I have this thing where I buy a dress for one specific event and then it hangs in my closet for three years because I never figure out what to do with it after. Sound familiar?
My sister Jenna teases me about it constantly. She has maybe eight dresses total and wears each one to death. I have forty and cry every morning that I have nothing to wear.
So this post is really for me as much as it is for you. I sat down one slow Sunday and worked through every dress-shape and color I own, plus a few I’m definitely going to buy, and figured out the shoes and bags and little extras that make each one work.
20 Dress Looks I Keep Coming Back To
Gold Slip Dress With Strappy Heels
A gold dress outfit sounds intimidating until you see it done simply. A liquid-y slip in a soft gold, thin straps, and that’s basically the entire event handled. You do not need much else.
Strappy heels in a matching metallic keep the leg looking long, and I like keeping the jewelry tiny here because the dress is already doing so much.
Sheer Maxi Dress Over Bodysuit
Here is the thing about a sheer maxi: it looks complicated but it is truly the laziest thing I own. A see-through floor-length dress, a solid bodysuit underneath, done.
This sheer dress outfit is the one I reach for when I want to look like I tried but I did NOT try. Flat sandals in the summer, a heeled boot when it cools down. The layering does all the work for you.
Silver Sequin Dress With Slingbacks
Sequins during the day feel wrong to most people but I disagree, respectfully. A silver sequin dress with a pretty slingback flat, worn to a lunch, is a small joy.
Of course, come nighttime it’s a different beast entirely and you can lean into it fully. But I love the idea of wearing something sparkly to an ordinary Tuesday just because you feel like it.
Light Blue Satin Dress With Pearls
This one is soft and a little bit sweet, which is not usually my vibe, but I keep coming back to it. A satin dress in a pale blue with a string of pearls at the neck is so classic it almost hurts.
The pearls make it. I know they can read old-fashioned but paired with the cool blue satin they feel fresh again. Kitten heels or a simple sandal, and you’re set for a shower, a lunch, a christening, whatever the calendar throws at you.
Dark Denim Dress With Red Heels
Denim as a dress is one of my favorite categories because it is so forgiving. A dark wash reads dressier than a light one, and a pop of red on the foot turns the entire thing chic.
I put together this denim dress outfit black women look for my friend Dana, who wanted something for a gallery opening but did not want to feel stiff. She wore a fitted dark denim dress with red heels and a small gold hoop and she looked incredible all night. And comfortable, which matters more than people admit.
Floral Babydoll Dress With Ballet Flats
A babydoll cut with a little floral print and a pair of ballet flats is peak spring-picnic energy. Soft, easy, a bit romantic.
I like this on those days where you want to look put together but you also might sit in the grass at some point. The flats make it walkable, the floral keeps it cheerful, and you can add a cardigan when the evening cools down.
Gold Fringe Dress With Minimal Sandals
Fringe moves, and gold fringe moves AND catches the light, so this is a lot of dress. Which is exactly why the shoe has to disappear.
A minimal, barely-there sandal in a neutral tone lets the dress be the entire story.
Sheer Lace Dress Over Slip
Lace over a slip is the trick that makes a sheer dress feel intentional rather than accidental. The slip gives you coverage and the lace gives you the pretty.
I love this in a deep color, forest green or a rich burgundy, over a matching or contrasting slip. It photographs beautifully and it feels a little bit old-Hollywood without trying too hard.
Silver Column Dress With Metallic Mules
A column dress is the most flattering shape for basically everyone and I will die on that hill. Long, lean, one clean line from shoulder to floor. In silver it becomes something special.
This silver dress outfit works for the fancy events, the ones with a dress code on the invitation. Pair it with metallic mules so your foot matches the moment, add long earrings, and stand up straight.
Sky Blue Strapless Dress With Clutch
Strapless can feel like a lot of skin so I like a structured bodice that actually stays put, in a happy sky blue. A little clutch tucked under the arm finishes it.
