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Happy Friday, friends!

Two big things–first, I’m doing an Instagram Live takeover for the @StarbucksReserve account to give everyone a tour of their new Roastery opening on Michigan Avenue this morning! EEEK! Send me good vibes!

Second, I’m excited to be doing another styling session today with two IG friends who I think you will love following: Christin and Karla! I love teaming up with new influencer friends to style the same items several different ways, because it gives you guys so many more ideas!

We’ll all be publishing video styling sessions on our Instagram stories later today, so be sure to keep watch for those to go up later this afternoon! But until then, we’ll dive into this topic here on the blog!

Today’s styling session topic: Ankle boots with cropped pants!

When the three of us were discussing what to style, we all agreed that wearing ankle boots with cropped pants seems to be a pain point that EVERYONE has, so I hope you really love today’s tips and tricks!

To kick us off…let’s jump into some tips first!

Two rules of thumb for styling ankle boots: 

#1: You always want there to be a little bit of space in between your pant leg and your boot. Not TOO much, but just a sliver! This is the most foolproof rule to follow to ensure your outfit is always flattering! This typically means you’re going to need a boot that is cut a bit higher on the ankle–above the ankle, so it hits at the slimmest part of your ankle rather than right at the ankle bone. If your booties are TOO low cut, it will look funny!

#2: (I never really thought about putting this into words before, but I actually learned it from Karla in her “high ankle boot styling session”–when she explained it this way, it made SO much sense!) When you’re going for a cropped pants look, you want the boots to be slimmer than your pant leg. AKA, your pant leg should be wider than the shaft of your boot. This will still flatter the ankle! Otherwise it might make it look like you have odd tree trunk ankles. ?

You can wear socks!! So many people say to me, “but don’t your ankles get cold?” You can absolutely wear socks–just make sure they’re socks that go with the color scheme of your outfit. I find that typically a charcoal grey or black sock works best! If you’re looking for a great, warm pair, I highly recommend SmartWool socks!

Some of my favorite pairs of ankle boots: 

J.Crew Booties:

I just picked these up at J.Crew this past week, and they do not disappoint! Actually, I had planned to purchase this other leopard pair, but the shaft hit too high on my ankle and rubbed even just walking around in the store! I also think because they’re higher cut on the ankle, they’re actually harder to wear with cropped pants because then there isn’t space in between the pant and the bootie! BUT, thankfully I did find this pair–it has a pointier toe and a kitten heel, which make them really comfortable and more sleek due to the cut of the toe! They run TTS–I walked a lot in them the first day I wore them and no blisters, rubbing, or pain! They’re great!

Everlane Day Boots:

I own these in three colors and they are hands down the BEST ankle boots you can buy when it comes to comfort! They feel like literal butter on your feet because the leather is so soft, and the heel is just enough to make you look chic, but not so tall that you can’t walk for miles in them! My latest color obsession is the “ecru” color, but I also wear the “cognac” color a ton too!

Other Everane styles: I’ve got my eye on the Boss Boots as well. I actually thought they were too “edgy” for me in the past, but I actually really like how the snakeskin looks styled in an outfit––what do you think?! I also love the look of their Heel Boot which is like an elevated heeld Chelsea, if you’re wanting to go for something a little more casual/classic!

Steve Madden Jillian:

These are nearly sold out, but I wanted to list them because if you do wear one of the last few sizes, they are so worth snagging! They are the best neutral taupe, go with everything, have the perfect almond toe and are just so versatile. I’ve tried to find a similar version and can’t! ?

How to style ankle boots with cropped pants, 4 ways:

Outfit #1:

I love this casual look for everyday! Perfect for a weekend–day, or night! You can wear it out for a casual date night on Saturday night, or to your friend’s Sunday night football party the next day! 

Featured styled staples: 

Everlane Alpaca Sweater: 

Runs oversized, I’m wearing XS! This is probably my favorite sweater Everlane has made as of late, it is SO incredibly soft, and I love the brown/mustard hue–it’s so great for winter and looks flattering on a variety of skin tones! I also love the texture that it adds to every outfit!

