Dangerfield Milkshake Skirt, Black Top, and How to Dress Confidently

Dangerfield Milkshake Skirt

I first saw this skirt on Sammi back in September last year, and adored it. What isn’t there to love about the sweet print, the gentle sweep of the skirt, and the delicious colors? I never got around to purchasing from Dangerfield, though, mainly because I completely forgot. Then about a month ago, she posted it in a buy-sell-trade group I’m part of on Facebook, right at the end of my clothing budget for the month. I was despondent, sure that someone would snatch it up before I could get to it.

Lo and behold, a few weeks later she bumped her post (which I had again forgotten about!) and I had a new clothing budget for the month, and it was mine! I don’t know how nobody grabbed it before me; it is the prettiest skirt, and will go with so many looks! I know that it’s technically a more spring and summer print, but I couldn’t resist wearing it right away, especially after discovering that Sara had bought the dress version!

The next time we see each other, we have vowed to do a twinning post, whether it be in these milkshake items or in our matching floral dresses. When you’re friends and fashion bloggers, it’s always imperative you collaborate on photos, obviously!

How to Wear a Dress Confidently

Speaking of dresses, I’ve been asked frequently how I wear what I wear with such confidence, so I finally made a video about it. If you’re not the video-watching type, don’t worry! I’ll summarize my points here for you. But if you are, you can pretty much skip the text in the rest of this post because you can watch everything I’m about to say right here:

Before I started fashion blogging, I basically hid myself in jeans and baggy tee shirts. I was not very confident, I had no style direction, and I didn’t think I could pull off the style that I wear today. But after a weeklong challenge to myself to wear skirts or dresses every day for a week in the middle of December, when it’s rainy and cold and mushy out, I realized… it wasn’t as scary as I had thought! And eight years later, here I am barely giving jeans a glance in favor of my usual dress or skirt outfit. So here are the five things over the years that have helped me gain confidence in changing my style:

One: Just Do It

The absolute most important thing is to just DO IT. Wear what you want to wear wherever you go, whenever you can, however you can. And you don’t have to start big: start with a simple skirt and a cute tee, if that feels more comfortable. You don’t have to go from jeans to pinup all in one day; it took me eight years! But I never would have become who I am today if I hadn’t just… done it. And I’m so glad that I got over all the insecurities and worries I had about changing my style, because I’m so much happier in a dress than I ever was in pants!

Two: Don’t Worry About Other Peoples’ Opinions

Sure, you can ask a friend for input, or get some help if you’re stuck on an outfit and how it goes together. But don’t worry what people are thinking about you. Where I live, wearing skirts all the time isn’t really done that much, and wearing vintage and retro styles is definitely a rarity. And when I first started really getting into the style I wear now, I was so afraid people would think I was trying to be better than them, or that I was being fake, or that I would just get unwanted attention.

But the more I wear what I love, the more people come to me and tell me they wish they had the guts to wear what I wear, or they wish they could pull off this look. And I always tell them: that’s what I thought, and then I just did it.

Three: Find What Makes You Feel Confident

Even in wearing dresses all the time, I have a comfort zone: that is, full, knee-length skirts and fitted tops. While I love to try other looks and silhouettes, my go-to thing day in and day out is a circle skirt and a comfortable stretchy shirt. Once you find the comfort zone within the new change, you will start to feel like it’s more doable. And you’ll start to feel more confident, and then less afraid to add another thing you want to try. I started out just wearing whatever skirts and tops I found. For a long time, I wore retro-cute, shorter skirts, things that were still semi-trendy. Then, I started wearing more vintage. Then, I started to do retro makeup and hair. Then, I added hats and headscarves. And now I’m basically wearing the exact vintage style that, eight years ago, I had no idea how to pull off.

It’s all about finding your confidence and comfort zone!

Four: Don’t Worry About Flattering

Don’t worry about what other people say is flattering on you, find what YOU think is flattering on you. Find something that you LOVE to wear, and wear it. Who cares if it emphasizes the “wrong” part of your body, there is no right or wrong in fashion. Wear what makes you happy, and what makes you feel like the best part of yourself. With my pear shape and my baby belly, all the magazines say I shouldn’t wear a pencil skirt. But you know what? I’ve done it and I loved it. It’s your body, and they’re your clothes. Wear what you love.

Five: Don’t Worry About the Size

And finally, don’t worry about what size is printed on your tag. Believe me, I know how hard this is. I have gained 50lbs in the last five years, I’ve been very pregnant twice. I used to wear a size 4 dress, and now I wear a size 12. I totally understand that it’s hard not to care. But here’s the thing: nobody can see that tag except you. Nobody will know if you’re wearing a size up except you. And if you’re wearing the size that fits perfectly and makes you look AMAZING… that’s what everyone sees. But if you’re wearing something that’s too small and the buttons gape or you can’t get it zipped or you can’t eat anything for fear of popping a seam, you’re not going to feel good about yourself. And that will show!

I am currently the heaviest I’ve ever been. And the most confident. I wear what fits, I wear what makes me feel awesome, and I work on being healthy even as I love who I am right now.

I hope you find something that encourages you to take a step towards wearing what you love!


Skirt, from Sammi via Dangerfield | Top, c/o Tobi (similar here)| shoes, thrifted | earrings and bracelet, vintage | headscarf, eBay (vintage)