Capsule Wardrobe Remix: How to Style Boyfriend Jeans Four Ways

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Can you believe it is our LAST post of our very October’s Capsule Wardrobe Remix!? Yes, I understand it is now NOVEMBER but the beginning of the week was October, you guys, so it still counts. 😂 As you probably know by now, I’ve been in San Francisco all week! (Sorry about the late posting times, by the way–for some reason my post scheduler is acting up and it isn’t posting them on time, and I don’t realize it until I wake up more than two hours behind everyone! This time change, man, it gets me!)

Anyway, I’m really excited to share four cute ways to wear boyfriend jeans with you today! Often, I think boyfriend jeans get a lot of “tomboy ” rap, but they can actually be really feminine and classic too! Keep on scrollin’–(scrollinnn on the riivverrrr. Why did it take me so long to think of this reference?!?! BTW that’s a GREAT karaoke song.)

First, let’s go over the capsule wardrobe items that I used to create these looks. Remember, these are all pulled from October’s Capsule Wardrobe Remix Item List that you can find here! (21 items total, and over the last four weeks, I’ve shown you how to style them 15 different ways in these posts! Also, stay tuned for next week when I’ll unveil NOVEMBER’s items! Yay!)

Capsule Wardrobe Remix: Boyfriend Jeans–Item List:

Boyfriend jeans: First thing’s first, why boyfriend jeans? 

I chose to include two pairs of jeans in this capsule: classic skinny jeans, and today’s hero–boyfriend jeans, because they offer two very different looks. If you’re looking to make your outfit look more chic and trendy, I think boyfriend jeans are an excellent way to do it. I recently got this pair from Everlane that I love. (Note: pay attention to sizing tips on their site! These are a little big on me. So size down if you want them to big a little more form-fitting/sit higher up on the waist.)

The fit of boyfriend jeans can really vary from one pair to another. I’d recommend looking for a pair that is still a bit fitted. You still want to be able to see your waist–nobody should ever look like they’re wearing paper bag jeans!

Other reader recommended boyfriend jeans: Topshop Lucas Jeans and the Topshop Mom Jeans (offer a similar look) Citizens of Humanity Liya Jeans (Splurge!) and Old Navy’s boyfriend jeans, AND some dark horses you guys–Abercrombie and American Eagle’s boyfriend jeans as well! (Who knew? I guess I need to check those oldies but goodies out again!)

Black pumps: I’ve owned this particular pair of Sam Edelman pumps for years. They’re slingbacks, and they’ve since been discontinued, but this pair is super similar in the d’Orsay style. This ankle strap version is adorable, too! I love Sam Edelman shoes (Nordstrom has a good selection and Shopbop’s selection is also diverse and totally different) They’re one of my go-to brands for footwear.

Heeled Booties: I chose one pair of booties that are light tan in color–the reason for this is because tan and/or light grey are probably the most versatile color you can choose in a pair of booties! Additionally, something with a low heel will allow you to wear them both day and night seamlessly. Not to mention, actually be able to walk in them!

These booties by 1.State go with everything I own, they are SO comfy, and are only $99! I love the shape of the toe. Plus, the fact that they’re cut out in the back too adds a little more visual interest! Because of the shape and color, they also help to elongate your leg, which is hard to find in a bootie, as most of the time they can cut you off at the ankles and make your legs look stubby! Another pair I own are these Dolce Vita Cassius booties, which are similar but more sleek, minimalistic, and classic. (This similar pair is also on sale for $98!)

Striped tee: I’ve said it before and I’ll say it again–when in doubt, choose a layer with stripes! I’ve found that classic black and white stripes add a lot more visual interest to your outfit than just a standard grey or white t-shirt. Plus, they look really cute mixed with other patterns, like leopard, or plaid! Again, mine featured here is old but this one is basically the exact same! I also love the striped “Perfect Tee” from J.Crew!

White button down: Often, the classic white button down gets forgotten about once you’ve moved past that “first office job post college” phase–and it’s a shame! White button downs are one of my favorite layers all year round. They look adorable with jean shorts and just as cute layered under sweaters, over leather leggings, or tucked into boyfriend jeans. If you’re looking to look polished and classy but still chic and on-trend, this is one of the easiest ways to do it!