J.Crew Jeans: 

I LOVE these jeans. If you want a lightweight, super-soft jean with a ton of stretch, this is your pair! I love the raw hem and the way they’re cut–I always say these (and the Everlane jeans I’m wearing below) are the best “starter” jeans for those who are wanting to branch out from skinny jeans–they’re super classic, versatile, but still feel attainable and not too “trendy.” Run TTS!

J.Crew Booties:

Run TTS–I walked a lot in them the first day I wore them and no blisters, rubbing, or pain! They’re great!

(Scarf is old) 

Outfit #2:

If you want to be casual and festive for holiday but don’t want to feel “over the top”––this combination is an awesome go-to! I think emerald and leopard print go together SO well–this is a perfect outfit to wear to a White Elephant party, Ornament exchange with girlfriends, or out to a cozy dinner! Need to dress it up? Just swap in a black skirt and tights! 

Featured styled staples: 

J.Crew Supersoft Turtleneck sweater:

I LOVE a good emerald green, but weirdly, I don’t own that much of it! (But I’m on a kick, because I just bought three things at J.Crew in emerald! ?)

Everlane Cheeky Straight jeans: 

Like I said above, this is the other pair of jeans I always point people toward when they’re trying to branch out from skinny jeans! They’re a super flattering cut, straight, cropped, but again, still classic and they don’t feel too “trendy.” I also love the color (the wash is the “Indigo” wash). They run true to size in my case, I wear size 25.

J.Crew Booties:

Run TTS–I walked a lot in them the first day I wore them and no blisters, rubbing, or pain! They’re great!

Outfit #3:

*I really need to clean my mirror…sorry! ?*

This is a great dressed-up look that you can wear anywhere. (This is also an example of a go-to outfit I’d pack for travel! You can wear it day or night!) It’ll be appropriate for a nice dinner on the town and won’t look out of place if you happen to go to drinks at the pub down the street afterward. 

Featured styled staples: 

Dudley Stephens Park Slope fleece turtleneck:

Warmer than ANY sweater you own–these are the real deal. I have worn mine more times than I can count over the past few weeks when the temps have dropped. Also, I love that they’re a small, women-owned brand that is made from recycled plastic bottles AND made in Brooklyn! I know they’re an investment ($158) but they are great quality and I have friends who say they’ve had theirs for years and they’re still going strong! They’re so versatile–wearable from the office to a date night, a football game–they’d also be great to wear skiing to keep you toasty on the slopes! See how else I styled this top here!  **Note: I just noticed that the black is out of stock now ?but I promise I’ll notify you guys when its back!** 

Everlane wide-leg crops:

Another Everlane staple I own in several colors–they are TRULY the best, most flattering pants! So easy to dress up or down.

J.Crew Booties:

Run TTS–I walked a lot in them the first day I wore them and no blisters, rubbing, or pain! They’re great!

 

Outfit #4: 

*I really need to clean my mirror…sorry! ?*

Same top, same shoes, totally new look! I wanted to demonstrate here how easy it is to adapt an outfit formula! With a simple swap of pants, this look becomes business casual–great for the office, but easy to transition from 9-5 to 5-9. You won’t feel weird or out of place grabbing drinks with your girlfriends after work! 

Featured styled staples: 

Dudley Stephens Park Slope fleece turtleneck:

Warmer than ANY sweater you own–these are the real deal. I have worn mine more times than I can count over the past few weeks when the temps have dropped. Also, I love that they’re a small, women-owned brand that is made from recycled plastic bottles AND made in Brooklyn! And I know they’re an investment ($158) but they are great quality and I have friends who say they’ve had theirs for years and they’re still going strong! They’re so versatile–wearable from the office to a date night, a football game–they’d also be great to wear skiing to keep you toasty on the slopes! See how else I styled this top here! **Note: I just noticed that the black is out of stock now ?but I promise I’ll notify you guys when it’s back!** 

Everlane Easy Pants:

I once had a reader DM me thanking me for turning onto these pants––she took a redeye to London and had to go straight from the plane into a presentation, and she said that even after the international flight, she looked polished and ready to go! They are wrinkle-resistant and super comfortable! They run TTS.

J.Crew Booties:

Run TTS–I walked a lot in them the first day I wore them and no blisters, rubbing, or pain! They’re great!

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I hope you loved today’s styling lesson! Head over to see how my friends Christin from @CBStyled and Karla from @KarlaReed styled their ankle boots with cropped pants!