As the Dog Days of Summer behind us, I’m still left wanting to wear all my short Summer skirts and easy tops. To me dressing in the Summertime is far easier than in any other season because it requires (usually) so little clothing. Transition to Fall can be a challenge.

But with a couple of tride and true key pieces at the ready like my Everlane Denim Skirt, I feel way more confident about transitioning my wardrobe. I typically like to find one or two bottoms that fit perfectly and that I can wear over and over again without having to think too much about it. And Everlane’s Denim Skirt is one of them.

It has been a blockbuster hit. So much so they’ve sold out a number of times. That means that you might even own one of their coveted staple pieces and are looking for ways to style a basic denim skirt. Even if you don’t own their exact skirt this is still a helpful tutorial on how you can create ultra basic outfits to build upon as we straddle that special time of year when it’s hot cool and muggy in the morning and H as B (hot as balls) in the afternoon.

In this post, I’m going to show four incredibly easy ways to style Everlane’s denim skirt in “vintage light blue wash” using all Everlane items plus some vintage and second-hand shoes.

Styling basics for seasonal transitions

The key here is to keep it very simple. You don’t need a lot of accessories, jewelry, or outerwear to style cute and comfortable outfits for Fall. Although you can add all of these things if you like – these outfits are simple, stylish, and easy to throw on in a rush.

They work for any age, body shape, and size. If you want to cover more of your leg, choose a longer denim A-line skirt. But the basic concept of each outfit can work for anyone.

I’ve intentional kept them neutral so you can add fun items like scarves, necklaces, and outerwear to each outfit. You can think of each outfit as a base layer to build upon if you wanted to.

The only thing I’m changing in every outfit is my top and my shoes. It may be a subtle change, but it gives you options to work with.

Look 1

In the first outfit, I’m wearing The Pima Micro Rib Scoop-Neck in black in a size small. I ordered this on a whim and it has turned out to be one of my new favorite staple pieces. So much so I’m ordering a couple more so I can swap out and create a true capsule wardrobe.

This top is incredibly versatile, comfortable, and flattering. It’s a must in my opinion but keep in mind that is it a form-fitting shirt, so order true to size. It will show every curve.

The main attraction, of course, is The Denim Skirt in Vintage Light Blue Wash with Raw Hem. I ordered a size 27, which is what I normally wear in jeans depending on the brand (I can range from 27 – 29). But because of the nature of this type of denim skirt, you would probably need to order down a size. However, my main concern here is that it will be way too short.

But all in all, I love this piece and think we will continue to see Everlane produce more styles of denim skirt in stretch denim as well.

For my footwear in this outfit I’m wearing a pair of second-hand espadrilles I got at the thrift store. Here are some similar ones.

Look 2

Ok – so I know these outfits are nearly identical, but you could easily change the color of the top and get away from the uniform look. But if uniform-dressing is your jam, then this outfit with The Pima Micro Rib Open V-Neck would be great. I ordered it in black, size extra small by accident. So I’ll be exchanging that for a size small.

There is actually a small family of Pima Micro Rib items that Everlane is producing and I have to say I’m tempted to double down and get one of each as the budget permits. They are that comfortable, versatile and flattering. The quality is excellent as well. I accidentally threw my scoop neck in the dryer after washing, which I never do and it came out just fine without any shrinking.

This top is great for layering and you could easily build up some warmth with a leather, wool, or denim jacket on top. Or add a heavy scarf.

In this outfit, I’m wearing vintage Cole Haan red woven leather flats. Here are some similar flats you can get on Everlane that I think would complete this outfit rather well.

Look 3

In the third look, I’m wearing an older piece from Everlane, The Boxy Striped Tee in a size small.

Because it is heavier weight, you’ll much warmer and it makes for the perfect transition piece. Think of it as a super lightweight sweater; more of a sweatshirt. I believe they are currently sold out but you can order an alternative, The Heavyweight Tee.

I love this boxy style of tee with a few exceptions. A smaller bust can more easily pull off the “swing” effect of these kinds of tops. Typically, I tend to stick to more form-fitting tops because I like the way they look on me. From the side, swing tops or blouses can make you appear wider than you are, so that is something to consider when buying.

A staple item in my closet is my Lotta From Stockholm Moheda Swedish Clogs. I wear a size 37 and they have seen me through 3 or 4 Summers now. Handmade in Sweden and priced affordably under $100, these clogs are one of the best purchases I’ve made. They aren’t for hard-core all-day wear. But I can happily wear them around town while running errands. Plus they are bio-degradable because of being made entirely out of natural materials.

You could easily swap these open-toed clogs out for closed toed clogs or even boots to get more warmth for the transition to Fall.

Look 4

And finally, I’m wearing The Ribbed Wool Cashmere Cropped V-Neck in a size small.

Everlane is no longer stocking this item but a great alternative would be The Texture Cotton V-Neck. Same shape and cut.

You can see that I’ve started with the lightest weights and materials and moved to pieces with more coverage and warmth. This style of sweater is a must and I think ordering one in black and cream would give loads of styling options throughout Fall and Winter.

My Superga Tennis Shoes are one of my favorite buys of the year. Comfortable, well made and versatile, they are a go-to shoe that works with just about everything in my closet.

In conclusion

Transitioning your wardrobe from late Summer to early Fall is easy when you focus on creating base outfits to build upon. Use lighter layers on the bottom and build with thicker layering pieces on the top. Don’t be afraid to keep it simple and easy so you can change and get dressed quickly.

If you have Everlane’s denim skirt or a denim skirt of any kind, I’d love to know how you personally style it. Let me know in the comments below!