I used to stand in front of my closet way too long every morning, half-dressed, moving hangers around and getting nowhere. My sister Jenna, who has a curvier frame than me and always looks put together, finally sat me down one Sunday and walked me through her whole approach.
And to be completely honest with you guys.. It changed a looot! She wasn’t telling me to hide anything. She was showing me how to work WITH my shape instead of against it.
So I started collecting the combinations that made me feel good, the ones I reached for again and again.
20 Outfit Combinations I Come Back to Over and Over
Wrap Top With High-Waisted Wide-Leg Jeans
This is the first thing I show anyone who asks me how to dress for your body type, because a wrap top just does the work for you. It cinches at the smallest part of your waist and then flows, and it never feels like it’s clinging in a spot you don’t want it to.
Pair it with high-waisted wide-leg jeans and you get this long, easy line from your chest all the way to your shoes. I wore this to a lunch with Jenna last month and felt like a million bucks the entire time.
Fitted Bodysuit With Straight-Leg Trousers
A fitted bodysuit is my secret weapon on days when I want a clean, tucked-in look without any of the tucking. It stays put. Nothing rides up. Nothing bunches.
Add straight-leg trousers and you’ve got something that reads polished enough for the office but still feels comfortable. So easy.
Oversized Blazer With Bodycon Midi Dress
Okay, hear me out on this one. A bodycon midi dress on its own can feel like a lot for an everyday outing, but throw an oversized blazer over it and suddenly it’s this balanced, confident look. The blazer softens the fitted lines and adds structure at the shoulders.
I love the contrast of soft and structured. It’s the kind of outfit that looks like you tried harder than you actually did.
Peplum Top With Flared Jeans
Peplum tops get a bad rap and I will not lie to you, some of them are cut terribly. But the right one, the kind that flares gently just below the waist, is genuinely one of the most flattering things I own.
With flared jeans the whole silhouette becomes this lovely hourglass. It’s a little retro, a little playful, and it just WORKS.
Button-Down Shirt With Denim Midi Skirt
Sometimes you want to look like you have your life together even when you don’t. A crisp button-down shirt tucked into a denim midi skirt does that for me every single time.
I leave the top couple of buttons open and roll the sleeves. Add a belt if you want a little more definition at the waist.
Cropped Cardigan With High-Waisted Jeans
A cropped cardigan sounds intimidating but it’s really not, especially with high-waisted jeans. The trick is that the cardigan hits right at the top of the waistband, so you get this flattering, elongating effect without showing any midsection you’d rather keep covered.
My friend Dana talked me into buying my first one and now I own three. Butter yellow is my favorite.
Belted Shirt Dress With Knee-High Boots
The belted shirt dress is a hero piece for medium size body outfits and honestly for any body, because that belt lets you decide exactly where your waist sits. You get to draw the line yourself.
Add knee-high boots and the look goes from Sunday errands to dinner in about two seconds. I’ve done this in fall so many times I’ve lost count.
Tank Top With Drawstring Pants
This is my lazy day uniform and I’m not ashamed of it. A fitted tank top, tucked or half-tucked, with soft drawstring pants that you can adjust to whatever feels good that day.
Comfort with just a splash of polish. And drawstrings are so forgiving, which is exactly why I keep buying more of them.
Denim Jacket With Black Maxi Dress
A black maxi dress is basically a blank canvas, and I mean that as the highest compliment. It skims, it flows, it hides absolutely nothing that needs hiding and everything you want it to.
Throw a denim jacket over the top and you break up all that black with something casual and easy. I wore this to an outdoor thing over the summer and stayed comfortable the entire evening.
Square-Neck Top With A-Line Skirt
Square necklines are so underrated. They frame your collarbones and shoulders in this really pretty way, and they feel a little more interesting than a plain round neck.
With an A-line skirt that skims out from the waist, you get a shape that’s feminine and forgiving all at once. This is one I reach for when I want to feel put together.
Fitted T-Shirt With Cargo Pants
Cargo pants came back and I, for one, am thrilled. Paired with a fitted t-shirt, they give you this cool, laid-back energy without any effort at all.
The fitted top balances out the roomier pants. If everything is baggy it can look like you’re swimming in fabric, so I like one fitted piece against one relaxed piece.
Longline Vest With Wide-Leg Trousers
A longline vest adds these gorgeous vertical lines that just make you look taller and leaner without doing anything. It’s almost like a little optical trick.
With wide-leg trousers underneath, the whole outfit feels intentional and a bit fashion-forward. I felt very cool the first time I wore this combo, I’ll admit it.
Off-Shoulder Top With Bootcut Jeans
Off-shoulder tops show a little skin in the most flattering place, right across the shoulders and collarbone. It draws the eye up and it’s just a pretty neckline.
Bootcut jeans balance the whole thing out at the bottom. There’s something about this pairing that feels breezy and a little romantic, honestly.
Wrap Dress With Block Heels
If I could only keep one dress it might be a wrap dress. It ties at the waist, it adjusts to you, and it does that beautiful diagonal line across the body that everyone loves for a reason.
Block heels finish it off and they’re actually walkable, which matters to me because I am NOT a stiletto person. Never have been.
Tucked-In Sweater With Pleated Midi Skirt
Here’s a cozy one for the cooler months. A soft sweater tucked into a pleated midi skirt gives you warmth and shape at the same time, and the pleats add this lovely bit of movement when you walk.
I do a loose front tuck so nothing feels too tight around the middle. Add tights and boots and you’re set for the whole day.
Leather Jacket With Barrel-Leg Jeans
Barrel-leg jeans are the trend I resisted the longest and then fell completely in love with. They curve out and taper in, which is such an interesting shape.
A leather jacket on top adds edge and structure through the shoulders. This is the outfit I wear when I want to feel a little tougher than I actually am, if I’m being honest.
Bandeau Top With Palazzo Pants
For warm weather, a bandeau top with flowy palazzo pants is dreamy. The pants are so airy and forgiving, they move with you and never cling.
I usually add a light open shirt over the bandeau for a little coverage. That way the outfit works for lunch and for an evening stroll both.
Babydoll Dress With Knee-High Boots
Babydoll dresses flow out from just under the chest, which means they float over everything below and just feel FREEING to wear. No waistband digging in anywhere.
Pairing them with knee-high boots grounds the softness and keeps the look from feeling too girlish. It’s a combination I stole from a photo I saw and never looked back.
Blazer With Bermuda Shorts
Bermuda shorts hit at the knee, so they give you more coverage than short shorts while still keeping you cool. And a tailored blazer over the top makes them look surprisingly dressy.
This is my answer to warm-weather workwear, or brunch, or really any daytime thing where I want to look like I made an effort.
Ribbed Midi Dress With Denim Jacket
A ribbed midi dress is one of those pieces that skims the body in the gentlest way. The ribbing has a little stretch and structure so it holds its shape without feeling constricting.
I toss a denim jacket over it for daytime and take it off for the evening. Two outfits in one, which is exactly the kind of thing my busy self appreciates.
