15 Outfit Ideas To Wear This Winter 2023 Featuring My Top 5 Most Worn Shoes
Nothing will snap you back to reality quite like arriving home to thirty-degree temperatures after trips to Hawaii and Mexico. I’ve had an incredible two weeks enjoying sunshine and shorts but it’s time for a reality check—we’re in the brunt of winter which means I’ve got rows of boots and sweaters calling my name.
Today I’m giving you fifteen outfit ideas to wear this winter—realistic, easy-to-recreate looks for the typical twenty-something. Whether you’re headed to the bars, a coffee shop, or into the city I’ve got you covered. I’m also using this post as an opportunity to highlight my five most-worn shoes of the season. Enjoy!
(click pink text for direct links to shop)
Brown Waterproof Bootie
If you’re looking for a waterproof boot that’s still stylish, these Dolce Vita’s will be your best friend. These are super similar in style to the Steve Madden Hutch boots that I always rave about- however, these ones can get wet which is a must during these slushy/snowy winter months. These come in several colors and are true to size. The perfect height to dress up a look but still short enough to walk miles at a time in comfort.
Blair Waldorf’s Calling
When I was in Europe, I beacame obsessed with the skirt + sweater vest combination. Nothing leaves you looking chicer! Sticking with winter whites and wearing a mini skirt + long sleeve to match. Then popping on one of my favorite sweater vests- this outfit also works with an oversized sweater to give that effortless “Pinterest vibe”.
These boots have just the right heel height to elongate the legs. Popping on matching socks to elevate my look and a few black accessories for a fun pop. Add tights accordingly.
top || skirt || sweater || socks || boots || headband || purse
The Never Fail
Whenever I’m in a rush or don’t feel like putting much thought into my outfit I’ll throw on a black tee, black jeans, and a cute scarf. I’ll then slip into a pair of boots that match the scarf and bam! Easy, cute outfit in just minutes. The options are endless with this one and it scores me compliments every time without fail.
top || jeans || boots || scarf
Bundled in Neutrals
You just can’t go wrong with a sweater and jeans this time of year. Works for every occasion and will leave you nice and warm! I have this oversized v-neck sweater in five colors and it’s the best. I size up to a medium and wear it with jeans, yoga pants, skirts, you name it.
This time around I’m reaching for a simple pair of straight-leg jeans and tossing on my most worn scarf- a light beige! It matches this adorable crossbody I bought while I was in Morocco, Africa so perfectly. Pop on a darker pair of boots to keep the eye interested.
sweater || jeans || boots || scarf || purse (handmade in Morocco, Africa)
Black Boots
You need a good black boot in the wintertime. If I’m being honest I tend to rotate between my Steve Madden Hutch and these slim Chelsea-style booties that have a narrower toe box—just depends on what I’m feeling that day. Both are great shoes but the Steve Madden are definitely more comfortable.
20 Something Chic
I just got this bodysuit and jeans combo in the mail from Abercrombie and while I love these pieces on their own, I think I love them more styled together. The basics collection from Abercrombie is amazing. The pieces are 100% cotton so they launder so well and yet are thick enough to wear without a bra + still sculpt out your figure. This square neck bodysuit is such a great staple piece- could work for the office, a dinner date, or even drinks with friends!
These jeans have an adorable seam along the front with a split hem along the bottom. I’m slipping into a taller, slimmer pair of black booties to complete the look. This is such a cute, sophisticated going-out look! Add a purse and you’re good to go.
Off To Class
When I was studying abroad I wore this outfit combo to class all the time. Start off in a fitted sweater and then layer on one of these thick shackets. They are super warm and boxy enough to layer up underneath. I have this in several colors so it’s constantly on repeat. Scarves and hats are a must if you’re walking to class- I learned that pretty quickly AND learned how convenient hats are for third-day hair haha.
top || jacket || scarf || hat || jeans || boots || purse
Free People Energy
Toss on straight-leg jeans and a pair of basic boots that match your top and you’re good to go! I can’t even tell you how many times I’ve reached for this combo over the years.
I got these culotte jeans from Mango while I was in Barcelona and they quickly became some of my most worn pants. They have such a boho feel to them. Because they are wider throughout the leg, they look great with so many different types of shoes, especially these slimmer booties. I’m keeping that Free People feeling with an oversized sweater and a huge scarf. Pop on a knee-length jacket and this outfit will serve you well during a day of sightseeing in the city!
sweater || jeans || boots || scarf || purse (handmade in Morocco, Africa)
High Top Converse
Platform high-top converse are arguably the most versatile shoe you’ll ever own. I have five pairs so I would know, lol. Not only are they some of the most comfortable shoes but also some of the most practical— easily transitioning from season to season and occasion to occasion. Whether you’re headed to the bars or class, they are sure to pull an outfit together. I’ve recently been obsessed with my “Move” sneakers- they have a lightweight, foam-like bottom that’s super airy. They weigh almost nothing so they are awesome sneakers to pack if you’re traveling.
Work From Home Fit
I don’t know if it’s just me but there’s something about this time of year that just makes me want to curl up in a pair of yoga pants! I wear my Aerie crossovers religiously during my work-from-home days. They are so flattering and come in bike shorts, leggings, and yoga pants- I have all three and rotate through them weekly. I typically just throw them on with a basic long sleeve.
