How To Wear - October 19, 2017

How To Wear Any & All Kinds of Denim

what to wear with jeans

Jeans are the definition of an American classic and something I incorporate into my wardrobe on the daily. And if you look around, you’ll see I have quite the lineup of outfits with jeans. I could talk about what to wear with jeans in my sleep, basically.

Jeans are the one piece of clothing that can truly be dressed up or down, and go with just about everything. There are literally endless ways to style them, and other than business casual or events like weddings, you can wear them pretty much EVERYWHERE—all year round. Denim can also flatter every type of body style which is one of my favorite things about them.

With all that being said, it can be easy to fall into a rut with wearing the same type and styling the same way. It can also be a bit confusing knowing how to style each pair. I’ve taken it as my personal mission to be your denim guru and to layout ALL you need to know about wearing, styling, and straight owning your jean looks.

What to Wear With Jeans: Your Guide To Styling All Your Denim

Below I’ll provide an outline of everything you could ever think about when it comes to jeans (and probably more than you want to know). I’ve included outfit inspiration to show exactly what I’m talking about, plus there are links out to more specific blog posts tailoring to each jean type.

Depending on your situation, check the questions below to get answers to all your jean questions!

Where Are You Going And What’s The Vibe?

First up when prepping to style jeans, you have to know where you’re going and the look you’re going for. Since you can easily style jeans up or down depending on the occasion, I thought I’d make a few comments on how to style jeans for three different levels of dressy-ness (ha!).

Casual/laid-back (Brunch, Target, playground, the mall)

If you’re heading somewhere low key or just stepping out for a Saturday of errands, boyfriend, distressed, and skinny jeans are great options. You want something comfortable and don’t need to worry about showing off too much. I love wearing my jeans with sneakers or super comfy espadrilles or slides. Plus, I want something you can live in and not worry about getting dirty.


Concert, a happening bar, night out on town, art gallery

If you’re heading somewhere with a cool feel or want to be on trend, this is the time to play with your look and wear whatever jeans are trending. That might be flared, grey, black distressed, or cropped jeans.


Party, meeting your boyfriend’s parents, nice dinner

Jeans that are chic are ones that are flattering, classic, and most importantly, you feel good in. You can’t look chic without confidence, so this is the time to pick jeans that are in good shape AND look good on your shape. Flattering, dressed up jeans tend to be dark or black denim, something with slight stretch (but not too much!), or wide leg.

OK so now you know what look you’re going for. Now, let’s talk color.

Different Shades Of Denim: How To Style Colored Jeans

Things to consider: activity, weather, how you’re feeling

What to Wear With White Jeans

Perfection for spring and summer days, white jeans can actually be styled all year long – yep, even after labor day. The key for styling white jeans is finding a pair that is not sheer and that fit really well. White jeans shouldn’t be too tight – you definitely want some give. And in my experience, I think white jeans look best when cropped right above the ankle.

Related: What To Wear With White Jeans: Shoes, Colors, What Works & Why

What to Wear with Black jeans

I love black jeans with so much. It’s my go-to for days when I don’t feel my best or want to add edge to an outfit. Personally, I wear black jeans year round – yes, even in the summer. I wrote a whole blog post all about how to wear black jeans if you want to see more outfit examples and read about why it works!

What to Wear with Gray jeans

Great for days/nights when you want to go a little more trendy and add spice to an outfit. Gray jeans can serve as somewhat as a neutral and I love styling them with white, black, navy, and even light pink. They also look great with stripe combos of those colors.

what to wear with jeans, how to style denim, what to wear with jeans

Let’s Break it Down By Fit & Style

What to Wear with Boyfriend Jeans

These might not be the boyfriend’s favorite, but this style is perfect for when you don’t want to feel restricted. Boyfriend jeans are also perfect for when you’re wanting to sport a tighter top because they add great balance on the bottom. They can be kept casual with sandals or sneakers, but I personally love the juxtaposition of them paired with minimal, sexy heels like I did in this boyfriend jeans outfit.

What to Wear With Distressed Jeans

Another trendy pair, distressed are great for when you want to wear a classic or neutral top, but you don’t want your outfit to be boring. I love distressed jeans because they tend to be comfortable – the give/holes around the knee give really well.

What to Wear with Skinny Jeans

These have been the go-to over the last decade or two, and people have a love/hate with them. I personally love them because hello, you can show off your shoes! You can work with the fit (tight, more stretchy, baggy) depending on your preference and your top. I personally love skinny jeans when my top is a little more flowy/loose.

What to Wear With Flared Jeans

One of my favorite looks, borrowing this 70s style is a quick way to add a pop to an outfit. To modernize the flare, stay away from peasant, billowy tops when wearing them. I also love tucking shirts into flares because it cinches the waist! Flares should kiss the ground – any higher and they’ll be high-waters which is the opposite of chic. Further, they should start to flare slightly under your calf in my opinion. See more outfit ideas with flared denim here.