Silk tank: You’ve seen me live in these this past summer–and I use the term “silk” loosely–honestly, any thin, flowy camisole will do the trick. Everlane makes some especially beautiful ones! I also love this burgundy one for only $29! I also just got this lace-trim camisole and it is to DIE for. So beautiful and really great for layering or all by itself.

Chunky cardigan: Another one you got a little glimpse of a few outfit posts back–this sweater by Free People–40% off right now! (I also love this similar one) is so soft and cozy it’s to-die for! Cardigans are essentials in the fall and winter. You can easily throw them on over whatever you’re wearing. This one is great to keep at your desk or pull on when you wake up on a cool October morning! (Or…January morning, let’s be real. Haha!)

Leather jacket: I now own two leather jackets–one brown and one black. The black one is my newest addition and I don’t know what took me so long to get one! I definitely love both colors and I think whichever color is best for you just depends on your preferences. The one I feature this month is sadly sold out but this one from Bernardo is similar and on sale! Bernardo makes a ton of really quality leather jackets that constantly get good reviews–you can shop all their jackets here. BlankNYC also makes super cute ones that are really affordable.

Leopard clutch: For the same reasons as I sing the praises of the leopard loafer, I love this leopard clutch. (Nordstrom actually has a TON of different leopard clutches right now!) I’m a huge fan of it for going out because it brightens up even the most basic outfit. Plus, it’s such a steal for less than $50 and it looks and feels like the designer version.

Leather tote: The Madewell Transport tote making the capsule wardrobe cut comes as a shock to absolutely none of you, I am sure. It’s my everything bag. Work, travel, groceries–whatever, this is always the bag I’m reaching for and it comes in several styles and colors as well.

Crossbody: I was so on the fence when I purchased this crossbody (it’s Rebecca Minkoff’s ‘Love’ bag in size small!) as to whether or not I would wear it, but I’d have to say it’ snow become one of my most reached for bags. I really love the fact that it’s olive, which is a neutral, but a really fun mix-up from the typical tan or grey. Although my exact version is no longer available, this one is nearly identical, just slightly larger!

How to Style Boyfriend Jeans: Look #1

Date night:

A slinky camisole has been my go-to for date night for many years. It’s sexy without being overly obvious, and I like the contrast of a beautiful, feminine top with a boyfriend jean. It’s upscale meets casual, feminine vs. tomboy. I often find that when you juxtapose two contrasting styles is when you end up with the most interesting outfit. Throw a leather jacket over your shoulders and cuff your jeans to show a bit of ankle in between your booties, and you’ve got a great date night look that is dressy-casual, without trying too hard!

How to Style Boyfriend Jeans: Look #2

Comfy morning at home

On those days where you want to get dressed because you don’t want to be a complete slob, but you want to be comfy while catching up on a book and having your coffee, boyfriend jeans, your comfiest tee, and a cozy cardigan are the essentials to reach for. You’ll also notice that I’m styling this three in the remaining two looks as well–because I think a striped tee is just as versatile as boyfriend jeans are! (Also, you can buy my cute mug that Cassandra made here!)

How to Style Boyfriend Jeans: Look #3

Drinks with the girls 

So, you know how I talked about mixing styles above? The same is true here. I love the look of a pretty, sleek pump mixed with tomboyish boyfriend jeans, the fancy, mixed with the casual. It’s unexpected, and I think that’s what makes this look work so well!

How to Style Boyfriend Jeans: Look #4

Casual Friday at the Office 

I’m really channeling my inner Jenna Lyons here. The great thing about a button-down is that it can serve as both an under layer (wear it under a crewneck with the collar sticking out, or a cardigan!) AND an OVER layer! I love it thrown on over a striped tee. Again, I think the word of the day for this post is “juxtaposition”. The more formal look of the white button down and pumps, paired with the casual elements of the tee and boyfriend jeans are just the trick to creating a really cool and polished outfit. This works so great for the office (whether your office has a more casual dress code, or if they don’t, hopefully they let you dress down on Fridays!) Also, to add more interest to your tote bag, it’s always fun to tie a silk scarf around it!

What’s your favorite way to style boyfriend jeans? 

P.S. If you missed any of our previous Capsule Wardrobe Remix posts for this month, make sure to check them out here!

Photos by Cassandra