This week, our hero is one of the most underrated items in my closet. Why this dress is great: The sleeves are the perfect length and structured just the right amount to give your shoulders a great shape and long enough to provide coverage and slim your arms. The length is comfortable and the bottom isn’t so fitted that it rides up.

Another shocking bonus of this dress is that these horizontal stripes actually do NOT make you look wider. I’m not sure what black magic this dress possesses, but I have chosen to accept it despite the fact that I’m probably selling my soul in the process. Maybe it’s because the stripes aren’t the same width? We will go with that. This dress I bought at the secondhand store, but you know I’ve linked some similar ones below. 

A striped dress is a must because it is a “basic”, but can be dressed up or down and paired with such a wide variety of accessories. It is the easiest pattern to explore pattern mixing with. I went with animal print this week in the form of snakeskin, BUT a floral, leopard print or polka dots work great without feeling clashy, too. 

I almost never wear mini dresses or shorts because I am insecure about the keratosis pilaris on my legs. Never heard of it? It’s basically the worst. It is a skin condition that creates extra keratin around your hair follicles so you have little bumps all over the place. It’s also affectionately known as “chicken skin” (cute). A lot of people have this more prominently on the back of their arms. I have it around my knees and the back of my legs. If this sounds like you and you’re wondering how you can get rid of keratosis pilaris (or KP), I just invested in SkinFix during the last Sephora sale. I’m liking it a lot and have noticed a visible difference so I’m less shy about wearing a short dress these days. (not an ad, I really like it.)

That said, I was going through dresses recently and this one shone like a ray of light from the back of my closet. I think I heard the sound of a choir, too. It really is the best and adaptable for so many situations. 

Don’t have one of these in your closet yet, but feel like there’s a spot with its name on it? Here are FIVE under $40! (here, here, here, here and here)

Girls’ Lunch

I went with an all-black accessories palette for this look and kept it very simple. I started with these thick-strapped “wood” sandals. I got these at the same Payless going out of business sale that I got last week’s floral sandals. They are crazy comfortable. I am going to hope and pray chunky heels stay in style for another several years. I wore standard stilettos the other day and was wobbling all over. I am spoiled in these.

Because I wanted to dress it up a bit, I went with this black and gold statement necklace. I made sure it was close enough to the neckline so it didn’t feel too long or out of place. It’s definitely not my biggest necklace and the connectors are very dainty. I like the contrast of the bold stripes with something that feels softer. I debated between two other black necklaces and ended up with this one. Want to hear my thought process? Check out the video!

Lastly, I grabbed my tiniest Coach clutch. This was a bridesmaid gift from a wedding I was in. A great gift, too, because it is such a staple. I often will put all of my important things in it: licenses, cards, key, lipstick, etc. because I can just toss it into any of my other bags easily, or wear it by itself. I THINK my tiny, original iPhone SE even fits into it! Everyone rags on my small phone, but it fits into every single pocket and purse I own so I take the heat because I know I’m the real winner.

HEY! I also found a Coach-brand wristlet on their outlet site for $25 in the link below. S-S-S-SNAG IT!

I did toss a denim jacket over my shoulders since I’m always cold, but you could very easily go without it. 

Denim Jacket: 99% sure this is the exact jacket: here
Black Shoes: here, here and here
Wristlet: Similar COACH BRAND under $25 here, others here and here
Black Necklace: here 

The Spectator

You know, it’s weird blogging in a time when we really have very limited places to go and things to do. I totally see this look being perfect for a concert or sporting event. Good luck finding one of those to go to! Regardless, it is a casual and effortless look and will leave you prepared for anything.

I grabbed my favorite worn-in chambray shirt (chambray is a fancy word for denim, really) and tied it around my waist. I live for a way to cinch the waist. We all have one, some more dramatic than others, but tying something around it will always add definition because it will add volume to your lower half and therefore make it look smaller. Voila. I also like that the shirt adds coverage to my heiney, but also that I can put it on if I get chilly. We’ve already established that I probably will get cold so – a must. 

