Ok this doesn’t count as one of the outfits. Photo just for fun. Outfit details sans baby linked below 😂 Unfortunately cannot link baby as she’s custom made. 😜 June’s bear suit is no longer available but you can read my review on her Babybjorn here!
One of the most common questions I get these days is how to create interesting winter looks that are stylish but warm–specifically without exposed ankles! As we’re still in the depths of February, we still have a ways to go before we reach Spring weather here in Chicago. 😬 Now I’m getting extra creative with my existing wardrobe to mix things up. I’ve especially been wearing a lot of sneakers with socks lately and I feel like it’s been helping get out of my “boots and leggings” style rut! If you also need some warm (but stylish) outfit inspiration, here are 10 looks you can copy! The outfits rounded up below are from the past year–some old, some new–but I still wear these formulas over and over again!
Before we jump in, let’s go over some style tips that may help as you’re putting your outfits together:
First, some tips on styling socks with straight leg/cropped pants:
Color of the socks:
My biggest tip: you want to choose sock that goes with the color scheme of your outfit. Sometimes that will be in the same color as my pants (i.e. black socks with black pants), other times that will be the same color as my top (grey socks with a grey sweater) or the same sock color as my booties (i.e. tan socks with tan booties). You may have to experiment with these three options to see which one looks right–it will depend on the outfit! Most of the time though, I think it’s easiest to choose a sock that is the same color as your booties. When in doubt, start there!
Shop sock options here:
Thickness of the socks:
When your socks are showing, I recommend going with a wool sock that isn’t too thick–as socks that are too thick won’t look flattering and will give you cankles. 😜 I really like Smartwool socks–they’re very warm, but not bulky and they hold up really well! Amazon also has tons of neutral sock options with great reviews if you are wanting a little more bang for your buck! I wear the socks from this multipack ALL the time and I love the colors!
Length of your pants:
Pant length Tip #1:
When styling a bootie with straight or wide-leg jeans, my tip is to ensure the bottom of your pants hit right where the top of your boot hits, or even leaves a little tiny bit of room in between. You don’t want TOO much room, but a little bit is good! (This isn’t a hard and fast rule and can be broken, bit I find this look is easiest to style when this is the case).
Pant length Tip #2:
AND/OR ensure you are wearing straight leg jeans with a bootie that has a higher shaft and is slim around the ankle. This will ensure that it’s a flattering look and won’t make you look like you have odd cankles or tree trunk legs.
Color Scheme Tip:
Sometimes you can get the shape of the pant/bootie right, but the color scheme is off. Try playing around with the color of your bootie based on what you’re wearing. I find that a color scheme here is best. A camel sweater with jeans and tan boots, or a tan sweater with black pants and black booties (with black socks, if needed). You can use the same approach you would with tights–if there’s too much color-blocking, it may look funny. Try going with a more minimalistic color scheme if you can’t put your finger on why your outfit looks off. Don’t be afraid to mix and match–try a different wash of jean, a different shade of top, a different color of pant, a different colored shoe, etc!
Troubleshooting your outfit:
Some common reasons your outfit might not look quite right:
When the shoe and the pant leg are the same shape–that’s when it feels odd to me–a bootie with a wider shaft paired with a pant that is straight leg (i.e. the same width pant leg as bootie opening). Your pants may also be too long resulting in that funny “tree trunk” feel. (Try rolling them!) Your pants also may be too short to where too much sock is showing and it makes you feel costumey. OR, if the shaft of your bootie is cut too low and too much of your foot is showing–that can also look strange.
Try a boot that fits a little differently, or you find that you need a shoe with a bit of a heel, or a different shaped toe, or like referenced above, a different color! Try changing into a different pair of jeans. Not every pair of pants is going to work perfectly with every pair of shoes. I have some straight leg jeans that are shorter/longer than others for this reason.
Absolutely keep playing around–it may take a few tries to get it right, but you’ll soon get the hang of it!
