeans or flares

For a Funky Look, Pair With: Fitted dresses, skinny jeans, leggings

Sleek Short Boots

These include dress booties, classic ankle boots (especially those with a sleek pointed or squared off toe), most Chelsea boots, and sock boots. These boots from Free People are similar to my H&M boots, shown.

For a Classic Look, Pair With: Fitted dresses, skinny jeans, leggings

For a Funky Look, Pair With: Flowy dresses, straight-leg jeans, wide-leg jeans or flares

Lug Sole Boots

These are really in the chunky short boot category, but the lug sole gives them a different style that I felt warranted their own section. Any shorter boots with thick lug or thick rubber soles will fall into this category. These Sumissura boots are available right here.

For a Classic Look, Pair With: Flowy dresses, straight-leg jeans, wide-leg jeans or flares

For a Funky Look, Pair With: Fitted dresses, skinny jeans, leggings

Tall Wide Boots

This style can include slouchy boots, cowboy boots, rain boots, knee-high combat boots, some over-the-knee boots, and most riding boots. These Target boots are under $30 right now!

For a Classic Look, Pair With: Flowy dresses, straight-leg jeans, wide-leg jeans or flares

For a Funky Look, Pair With: Fitted dresses, skinny jeans, leggings

Slim High Boots

These include sock boots, some over-the-knee boots, fitted riding boots, stretchy leather boots, and fitted high-heeled knee-high boots. These Vivaia boots are on sale right now. And you can also use code NADA0511.

For a Classic Look, Pair With: Fitted dresses, skinny jeans, leggings (if they fit over these pants)

For a Funky Look, Pair With: Oversized outfits

These stretch boots are designed to be worn over the knee, but I experimented with wearing them below the knee for this video. They are very snug and did not work with the skinny jeans or the mom jeans (pictured). They worked easily with everything else, though.

Toe Shape Matters

Some hems can look sloppy with certain toe shapes. Flares and bell-bottoms, in particular, can look messy paired with certain shoe styles.

I really prefer the clean sleek look that the pointy and square-toe styles lend my flare jeans, over the round-toe clog boots.

I hope that you found seeing all of these combinations of boots + outfits helpful. What did you think of the pairings? And what’s your biggest challenge when it comes to wearing boots with your outfits?