Also, please for the love of all things holy, when you tie something around your waist, make sure it is at your WAIST and not your hips. This will make you look wider than you’d like. Unless you have broader shoulders and are trying to balance it out, I would NOT recommend this. How do you find your waist? Bend over side wise and hold your finger in the spot where you naturally crease. That’s your waist! You. Are. Welcome.

No jewelry here because at this fictional event I’m dressed for there I’ll be active and don’t want to lose anything. I added a snakeskin crossbody that picks up the tones of the dress without being matchy matchy. It’s still anchored in black and white tones so it’s the ideal complement. If you’re looking to try pattern mixing, start with a pattern in the same color scheme as a safe first step. I wanted to keep my hands free so this is the perfect solution.

Lastly, I threw on these off-brand Converse inspired sneaks from Target. I have them in black, white and red and they are just as good. Don’t look too close. I was washing my shoelaces and never put them back in. So essentially, a real “threw this together” moment completely evidenced. 

Sneakers: Exact Pair here
Snakeprint Bag: here and here
Chambray Shirt: here and here

Patio Dining

This outfit was inspired by the band, Cake. Can you guess why? They have a song called “short skirt and a long jacket”. Even thought this isn’t a truly “long” jacket nor is it a skirt, it is still longer than the dress itself, so we will give it a pass. 

This chunky sweater is a lifesaver. I will wear it around the house over my pajamas in the winter or I will grab it an keep it in the car in case I need something. The color is neutral enough to be all-season and even though it is a thick knit, it is still structured enough to not swallow my frame. 

If you are uncomfortable in a short dress or skirt, this is a great way to be able to wear things you may have purchased in the past, but haven’t had the guts to pull them out in a while. It adds more coverage and length and still shows off your dress. If you are googling this to shop, you can search things like “long kimono”, “duster” or “long sweater”. A sheer version would also look great on this! 

I added lace up shoes with a modest heel. I thought about my black lace up shoes, but the nude helps my legs look longer, and in this dress I needed all the help I could get. I paired this with a secondhand Michael Kors purse that I could put more warm things inside. If I ever upgrade my phone to something larger, I will probably have to wear this bag more, too. 

Sweater: here, here and here
Lace Up Shoes: here and here
Tan Tote: here and here

Are you obsessed yet?

I mentioned a couple higher-level brand name items in today’s post, which won’t be the norm. I’m working on a post for how to get items like this in your budget. And as always, you can always shop the links for similar styles at lower price points. 

Whether your striped dress fits exactly like mine, or has a different silhouette, all of these variations would work for you. A wearable dress that never goes out of style is definitely something worth finding hanger space for. 

Too long to read? Check out our video talking you through these outfits below. And, not to really persuade you, but I find a REALLY fun surprise in one of my purses in the video that is suuuuuper exciting and I know you’ve all been there.

I shied away from the “midi” length for a while. I thought it was super awkward and extremely hard to find shoes that actually worked. As time went on, I warmed up to the midi. What’s not to love? It doesn’t ride up as easily as above the knee styles, less risk if the wind blows, always looks sleek and you only have to shave below the knee. Three times a win!

I was doing a Boohoo.com haul – looking for some affordable dresses for a “non-wedding day photo shoot” (#covidbride), and I saw this pleated, flowy number that I had to try. Plus, it was $16, so basically it bought itself. This one is sold out now, but here are some similar ones – all under $50. FYI – we will get into steals and deals later on.

It arrived and I LOVED it. It was a little longer than I expected, but there was still plenty that could be done with it. I immediately knew it would be a summer (and fall and spring and winter) staple. The length and shape can go from day to night, casual to office, trendy to timeless. I’m already picturing the re-do of this post when we get back to sweater and boot season – OMG YAY – so cute in my head! 

For now, I’ve determined three of my fav ways of how to style this black pleated maxi: out and about, soiree chic and to the office. Most of what I’m wearing has been in my closet for years, so I’ve linked to similar items – all under $25 each.

Black Midi Skirt Options: here, here and here

Out and About

Probably my favorite of all three looks, just because I can see myself wearing it the most. I tied up a graphic tee that my friend Maria bought me at a concert of my favorite band Dashboard Confessional (I had a very long emo phase). Mine is a ladies’ cut, so it is a slim fit. However, I think if you didn’t have a ladies’-specific tee, the boxiness would still look super cute with this since the fullness of the skirt would balance the top out. Don’t want to tie it up? Just tuck it in! 

