From straight to flare, here’s how to pair fall’s hottest cuts with the perfect shoe wear.
MADEWELL STRAIGHT LEG
This is hands down my favorite denim cut for fall. The relaxed shape and retro-inspired look feels fresh and comfortable for cooler weather.
Straight-leg denim comes in many different lengths though, which can make it tricky to style. When to roll up and when not to roll up is the task you’ll have to undertake when adding this jean to your wardrobe.
Here’s how to do it.
LOW TOP SNEAKERS
With this style of sneaker, you can leave the straight leg unrolled, because the top the sneaker and the bottom of the denim will likely only graze each other.
A little friction between the two is okay, while a lot can be distracting from your outfit.
If your straight-leg denim is long enough to cause more than a little rubbing between the two, simply add one roll to the denim, and you’ll be good to go.
WIDE-MOUTH SHORT BOOTS
The width of the wider-mouth boots and the width of the straight-leg bottom isn’t going to allow the denim to sit gracefully inside the boot.
You’ll need to move the denim out of the way of the boot by rolling it up once.
You’ll determine how large the roll of your denim should be by how much fabric you need to get out of the way of the boot.
If there’s a little denim sitting on top of the boot, roll once.
A bit more? Pull the single roll up more, so it’s wider.
A lot more? Do a double roll.
So much fabric you don’t know what to do with it?! Get it tailored to ankle length.
STACKED HEELS
If you’re excited to show off a more ornate shoe, you can use a roll to highlight the shoe.
Otherwise, pairing straight-leg denim with pointed-toe pumps or open-toe stacked heels (like these) will likely allow you to leave the denim unrolled.
KUT FULL-LENGTH FLARE DENIM
These pair of party pants are back.
While they’ll forever be an ode to the 70s, the 2020 update is clean, sophisticated and smooth.
I absolutely love full-length flares, but there’s one thing you need to know to dive into this trend: Full-length flares should always be worn with heels.
Here’s how to do it…
OPEN-TOE HEELS
Open-toe heels give you width in the front of your foot that some other heels don’t, which makes it a great way to add structure and balance to full-length flares.
You can also mimic the shape of the open-toe with a square-toe heel as well.
POINTED-TOE HEELS
Full-length flares are inherently long and wide, which means the shoes will take more of a backseat to these jeans than other denim cuts.
Use your statement pumps in this subtle way to further elongate your shape and add just a touch of power.
HEELED BOOTS
While heels go with full-length flares like PB goes with J, your highest heels aren’t always necessary.
These stacked heel boots are 2” or so and do just fine in elevating me enough to bring the flares off the floor and bring the energy upward through the rest of the outfit.
DL1961 RIPPED STRAIGHT
I’ve rid my closet of skinny jeans, so these DL1961 straights and my Madewell straights are my weekly go-to denim.
Straights are not all made equal, just like skinnies. As you’ve likely found out in the past, one brand’s fit can be vastly different from another, even if the description of the denim is similar. You might like sticking to one brand or many different brands when trying a new style like the straights.
Give yourself freedom to research and build your little closet collection based on what makes you feel good.
These DL1961 jeans are slightly different from the Madewell straights in the distressing, rise, stretch, and length. With a slightly different length comes different styling.
HIGH-TOP SNEAKERS
This combo is street wear at its finest, but getting it right means paying attention to both parties involved.
The height of the sneakers will determine how far up you’ll want to roll your denim. You can bring your denim to the tippy top of the sneaker to give it just a little friction between the two or clear the top of the shoe completely by rolling it above the top of the shoe.
In this look, I’m clearing the top of the shoe, but I do both. Choose the rolling technique based on your mood. What you feel like styling on any given day is what you should follow to find your perfect look.
CONSTRUCTION OR COMBAT BOOTS
These boots are thick and heavy. The mouth of the boot may be narrow though, which means fitting the rigid denim inside will likely result in bunching.
It’s time to roll.
Like the high-top sneakers, roll enough to clear the top of the boot or roll enough so the denim and shoe are barely touching.
NARROW MOUTH DRESS BOOTIE
These boots fit even tighter around my ankle than my construction boots, which means fitting the jeans in here is close to impossible.
While I could roll, the narrow top of the boot makes it easy for me to leave the jeans unrolled and relaxed.
The length of the jean allows me to still both highlight the boots and the natural silhouette of the denim.
NASTY GAL JOGGERS
If these aren’t comfy, I don’t know what is. COVID-19 has changed fashion forever, and in this current moment, it’s cleariest impact on the industry has been the rise in loungewear and athleisure.
I’m embracing it in my own closet in a number of ways. One of which are with those cozy, comfy joggers.
Here’s what to pair yours with…
LOW-TOP SNEAKERS
The ankles on joggers are often bound by elastic. This fitted detail makes them easy to pair with a low-top sneaker.
While these two elements sit close to one another, they tend to miss each other by a bit, so little styling is required.
You’ve even got some room in between, where you can add a colorful or patterned sock for an extra detail.
WIDE-MOUTH SHORT BOOTS
The tight ankle of the joggers makes these pants easy to slip inside short boots.
The second factor to consider though is fitting the boots with the overall shape of the pants.
A short boot that’s wide enough to create a “v” shape to feed into the width of the pant is a perfect pairing.
POINTED-TOE PUMPS
Add your pointed-toe pumps to your favorite joggers to bring these pants from day to night.
Like the low-top sneakers, both pieces will naturally stay out of each other’s way, creating a simple, but unexpected pairing.
Want more tips on how to pair fall’s hottest cuts with the perfect shoe wear?