If I’m headed out of the house a pair of high-top converse are the easiest to slip into. Just throw on a cute puffer vest and a beanie and you’re good to go. Bonus points if you have a Sherpa mini purse to match! This one is H&M and one of my most reached-for accessories this time of year.
top || pants || sneakers || purse || vest || hat
Quilted Cutie
While I do love my Converse with loungewear, they also pair perfectly with everyday clothes too! A sweater, scarf, and beanie are my go-to if I’m out sightseeing in the city. Converse keep my feet super comfortable for 10+ mile days and pair effortlessly with straight-leg jeans. This quilted jacket spices up this neutral outfit in no time. It’s got the cutest detail and is so soft—one of my favorite Altar’d State finds.
sweater || jacket || scarf || hat || jeans || sneakers
Boring Basics
I know this outfit is a hit boring but it’s truly one of my most reached-for looks this time of year. You just can’t go wrong with a crewneck sweatshirt and yoga pants for a work-from-home day. I always add Converse and a fanny pack if I’m running out the door for a few errands or to work at a local coffee shop! Such an easy look and gets me out of my pajamas haha.
sweatshirt || pants || sneakers || bag
Tan Sock Boots
Sock boots are what some people call an “acquired taste” but I’m here to tell you they really are a closet essential, especially if you’re looking to elevate your basic outfits. There’s something about this sleek, slimming shoe that effortlessly dresses up an outfit, making you look a little more mature. I wear these the most when going out to the bars with bodysuits and leather pants but I have also some basic “everyday” outfits for you.
Casual Dinner Date
Nothing slims the waist down quite like a cropped sweater with a pair of high-waisted jeans. I’ve been loving these split-hem pants from Abercrombie. It’s such a unique detail, however, they can be a bit tricky to style. Because the split comes up pretty high, I recommend a slim sock bootie to peek out.
Matchy Matchy
You’ve heard me talk about Express Body Contour pieces a million times now. These basics are a mix of polyester and spandex meaning they sculpt your figure and pair with everything. I have this high-neck tank in a gazillion colors, wearing them most often with chunky cardigans like this H&M one.
One of the reasons I love these boots so much is that they fit like a sock, so if you’ve got wide-leg pants sitting in your drawers, these are the perfect shoes to go with them! To contrast the bulkiness of the pants you get a slim tailored look with the boots on. I’m wearing those mango culotte jeans again (which I seriously need to get in another color).
cardigan || tank || jeans || boots || purse
Let’s Get Drinks
I’ve had a lot of people ask what to wear as a twenty-something when going out for dinner and drinks with friends! I almost always go for a pair of leather pants. These are definitely a step up from jeans but paired with a cropped sweater you don’t look too dressy! These pants are from Express and they are by far the best leather pants I’ve ever owned— I’ve tried all the cheap-y SheIn pairs and nothing compares.
The quality of these is unreal, hugging the waist beautifully. I do go up one size in them— I’m wearing a 0R here and am 5’2 for reference. Any time I wear leather pants I reach for sock boots. The slim-fit looks best and these have a baby heel that give you a little extra confidence boost.
White Low Top Sneakers
If you’ve been around my page for some time now then you know how much I love my Dolce Vita Zina Sneakers. While I do love my Converse, sometimes I just want a low-top sneaker. The Zinas are designed with tons of arch support- almost like an orthodic so they are insanely comfortable if you’ll be on your feet all day.
I wore these almost every day when I studied abroad, constantly doing 10+ mile days in them. I have three colors with the all-white definitely being my most worn! I personally wear these without socks and have never had any issues with blisters/rubbing.
Corporate Clean Girl
Even in a business casual setting, these sneakers work. I have so many corporate + teacher friends who have Zinas and rave about them. I’ve got them on with a basic long sleeve bodysuit, and culotte jeans. A knee-length coat and a cute purse will give this outfit that clean girl “city chic”. This is the perfect outfit for whatever your day might throw at you!
bodysuit || jacket || jeans || sneakers || purse
Travel Day Essentials
I also love my Zinas with yoga pants! I wear this outfit almost every time I travel on an airplane. You just can’t argue with the basis + these shoes don’t lace up like your typical sneakers so they are very practical for getting through airport security quickly! I always have a Lululemon fanny pack with me + I typically will throw over my chunkiest sweater or jacket to save space in my suitcase.
top || pants || sneakers || bag
Transition Attire
I tend to wear these shoes the most during the spring/fall because they really are a great “transition” shoe. However, they are so comfortable that even in the dead of winter I find myself reaching for them. I especially love the way these look with my ankle/cropped jeans. This pair always scores me tons of compliments. They are another Express find!
Up top, I’m keeping things casual with a lightweight ribbed sweater and a flannel layered over top. When I was in college this was one of my go-to outfits to wear to class. Super easy to throw on + with a puffer jacket you’re good to go for a walk to class.
top || flannel || jeans || sneakers || purse
What type of shoes are you wearing on repeat this winter?! I will say, I also love my Uggs for an easy throw-on-and-go shoe but ultimately find myself reaching for these five pairs most frequently. Let me know what occasions you need help getting dressed for. Working on business casual and going out blog posts as we speak. Stay tuned!
With love, McKenz
Latest Post: Oahu, Hawaii Travel Guide 2023 || Best Things To Do
Related Post: 16 Winter Date Outfit Ideas 2021
Instagram: styledbymckenz // YouTube: McKenzie Morgan // Pinterest: mckenzmorgan
