Lookbook

I used to get the worst seasonal depression during the cold winter months. I was miserable and felt unmotivated and sad until Spring. But over the past few years, I have completely reframed how I think about winter and the things I do during these months. And as a result, winter has now become my (second) favorite season of the entire year. I really leaned into slowing down and immersing myself in things that make me happy. November and December are the months of giving but I call January the “month of me”. I don’t focus on resolutions or a “fresh start” but rather allow myself to slow down and indulge in anything that brings me joy. I thought I would share the things I do that have really helped me enjoy this season in case you  may need some inspiration for yourself.

Things I Do To Get Through (and Enjoy) Winter

Lie in My Sauna Blanket

I use my Higher Dose Infrared Sauna Blanket (discount code: MAREE15) all year long but it is a necessity in the dead of winter. It does so many amazing things for the body (read my full review here) and I love getting in it multiple times a week when it’s freezing outside. It gives me time to slow down and lie still which is something I don’t do very often but is so important during the winter.

Burn My Favorite Candles

I am a candle lover and burn them all year long. But especially in the winter, I stock up on my absolute favorite scent of all time and burn it nonstop. The scent is so comforting to me and instantly helps elevate my mood.

Drink All the Hot Beverages

I am a beverage gal and love to drink a variety of options throughout the day. I don’t drink any alcohol (and haven’t for nearly 10 years) but am constantly trying new drinks of all kinds. In the winter, I live for warm beverages throughout the day. I’ve been especially into this menopause tea (discount code: MAREE20) to help with my constant perimenopause symptoms as well as these bone broth packets for a bit of added protein (12g – 15g per packet!!). The bone broth packets are perfect to bring on the go and I sip on it while I’m out and about.

Live in Cozy Clothing

I am a matching pajama set aficionado at this point and have been collecting sets for nearly 10 years. I love getting dressed for bed and putting on a fresh new matching set on a cold winter night. In addition to that, I have tons of robes, fuzzy socks, slippers and cozy lounge sets that I wear around the house. I’m a homebody anyways but especially in the winter so I like to make my time at home as enjoyable as possible. And this includes indulging in clothing and accessories that make me feel cozy but also help to elevate my mood. I am someone who loves to dress up and feels better when I’m fully dressed. This also applies to what I wear at home so I really lean into wearing all the matching lounge sets and pajamas during this time of year.

Engage in Mind Numbing Hobbies

I have an anxious mind and struggle turning it off some days. To help with this, I love to do hobbies that allow me to turn my brain completely off in order to focus on the task at hand. My favorite mind numbing activity is doing puzzles. I have a favorite puzzle brand/puzzle artist and own so many of her puzzles that I rotate between. I also purchased a puzzle board that I can move around the house so I can do my puzzles anywhere.

Listen to Audiobooks

Reading books is something I have enjoyed since I was a kid though I don’t truly have the time or attention span to get through one these days. Because of this, I have been listening to audiobooks for the past 8 years and it’s been life changing! I now get through 6-8 books a month and love being able to get lost in the telling of a story.

Add a Bit of Self Tanner

When I’m really feeling the winter uglies, I will pull out my favorite in shower moisturizer that is also a self tanner. It’s incredibly easy to use and gives me just a touch of color to make me feel less ghoulish. LOL

Tons of Extensive Skincare Routines

I already love a long and involved skincare routine but in the winter I really go all out. I will pamper myself from the top of my head to the bottom of my feet. Ha! I indulge in a daily skincare routine, regular body care treatments, hair masks, longer oral care routines – you name it, I’m doing it all.

It’s officially boot season and I could not be more excited! I have more pairs of boots in my closet than I care to admit so I wear them all season long to get my money’s worth. LOL Especially when it gets cold, wearing flats with my jeans won’t cut it. I have a mix of boot styles in my closet – both knee high boots and ankle boots but tend to reach for ankle boots more when I’m wearing jeans. A simple classic pair of ankle boots with go with just about any pair of  jeans. For me a pointy toe, high heel ankle boot in either black or brown is a staple for me and something I wear year after year. It never goes out of style. In today’s post, I’m sharing how to style ankle boots with various different denim and hopefully give you some outfit ideas to recreate.

How to Wear Ankle Boots with Jeans

How to Wear Ankle Boots with Wide Leg Jeans

Wide Leg Jeans with a Striped Turtleneck

Sweater (code: MAREE10) | Jeans | Boots | Bag (similar) | Sunglasses | Necklace (code: MAREE20)

Wide Leg Jeans with a Tweed Jacket

Jacket (similar) | Turtleneck | Jeans | Boots (similar) | Bag | Sunglasses

When wearing wide leg jeans with ankle boots, it’s best to choose an ankle bootie with some height. This allows the wide leg jean to drape and skim the floor without bunching up or dragging on the ground. Either a pointy heel or a block heel would work – it just depends on your preference. This is one of the only style of jeans that may work with knee high boots if you want because there is more room for them to fit under the jeans. For more ideas of how to style wide leg jeans, here is a post with a ton of different suggestions.

