I own seven cutout dresses. I’ve also made every mistake you can make with them — visible adhesive wings, a bra strap that photobombed every group shot, and one unfortunate evening where the cutout sat so high on my ribs it looked like I was wearing a corset from a Halloween store. After years of trial and error (and one very patient tailor), here’s what I’ve learned.
Cutout dresses are polarizing. You either love the peek-a-boo effect or you’re convinced they’re a styling trap. I’m here to tell you: they work, but only if you nail three things — the cutout placement, the undergarment strategy, and the silhouette balance. Ignore any one of those and the look falls apart.
The Three Cutout Placements That Actually Flatter
Not all cutouts are created equal. The difference between “effortlessly cool” and “please adjust your dress” comes down to where the fabric disappears.
Side waist cutouts — the safest bet
These sit just above your natural waist, usually on both sides. They create an hourglass illusion without exposing anything delicate. Reformation’s Delilah dress ($248) does this perfectly — the cutouts are narrow (about 3 inches wide) and sit high enough that your hip bone stays covered. I’ve worn this to three weddings and never once felt exposed.
The trick: side cutouts work best when the dress has some structure elsewhere. If the rest of the dress is bodycon, the cutout reads as intentional. If the dress is loose everywhere, the cutout looks like a tear.
Keyhole back cutouts — the office-appropriate option
A single vertical cutout at the center back, from between your shoulder blades to mid-spine. It’s the most forgiving placement because it doesn’t affect how bras or shapewear sit. Aritzia’s Wilfred Free Posse Dress ($110) has a keyhole back that falls exactly at bra-line level — the band of a standard bra sits just above the opening, so nothing peeks out.
This is the cutout placement I recommend for anyone who’s nervous about the trend. You get the visual interest without the wardrobe malfunction anxiety.
Asymmetric shoulder cutouts — the trickiest to pull off
One shoulder covered, one shoulder bare, with a cutout at the collarbone or upper arm. These look amazing in photos but are a nightmare with bags — every purse strap slides directly into the opening. Zara’s Asymmetric Cutout Midi Dress ($79) is the most affordable version I’ve tested, but the cutout sits 2 inches lower than shown on the model. Buy one size up and have a tailor move the strap 1 inch inward.
If you carry a crossbody bag, skip this silhouette entirely. Clutches only.
Bra Solutions for Every Cutout Location (No, You Don’t Need to Go Braless)
This is the number one question I get. “How do I wear a bra with this thing?” The answer depends on where the cutout is, and the answer is almost never “just go braless” — unless you genuinely prefer that.
| Cutout Location | Best Bra Solution | Price Range | Why It Works |
|---|---|---|---|
| Side waist | Low-back converter + regular bra | $12–$20 (converter clip) | Keeps your normal bra, moves the band down 3–4 inches |
| Keyhole back | Adhesive cups (e.g., Nubra Feather Lite) | $45 | No band to interfere with the vertical opening |
| Asymmetric shoulder | Convertible strapless bra (e.g., Spanx Bra-llelujah) | $68 | Wear one strap, hide the other, or go strapless entirely |
| Chest/cleavage cutout | Adhesive silicone cups + fashion tape | $30–$50 (Nubra or Skims) | No straps, no band — just cups that stick to your skin |
| Backless (large cutout) | Skims Backless Bra ($32) | $32 | Self-adhesive front coverage, wraps around your ribcage below the cutout |
I’ve tested all of these. The Spanx Bra-llelujah ($68) is the only strapless I trust for a full night of dancing — it stays put even after three glasses of wine and a humid dance floor. The Nubra Feather Lite ($45) is my go-to for backless situations, but wash them by hand after every wear or the adhesive loses grip within 6 months.
One thing I never do: rely on fashion tape alone to hold up a regular bra. Tape peels off after 2 hours of body heat. Get the right bra.
The One Silhouette Rule That Prevents 90% of Cutout Dress Disasters
Here’s the rule I swear by: one focal point at a time. If the dress has a dramatic cutout, the rest of the silhouette should be simple. If the dress has an unusual shape (puff sleeves, asymmetrical hem, extreme slit), the cutout should be minimal.
I broke this rule exactly once. I wore a H&M Conscious Cutout Midi ($59) that had both a side waist cutout AND a thigh-high slit AND a ruched bodice. The result was a dress that competed with itself. Every element was fighting for attention, and from across the room it just looked chaotic.
What works: a column silhouette with a single side cutout. A sheath dress with a keyhole back. An A-line midi with an asymmetric shoulder cutout. Pick one surprise element and let the rest of the dress recede.
This also applies to accessories. If the cutout is at the waist, skip a belt. If the cutout is at the shoulder, skip statement earrings — the dress is already making the statement.
When NOT to Buy a Cutout Dress (and What to Get Instead)
I know this sounds counterintuitive for an article about wearing them, but there are situations where a cutout dress is the wrong choice. Here’s when I’d tell you to skip it entirely.