10 warm winter looks without exposed ankles
Sweater (runs big, wearing small, but could’ve done XS), Levi’s 501 jeans (I’m 5’6 and have the cropped 28″ inseam but they come in 26″, 30″ and 31” I think they’re TTS, no stretch, but they will stretch out with wear.) socks, Everlane Court sneakers (reviewed here), NUULY rented graphic tee, ABLE Delilah Belt Bag (use code JESSKEYS15 for 15% off!)
I love this layered look–typically I would wear a cardigan buttoned down the front and then front tucked, but here I’ve worn it as a true “cardigan” second layer, and I love how it looks worn over a tee! This is a great way to add warmth, and if you’re dying to wear a spring outfit despite the cold, choose springy colors, and add some socks, and you’ll still achieve a similar effect!
This belt bag from ABLE is brand new and I am LOVING the slim profile and the ability to wear it as both a cross-body and belt-bag. If you’ve been looking for one that is slimmer and less bulky, this is a great one. It has a magnetic closure, slots for cards inside, plus a hidden zipper pocket in the back which is the perfect size for a passport! (It would be amazing for travel!) I love the cognac color that will only get more beautiful with wear, but it also comes in black leather!
Amazon coat (see review/sizing here), Levi’s 501 jeans (I’m 5’6 and have the cropped 28″ inseam but they come in 26″, 30″ and 31” I think they’re TTS, no stretch, but they will stretch out with wear.) Amazon sweater (reviewed here), similar socks
Similar to the above, I love a sweater in fun colors to brighten up your wardrobe when its still cold outside! This one from Amazon is lighter weight, so it’ll be cute to wear with shorts once it warms up, and it won’t break the bank! See it reviewed here! Worn with a lighter colored puffer, light jeans, and sneakers, it’s a great casual springy (but warm) option.
Similar cropped Madewell cardigan (also similar at Target here!),J.Crew Tissue Turtleneck tee TTS, but size down for a tighter “bodysuit-like” fit. Old Navy fleece-lined “warm” jeans, Caslon water-resistant Chelsea boots (TTS, I wear a thicker sock).
Another way to play around with layers–wear a tissue turtleneck as your base layer! It adds warmth, but. not bulk! I like the double layering here with the cardigan, but also could’ve thrown on a crewneck sweater, or unbuttoned the cardigan like I did in the first look above. I tucked it into my favorite fleece-lined jeans and wore black socks so not even the slightest sliver of ankle is showing!
These water-resistant Caslon Chelsea boots have been my #1 seller this winter for good reason. They came out with new colors as well, and I can’t recommend them enough–both during winter and as we transition into spring! I have trudged through MANY an icy puddle (and slippery sidewalks) and they’ve held up perfectly.
Similar camel turtleneck sweater, Similar cropped Madewell cardigan (also similar at Target here!) Levi’s 501 jeans (I’m 5’6 and have the cropped 28″ inseam but they come in 26″, 30″ and 31” I think they’re TTS, no stretch, but they will stretch out with wear.) LOFT clog booties (Roomy fit, I love them and ordered TTS, but wear thick socks!) Target also makes similar ones in cognac and black colors!) Similar beanie
This was the outfit I put on this morning (when it was 7 degrees with the wind chill!) I’m wearing my Uniqlo heattech thermal top and leggings underneath for extra warmth (a good alternative to the Old Navy warm jeans). I also ayered a turtleneck sweater and a cardigan over the top–another “extra warm” trick!
I like wearing these jeans on really cold days because they’re a tiny bit longer than my other straight leg jeans (I have the 28″ inseam) so there’s no exposed ankle, but they’re still cropped at a flattering spot. (Plus the leggings and socks provide two layers of protection for ankles, too!)