I paired this with my trusty slip-on black sneakers (They are slim and low-profile so they don’t creep up and cut of the line of my short little legs too much and perfect for when I am running out the door) and a multi-colored clutch to tie in the color from the graphic tee and even more pop to keep it bright and casual. 

I was undecided on the necklace and could still go either way. If you want a more sporty spice look, get rid of it. If you like making it more feminine, keep it!

Graphic Tee: here,here,here
Slip-on shoes: here and here 
Multi-color clutch: here and here
Accent necklace: here and here

Social Soiree

I was originally going to call this look “Garden Party”, but I don’t know a single person who has actually been to one of those. So here we are…”social soiree”. I love a monochromatic look. It feel like it elevates separates to be a true cohesive outfit. Black on black? Even better. I got this bodysuit for $6.99 (WHAT?!) during the same Boohoo.com haul when I got the skirt. It’s sold out now, but I’ve linked some other options below. Any type of black bodysuit and fitted top would do here. 

I also love how tall a monochromatic look can make you appear because you’re not breaking up the line of sight from your shoulders to the bottom of the skirt. It’s a great tip for those of us on the petite side or dangerously close. However, we still want to accessorize in a way that gets us noticed, don’t we? I went with a hot pink clutch that is just big enough to hold my phone, cards, key and lipstick and called it a day. This guy has a strap so you can use it as a wristlet to keep your hands free. I got it secondhand, but I think it was originally from Target. 

Let’s talk about this shoe.  The watercolor floral is so soft and versatile. Realistically, I could have accessorized with: yellow, green, blue or white instead of the pink I chose to highlight. That’s the beauty of multi-colored accessories. They provide so much more versatility than a solid and are fun as heck. I got these at a Payless Shoes Going Out of Business Sale, but floral shoes are always going to be in style. I’ve linked a few below. I think the key on finding the right pattern is one that isn’t overly “crisp”, otherwise you run the risk of tablecloth territory. 

Bodysuit: here, here and here
Shoes: here, here, here and here
Clutch: here, here and here

To The Office

As companies continue to adopt less rigid wardrobe guidelines, it has allowed women to take risks in silhouettes that can look feminine, but also fully in-charge. Since this midi skirt is so flowy and unstructured, I wanted to use a traditional top half to keep it professional. 

I love a bright blazer. When I was in “Corporate America” I had one in nearly every color. The structure showed polish and organization, the color expressed personality. I paired this red one (from H&M back in the day) with a black and white silk, patterned blouse. I tucked my top into my undies so that it stayed as streamlined as possible. You don’t want it to balloon out of your waistband. A blazer can already add bulk to you, so this is an important step. You could use a bodysuit or a fitted top here just the same in order to fix this problem. 

I liked that the pattern was angular, again, which feels more professional than something floral or swirly. Lots of unspoken messages in this outfit. Once closing time hits, you can shed the blazer and head to whatever is the next item on your agenda! 

I thought it was important that I paired this “inspo” outfit with a bag I would have actually used on a busy work day. This one in particular has great details – suede end panels and fringe that would definitely draw some attention. It was a free Victoria’s Secret giveaway if you purchased a mountain of pink-colored items back in the day. I just flip the logo toward the inside to keep it “profesh”. If you work in a more traditional office setting, maybe a tote with more structure and less flair would suit you better.

I am not linking to plain black pumps, because there is nothing special about these and likely every woman already has a pair in her closet. If not, invest in a pair. I like to have a round toe and a pointy toe in my closet at all times. You can almost never go wrong with a black pump. This is my PSA. Thank you. 

Blazer: here and here
Top: here and here
Tote: here and here

So there you have it. I hope it didn’t take you nearly as much convincing as it took me to finally click “add to cart” on a Black Midi Skirt. It’s a staple that will allow you to reuse time and time again, and likely look different on each occasion.

Don’t want to read this article? Check out the video version on my YouTube channel instead!