I bought my first deep red dress on a whim, in a little shop my sister dragged me into on a rainy Saturday afternoon. I did not need it. I told myself I did not need it. And then I wore it three times that same week.
There is something about a good dress that just makes getting ready easier. One piece, done, out the door. But the fun part, honestly, is all the ways you can style the same dress and have it feel like a completely different day.
So I started keeping a little running list in my phone of dress combinations I love. Below are 20 of my favorites.
20 Ways to Style a Dress You Already Own
Burgundy Dress With Knee-High Boots
This is the combination that started my obsession. A burgundy dress outfit paired with tall leather boots feels rich and autumnal without any effort at all. The deep red against the brown boots is just so pretty.
I wore this to a lunch last October and my friend Dana asked me where I got the dress before I even sat down. That’s a good sign.
Burgundy Satin Dress With Blazer
Take that same deep red, but in a satin fabric, and throw a structured blazer over the top. The shine of the satin and the sharpness of the blazer balance each other out beautifully.
This is my go-to for anything work-adjacent where I still want to look like myself. A dinner out. A nicer meeting. That kind of thing.
White Slip Dress Over Blue Jeans
Now here is where it gets fun. A dress over jeans outfit sounds odd until you actually try it, and then you never look back. A simple white slip dress layered over straight blue jeans looks so cool and a little bit unexpected.
I was skeptical, I will not lie to you. But my sister does this constantly and always looks great, so I copied her. Of course I did.
Beige Knit Dress With Suede Boots
A soft beige knit dress with suede boots in a matching tone is the coziest thing you can wear when it’s chilly out. Everything in the same warm neutral family, top to bottom.
This is the outfit I reach for when I want to be comfortable but still feel put together, which honestly is most days.
Navy Dress With Brown Leather Boots
Navy and brown is one of those color pairings that always looks intentional even when you throw it together in two minutes. A navy dress with brown leather boots reads classic and a little bit preppy.
Add a leather bag in the same brown and you’re done.
Pinafore Dress With Striped Tee
A pinafore dress over a striped tee is one of those looks that feels playful and grown-up at the same time. The stripes peek out at the neckline and the sleeves and add a little Parisian touch.
I love this for weekend antiquing or a casual coffee date. It looks like you tried, even though you really didn’t.
Aesthetic Maxi Dress With Sneakers
A long, flowy maxi dress paired with clean white sneakers is the definition of comfortable and easy. You can walk all day in this and never once think about your feet.
I wore something like this on a walking day in the city two summers ago and hit a very high step count without ever wanting to sit down. A dress and sneaker combo will do that for you.
Burgundy Dress With Leopard Flats
If you want a little edge, swap out your plain shoes for leopard print flats. Against a deep red dress, the print acts almost like a neutral, which sounds strange but it’s true.
Leopard is one of those prints that just always looks chic, and it wakes up a simple dress in the best way.
Denim Shirt Dress Over Straight Jeans
A denim shirt dress worn open over straight jeans gives you that double-denim look without feeling like too much. Leave the buttons undone and let it act like a long jacket over your jeans and a tee.
This is such a laidback, run-around outfit. Farmers’ markets, weekend errands, dropping the kids at practice. It just works.
Beige Linen Dress With Raffia Bag
For the warmer months, a beige dress outfit built around a breezy linen dress and a raffia bag feels like a little vacation. The natural textures of the linen and the raffia go together so nicely.
Add flat sandals and oversized sunglasses and you could be strolling somewhere by the water. Or, in my case, walking to the grocery store pretending I’m somewhere by the water.
Navy Slip Dress With Ballet Flats
A navy slip dress with ballet flats is quiet and elegant and takes almost no thought. The slip dress does all the work and the flats keep it soft and walkable.
I like a little gold jewelry with this to add a hint of glam.
Pinafore Dress With Turtleneck
When it gets colder, layer a fitted turtleneck under your pinafore dress. The turtleneck adds warmth and a little polish, and the pinafore keeps it feeling youthful and fun.
Cream turtleneck under a dark pinafore is my favorite version. So cozy for those grey winter mornings.
Aesthetic White Dress With Cardigan
An aesthetic dress outfit doesn’t have to be complicated. A pretty white dress with a soft cardigan tossed over the shoulders is about as easy as it gets, and it photographs beautifully too.
I keep a cream cardigan by the door for exactly this reason. It goes over almost everything and instantly makes an outfit look finished.
Burgundy Dress With Camel Coat
Deep red and camel is one of those combinations that just feels expensive. A long camel coat thrown over a burgundy dress is the outfit I daydream about when the first cold day arrives.
The colors are warm and rich together, and a camel coat is one of those pieces you’ll reach for again and again for years. Worth every penny, in my opinion.
Dress Over Jeans With Pointed Heels
Here’s the dressed-up version of the layered look. A dress over jeans with pointed heels takes something casual and makes it feel a little more polished, perfect for an evening out.
The heels lengthen everything and stop the outfit from reading too relaxed. It’s a nice trick when you can’t decide how fancy you’re supposed to be.
Beige Midi Dress With Loafers
A beige midi dress with loafers is such a smart, tidy look. There’s something about a loafer that makes any outfit feel a bit more intentional, a bit more grown-up.
I wear this a lot in early fall when it’s still warm enough for a midi but I want closed shoes. It’s become one of my most reliable combinations.
Navy Dress With Oversized Blazer
Take a navy dress and drop an oversized blazer over the top for that borrowed-from-someone-else feeling. The blazer being a little too big is exactly the point.
I stole this idea from my husband’s actual blazer once and I have to say, it looked better on than I expected. Never told him though.
Pinafore Dress With Knee-High Boots
A pinafore dress with tall knee-high boots is such a good cold weather outfit. The boots cover your legs and the pinafore gives you that fun, layered shape on top.
Add tights underneath and you’ve got something you can wear well into winter. Warm and cute, which is the goal.
Aesthetic Floral Dress With Cowboy Boots
A floral dress with cowboy boots is unexpected in the best way. The sweetness of the flowers against the western boots gives the outfit a little bit of attitude, a little bit of fun.
My friend wears this to outdoor concerts and she always looks so cool. I keep meaning to copy her and one of these days I actually will.
Burgundy Dress With Statement Belt
Last one, and it’s a simple one. Cinch a deep red dress at the waist with a wide statement belt and suddenly a plain dress has shape and structure. A belt is such an easy way to change the whole feeling of a dress.
I keep a couple of belts in different widths just for this. Same dress, different belt, completely different look. It almost feels like cheating.
