What Not to Wear If You’re Hourglass: 5 Fall Outfit Swaps from an Hourglass Fashion Founder

August 14, 2025

Hourglass shape style guide what to wear and skip

Ready for some hard-earned truth from a fellow hourglass? I’ve been styling my own curves since before LookSky was even an idea. At 5'0", with a defined waist, fuller bust, and balanced hips, I’ve learned that certain “trendy” pieces look incredible online but do nothing for me in real life.

Here’s the good news: dressing an hourglass shape isn’t about hiding anything. It’s about highlighting what you already have. The trick is knowing which cuts and fabrics love your curves — and which ones fight them.

LookSky is your favorite online clothing store — but smarter. We match you to outfits that work for your body, your color season, and your vibe. And with virtual try-on, you can preview each look on your actual proportions before buying — no more guessing, no more costly mistakes.

What’s the best way to dress an hourglass shape?

LookSky shows you exactly which pieces work for your curves — so you try on only what fits before you commit. Cinched waists, balanced proportions, and fabrics that move with your body are key.

Skip: Boxy, Waistless Dresses

Swap for: Fitted Belted Midis

Why the swap works:

• Straight cuts erase your waist and make your frame look wider.

• Cinched silhouettes follow your natural curves without clinging.

• A-line skirts balance your bust and hips.

LookSky Picks:

• Nate Dress from Petal and Pup

• Karen Dress from Sézane

Try It On in LookSky: See how the waistline hits your body before you buy — even one inch too high or low changes everything.

Skip: Low-Rise Jeans

Swap for: High-Waisted, Contoured Denim

Why the swap works:

• Low-rise cuts shorten the leg line and draw focus to the hips.

• High-rise jeans elongate your silhouette and define your waist.

• Contoured waistbands prevent gapping in the back.

LookSky Picks:

• Wilder High Rise Wide Leg Jeans from Reformation

• Val 90s Mid Rise Straight Jeans from Reformation

Try It On in LookSky: Check waistband height on your avatar to make sure they shape — not flatten — your curves.

Skip: Drop-Shoulder Tops

Swap for: Fitted or Structured Shoulders

Why the swap works:

• Drop shoulders make the upper body look boxy.

• Fitted or slightly padded shoulders balance the bust and hips.

• Creates a proportional frame for layering.

LookSky Picks:

• Maxine Tank from Marcella NYC

• Flutter V-Neck Super Soft Tee from Torrid

Try It On in LookSky: Preview shoulder seams to see if they align with your natural shoulder line — it’s the difference between polished and sloppy.

Skip: Shapeless Oversized Blazers

Swap for: Fitted or Peplum style Single-Breasted Outerwear

Why the swap works:

• Oversized cuts swamp your frame and hide your shape.

• Peplum styles keep your waist defined even over layers.

• Single-breasted designs elongate the torso.

LookSky Picks:

• Red Peplum Button Front Blazer from River Island

• Celia Linen Blend Jacket from Object Rare

Try It On in LookSky: Adjust belt placement in virtual try-on to see if it sits on your natural waist — not your ribcage.

Skip: Shapeless, Straight Skirts

Swap for: Flared or Pencil Skirts with Stretch

Why the swap works:

• Straight skirts fight your curves and can cause pulling at the hips.

• Bias cuts drape over your shape naturally.

• Stretch pencil skirts hug without squeezing.

LookSky Picks:

• Silk Asymmetric Wrap Skirt by Grana

• Retro Chic Pencil Skirt by Torrid

Try It On in LookSky: Test skirt movement and see if the hem rides up when you walk — you’ll know before you check out.

Skip List for Hourglass Shapes

• Dropped waists (hide your natural waistline)

• Chunky cable knits without shaping

• Ultra-wide palazzo pants without a fitted top

• Cropped boxy jackets

From the Founder

“As a fashion founder with an hourglass figure, I believe you should always wear what you love. But I also know how frustrating it is to spend money on clothes that don’t work. We built LookSky to empower you to do both — embrace your style while knowing every piece will fit, flatter, and make you feel amazing.” — Samantha Shih, Co-Founder of LookSky

Apps like Daydream or Gensmo might inspire you with moodboards — but they won’t show you exactly how a dress will drape over your curves. LookSky lets you see it on your body before you buy.

[Yes! Show Me What Works for My Shape]

You Might Also Like:

• 7 Fall Wedding Guest Dresses from Revolve for Your Shape — Try Before You Buy (Not Gensmo or Daydream) — From satin slips to belted midis, see which cuts flatter your curves.

• You Don’t Have to Show It All to Flaunt Your Shape: 5 Hourglass Outfits That Aren’t Tight or Try-Hard

• The Best Summer Dresses for Hourglass Figures (Or Anyone Who Wants That Vibe)

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