How to Wear Ankle Boots with Straight Leg Jeans

Straight Leg Jeans and a Chunky Turtleneck

Sweater | Jeans | Boots | Bag | Sunglasses

Straight leg jeans with a barn jacket

Jacket | Sweater (code: MAREE10) | Jeans (similar) | Boots | Bag (code: MAREESYE) | Belt (similar) | Sunglasses 

Straight leg jeans are a great alternative to a skinny jean style because they are a slight step up in terms of looseness. Be sure when wearing ankle boots with straight leg jeans that they go under the jean and there is no bit of leg or gap showing. This will create a longer line and balance out the look. If you are wearing black jeans, try a black pair of ankle boots which will really help to elongate the look and create a seamless line from the waist to the floor.

How to Wear Ankle Boots with Cropped Jeans

Cropped Jeans and a V-Neck Pullover

Sweater | Jeans | Boots (similar) | Bag (similar) | Sunglasses

Similar idea with cropped jeans (or jeans that are ankle length) as straight leg jeans, be sure the top of the jeans still cover or meet the top of the boot. Also choose a slim style ankle boot or even a sock bootie so it balances out the proportion of the cropped jean. If you want a boot without any height, you can always opt for flat chelsea boots which would work too.

How to Wear Ankle Boots with Faux Leather Jeans

Faux leather jeans and a bodysuit

Turtleneck | Jeans (similar) | Boots (similar) | Bag (similar) | Sunglasses

Monochromatic look with faux leather jeans

Sweater (similar) | Jeans (similar) | Boots (similar) | Scarf (similar) | Bag (similar) | Sunglasses

I love wearing faux leather jeans in the fall and winter and my favorite way to style them is with simple black ankle boots. Either suede or leather is fine because both will look great with faux leather. I have them styled with a high heels ankle boot, but a simple flat classic ankle boot would work well.

How to Wear Ankle Boots with Skinny Jeans

Skinny jeans and a fair isle sweater

Sweater (similar) | Jeans | Boots (similar) | Bag (similar) | Sunglasses

I still have a few pairs of skinny jeans in my closet but I definitely style them differently now with ankle boots than I used to. I prefer the ankle boot to go under the jeans instead of over them. It looks more modern and doesn’t cut off my leg in a weird way. If you want to wear skinny jeans, choose a sock bootie or something very slim around the ankle to easily fit under and not look too bulky. Also make sure the hem of your jeans cover the top of your boot and doesn’t leave a gap.

How to Wear Ankle Boots with Distressed Jeans

Distressed jeans with a quilted jacket and lug sole boots

Jacket (similar) | Turtleneck | Jeans | Boots | Sunglasses

Distressed jeans and a wool car coat

Coat (similar) | Turtleneck (similar) | Jeans | Boots | Bag (similar) | Sunglasses

I showed two different ways to style distressed jeans with ankle boots. You can definitely dress them up a bit with a sleek pointy toe ankle bootie or choose something more casual like a lug sole boot. As with most of the other denim styles, I recommend having the jeans fall over the top of the boot instead of tucking them in. It looks more modern and elongating.

Though most of the denim I shared in this post are blue, black or dark denim, I still love wearing white jeans in the fall and winter. All my styling tips would apply to those too. If you need ideas of what to wear with white jeans, I have an entire blog post dedicated to it!

What Are Ankle Boots?

Ankle boots are typically defined as any boots that end near the ankle bone. That could be an inch or two above or even slightly below the actual ankle.

Types of Ankle Boots

Chelsea Boots

Chelsea boots are usually a flat boot that you can pull on easily. Typically they have elastic or a pull tab at the back to make them easier to get on without the need for zippers.

Pointy Toe Boots

As the name suggests, pointy toe ankle boots refer to the pointy shape of the toe. I find these to be the most elevated and timeless style of boots to own.

Lug Sole Boots

A lug sole boot is one with a thicker sole that is better equipped to walk in foul weather conditions.

Sock Boots

Sock boots are a fitted style of ankle boots that hug the foot and ankle tightly.

Kitten Heel Boots

Kitten heel ankle boots usually have a heel lower than 2 inches so it makes them much easier to stand in or walk for long period of time.

What Are the Most Comfortable Boots for Women?

The most comfortable boots are the ones that feel the best to you. Every person is different so it is a bit of trial and error determining what boots are the easiest to wear for long periods of time. If you do like a heeled boot, opt for a kitten heel style which still gives a bit of lift without being too high. I love chelsea boots for day to day life especially since there are dressier options available.

How Should Ankle Boots Fit?

It’s best to always get your ankle boots a tad big so you can wear socks or tights with them in the fall/winter.