You’re attending a formal event with a strict dress code
Black tie and white tie events have unspoken rules about skin exposure. A cutout dress at a gala reads as casual, no matter how expensive it is. Instead, get a dress with a plunging neckline or an open back — same level of intrigue, but the silhouette is more formal. Reformation’s Sienna Dress ($278) has a deep V back that shows skin without a literal hole in the fabric.
You’re going somewhere with unpredictable temperature
Cutout dresses are terrible for transitional weather. A side cutout at an outdoor fall wedding means a cold draft directly on your ribs for 4 hours. If you’re going to be outside in under 70°F, choose a dress with strategic cutouts that can be covered by a blazer or shawl. Keyhole back works. Side waist does not — blazers sit right on top of the opening.
You’re planning to eat a large meal
This is the honest truth no one tells you. A cutout at the waist or ribcage expands visibly when you sit down and eat. I learned this the hard way at a three-course dinner wearing a Bodycon Cutout Dress from Aritzia ($150). By the main course, the cutout had stretched from a 2-inch slit to a 4-inch gap. The fabric didn’t snap back until I stood up. If dinner is the main event, wear a dress where the cutout is on the back or shoulder — places that don’t change shape when you’re seated.
How to Style a Cutout Dress for Day vs. Night
The same dress can look completely different depending on how you style it. I own a Skims Fits Everybody Cutout Midi ($96) that I’ve worn to brunch and to a cocktail party. The difference is in the details.
Daytime styling
Layer it. A white button-down tied at the waist, an oversized blazer, or a denim jacket worn open — all of these partially cover the cutout and make it feel intentional rather than provocative. Pair with flat sandals or white sneakers. The goal is to downplay the sexiness of the cutout by surrounding it with casual pieces.
I wear my Skims dress with a Aerie Oversized Blazer ($79) and white Veja sneakers. The cutout peeks through when I move, but the overall vibe is “I just threw this on” — which is exactly the look I want for daytime.
Nighttime styling
Go all in. Heels, dramatic jewelry, a sleek clutch. Let the cutout be the centerpiece. For evening, I avoid any layering that covers the cutout — the whole point is the reveal. I add a thin gold chain belt ($35 from Mejuri) to draw the eye toward the cutout and create a deliberate focal point.
The one thing I never do at night: add a jacket. If you need a jacket, the dress isn’t right for the venue.
The Three Biggest Mistakes People Make (and How to Avoid Them)
I’ve seen these mistakes at parties, on Instagram, and on myself. Learn from them.
Mistake #1: The cutout is in the wrong place for your body
A cutout at the widest part of your hips makes your hips look wider. A cutout at the smallest part of your waist creates an hourglass. This sounds obvious, but I’ve seen countless women buy a dress because the cutout looked good on the model, not because it worked for their proportions.
Measure your torso before buying. If you have a short torso, avoid cutouts at the natural waist — they’ll sit closer to your ribs and look like a midriff cutout instead. If you have a long torso, cutouts at the waist are perfect because they hit exactly where they should.
Mistake #2: Visible shapewear edges
Cutout dresses and high-waisted shapewear are enemies. If the cutout is at the waist, your shapewear will show at the edges. Solution: wear smoothing shorts that end below the cutout, or a bodysuit that starts above it. Spanx Suit Your Fancy Bodysuit ($98) has a deep V back that works with most back cutouts, and the bottom snaps are low enough to stay hidden under a midi dress.
Mistake #3: The wrong fabric weight
Cutouts need structure. A flimsy jersey knit will sag and gape around the opening. A ponte knit, scuba fabric, or double-lined crepe holds the cutout’s shape. When I shop, I press the fabric around the cutout with my thumb — if it wrinkles or buckles, I put it back. Reformation’s linen-blend cutout dresses ($248–$298) are the exception: the linen is stiff enough to hold shape but breathes better than synthetics.
My rule: if the dress costs under $80 and has a cutout, the fabric is probably too thin. Save up or skip it.
One Dress, Three Ways — My Go-To Cutout Dress Formula
If you buy one cutout dress this year, make it a midi-length, side-waist cutout, in a neutral color (black, navy, or olive). That dress will work for at least three different occasions with minimal styling changes.
I own the Aritzia Wilfred Free Only Dress ($130) in black. Side waist cutouts, crew neck, sleeveless, midi length. Here’s how I wear it:
- Office: With a cropped blazer (covers the cutouts entirely), pointed flats, a structured tote. The cutouts are hidden, but the silhouette still feels modern.
- Date night: No blazer, strappy heeled sandals, a thin chain belt at the waist, earrings that don’t compete. The cutout is the focus.
- Weekend brunch: White sneakers, an oversized denim jacket unbuttoned, a crossbody bag. The cutout peeks through when I move, but the overall look is relaxed.
That’s the real secret to wearing a cutout dress. It’s not about being brave or showing skin. It’s about having one dress that adapts to your life, not the other way around.
I still have the disaster dress from my first cutout attempt — the one with the high ribcage cutout that looked like a costume. It hangs in my closet as a reminder. These days, I reach for the dresses that let me forget I’m wearing a cutout at all. That’s when they work best.