This is such a summer-evening dress. Rooftop dinner, an outdoor party, that kind of night. The color reads fresh against a tan and the strapless neckline is nice for showing off a delicate necklace.
Denim Corset Dress With Knee Boots
A denim corset dress is having a moment and I understand why. The structured top gives you shape, the denim keeps it casual enough to feel wearable, and knee boots turn it into a full outfit.
I would wear this to a concert, or to run around a city on a cool day. The boots make it feel tough in the best way. Add a leather jacket over the top and you are basically unstoppable.
Floral Maxi Dress With Woven Bag
The floral maxi is the workhorse of every summer wardrobe and mine is no exception. Long, flowy, printed with something cheerful, and paired with a woven bag it reads instantly vacation.
This is what I pack when I am going somewhere warm and do not want to think. Flat sandals, the woven bag, sunglasses, and you’re ready for the beach town, the market, the long slow dinner. It just works, over and over.
Gold Draped Dress With Cuff Bracelet
Draping is flattering and forgiving and when it’s done in gold it looks like something a statue would wear. In a good way. A soft draped gold dress with a chunky cuff bracelet is my idea of grown-up glamour.
The cuff is important. One big, sculptural piece of jewelry does more than a pile of little things ever could. Keep the rest simple and let that bracelet be the exclamation point.
Sheer Black Dress With Tailored Blazer
Sheer and black together can go a lot of directions, but throw a sharp tailored blazer over the top and suddenly it’s chic and slightly severe and I love it. The blazer is what keeps it from being too much.
I think of this as a dinner outfit, the kind of place with dim lighting and small plates. Slip the blazer off if the room warms up. The whole point is the contrast between soft sheer fabric and hard structured shoulders.
Silver Mini Dress With Kitten Heels
A short silver dress with a low, sensible kitten heel is such a smart combination. The dress is playful and a little bit party, and the low heel keeps you standing all night without wanting to sit down.
I am not a tall-heel person anymore, I will not lie to you. So this look, sparkly on top and comfortable on the bottom, is exactly my speed for a night out that involves any amount of walking.
Light Blue Slip Dress With Lace Trim
A slip dress with a little lace edge at the neckline is the sweetest thing. In a pale blue it feels calm and pretty and just a bit vintage.
This light blue dress outfit is one I would wear to a garden party or a daytime celebration. The lace trim adds a small detail that makes the whole dress feel considered. A pair of beige sandals and a soft cardigan and you are dressed.
Denim Shirt Dress With Statement Belt
The shirt dress is one of those pieces that goes from truly casual to actually polished depending on what you do with it. In denim, it’s practical. Add a big statement belt and cinch the waist and suddenly it’s an outfit.
I wear mine buttoned most of the way with the belt over top, sneakers for errands or heeled sandals for a lunch date. So easy. The belt does all the heavy lifting here, so pick one you love.
Floral Drop-Waist Dress With Mary Janes
Drop-waist dresses are back and I could not be happier because they hide everything I want hidden. In a small floral print with a pair of Mary Janes, this look is a little bit retro and a lot cute.
My daughter borrowed mine for a school photo thing last spring and now it lives in her room, which is fine, I have accepted it. The Mary Janes make it feel schoolgirl-in-a-good-way, and it photographs like a dream.
Gold Bodycon Dress With Sculptural Heels
Okay, this one is for the big nights. A fitted gold bodycon dress hugs everything and a sculptural, architectural heel turns it into a proper statement.
You need confidence for this and not much else. Small earrings, hair pulled back, and let the dress and the wild shoe be the entire conversation. In fact, the less you add here, the more expensive it looks.
Sheer Floral Dress Over Matching Shorts
And to close it out, my favorite easy trick: a sheer floral dress worn over a matching set of shorts underneath. You get the movement and the pretty of a sheer dress with none of the worry.
This flower dress outfit is what I live in during the hottest weeks of summer. Flat sandals, a straw bag, and I feel breezy and covered at the same time. The shorts underneath mean I can chase after the kids or sit on the ground and not think twice about it.