ABLE Elizabeth cardigan c/o, (doubles as a midi sweater dress too–Reviewed here! Use code JESSKEYS15 for 15% off your ABLE order!) Levi’s 501 jeans (I’m 5’6 and have the cropped 28″ inseam but they come in 26″, 30″ and 31” I think they’re TTS, no stretch, but they will stretch out with wear.) ABLE Eliza booties TTS c/o, ABLE Mae tee, socks
An outfit full of great wardrobe staples! You’ll recognize this look from my ABLE try on this past fall. (Note my code is updated since that last post–it’s now JESSKEYS15 for 15% off!) I love this sweater because it can be buttoned and turned into a midi sweater dress–it’s SO incredibly soft, meaning you’ll wear it at home but it’s also amazing for work as well. Makes an awesome layering essential! You can see I’ve also rolled my jeans here (same as you’ve seen above, but rolled for a different look, where you can see a tiny bit of ankle is exposed!)
Sezane sweater (sold out in white, but available in other colors! The Achille, which I also have and love, is similar and available in white! Sezane sweaters in general run roomy so size down if you don’t want an oversized fit), Madewell “Perfect Vintage” jeans in Fitzgerald wash (TTS! I also love this color for a slightly darker wash!), LOFT clog booties (Roomy fit, I love them and ordered TTS, but wear thick socks!) Target also makes similar ones in cognac and black colors!) socks
Here’s another example of choosing a sock that is the same color as the booties–notice how just a sliver of ankle is showing. You don’t want TOO much showing–otherwise it might look costumey–but also, since the shaft of the bootie is a little wider than the bottom of the jeans (they have a slightly slimmer leg than my Levi’s!) it looked odd without a little bit of space in between the top of the boot and bottom of the pant, so I rolled my jeans. This would be great for daytime or a casual date, too! I love Sezane sweaters because they’re so easy to dress up or down!
Amazon coat, ABLE sweater (it’s SO SOFT. TTS-use code JESSKEYS15 for 15% off), Everlane Cheeky jeans (ankle length, TTS), LOFT clog booties (Roomy fit, I love them and ordered TTS, but wear thick socks!) Target also makes similar ones in cognac and black colors!) socks, similar beanie
I wore this outfit out for a daytime date earlier this winter! Here’s another sock color example: My first choice would’ve been beige socks (like I wore above) but they were dirty, so I went with a lighter charcoal sock instead, and it was close enough to the color scheme of my outfit to look just fine! These jeans are a bit shorter than other pairs I own (they hit above the ankle) but this outfit still works because the shaft of my boot is high–above my ankle–so again, there’s only a tiny bit of space in between the bottom of the pant and top of the boot! I like that this outfit is all neutrals (camel and olive) but the pop of the red beanie makes it a little bit more fun!
Similar bodysuit that I’m wearing in the first photo here from Madewell and Amazon (also love this square neck version) If you don’t love bodysuits, you can get the same look with a tight-fitting turtleneck! (Like I’m wearing in the second photo). Old Navy fleece-lined “warm” jeans (run roomy), Blondo tall waterproof boots (TTS), Sezane belt, ABLE Moto jacket (out of stock but will be restocked soon!), old Everlane cocoon coat (sold out but you can find secondhand on several sites if you google!), Caslon water-resistant Chelsea boots (TTS, I wear a thicker sock), similar beanie similar socks.
Above you’ll find two different iterations of the same outfit styled differently for different occasions! The variation on the left you’ll find in my “Winter Date Night” outfit roundup. The photo on the left, while it’s the same combo on top and bottom, it’s more casual with socks, Chelsea boots, and a beanie, and would be great for daytime or a casual night out with friends.
Amazon tunic sweater (runs big, size down! I was pregnant here so didn’t size down and got a small–it worked great for a bump),fleece-lined faux leather leggings (couldn’t find my pair anymore but those are very similar with great reviews!), similar boots, similar beanie
This was one of the few outfit formulas I lived in last winter when I was pregnant, but one that I often wear now, too! Sometimes you just want a big ole oversized sweater, and this is my go-to! You could easily wear this commuting to the office, remove the beanie (I like a headband to disguise hat hair!) and then swap your shoes for flats or loafers for a more biz cas look. (I’d totally wear my Rothy’s cap-toe flats with this look!)