đź–¤ 10 Kendall Jenner Outfits Street Styles

ByJenna Dempsey

Let’s raid Kendall’s imaginary closet without the PR emails. Think sleek silhouettes, quiet-luxury basics, and a dash of cool-girl chaos. We’re mixing model-off-duty ease with runway polish. Ready to strut the sidewalk like it’s a soft-launch catwalk?

1. Oversized Blazer with Micro Tee

Corporate on top, concert in spirit. The balance is all clean lines and a flash of midriff.

  • Items: boxy oversized blazer, cropped white tee, straight-leg denim, pointed slingbacks
  • Textures: matte wool, crisp cotton, sleek leather

Styling tip: Push the blazer sleeves and add skinny sunglasses to sharpen the silhouette.

It works because the structure skims the body while the tee keeps it playful and effortless.

2. Monochrome Athleisure Set

Like you just left Pilates but somehow got photographed. Cozy, toned, unstoppable.

  • Items: matching ribbed set, crew socks, chunky dad sneakers, baseball cap
  • Textures: rib knit, soft cotton, rubber soles

Styling tip: Layer a cropped puffer or trench to elevate from gym to street.

Monochrome elongates the frame and reads intentional, not gym-lost.

3. Leather Trench and Tiny Tank

Minimal top, maximum drama. The coat does all the talking, you just smirk.

  • Items: long leather trench, fitted white tank, tailored trousers, square-toe boots
  • Textures: glossy leather, smooth jersey, suiting wool

Styling tip: Keep jewelry thin and metallic to echo the trench hardware.

The contrast of sleek and simple delivers modern polish without trying hard.

4. Sheer Top with High-Waist Trousers

See-through but chic. Confident, not costume.

  • Items: sheer black top, minimal bralette, pleated trousers, kitten heels
  • Textures: gauzy mesh, satin trim, soft wool

Styling tip: Tuck the top and anchor with a slim belt for waist definition.

It strikes the perfect tease-to-tailored ratio for city nights.

5. Moto Jacket with Ballet Flats

Punk meets prim and they hold hands. A little edge, a little twirl.

  • Items: cropped moto jacket, baby tee, mid-rise jeans, ballet flats
  • Textures: pebbled leather, soft cotton, satin or glove leather flats

Styling tip: Choose a red flat for a micro-pop that still reads luxe.

The clash keeps it interesting while staying wearable all day.

6. Trench Coat over Hoodie

Rainy-day romance with a street brain. Cozy, sleek, camera-ready.

  • Items: classic trench, neutral hoodie, leggings or slim cargos, chunky sneakers
  • Textures: gabardine, fleece, technical nylon

Styling tip: Let the hoodie peak at the hem and hood for layered dimension.

High-low layering makes the trench feel young and unfussy.

7. Slip Dress with Big Boots

Delicate dress, tough stomp. Angel energy with a backstage pass.

  • Items: bias-cut slip, oversized cardigan or bomber, combat or lug-sole boots
  • Textures: liquid satin, chunky knit, rubber tread

Styling tip: Add a thin choker or hoop earrings to bridge soft and strong.

The contrast keeps the slip from feeling precious and adds attitude.

8. Double Denim but Tailored

Canadian tuxedo, but make it fashion week. Clean lines, sharp fades.

  • Items: fitted denim shirt, straight or barrel jeans, belt, pointed boots
  • Textures: rigid denim, burnished leather

Styling tip: Slightly different washes add depth without clashing.

Tailoring turns a classic into a sleek, model-off-duty uniform.

9. Tube Top with Oversized Trousers

Airy up top, drama below. Balance that says yes-I-meant-that.

  • Items: knit tube or bandeau, wide-leg trousers, minimalist sandals, micro bag
  • Textures: rib knit, fluid twill, smooth leather

Styling tip: Cinch with a slim belt and keep hair slick for clean lines.

Volume play keeps the silhouette modern and effortless.

10. Cardigan as Top with Mini

Grandpa sweater, supermodel agenda. Buttoned just-so.

  • Items: cropped cardigan, mini skirt, sheer tights, Mary Janes or loafers
  • Textures: soft cashmere, structured wool, glossy patent

Styling tip: Add a shoulder bag with a short strap for that off-duty nip-tuck.

Sweet meets sleek, and the proportions feel fresh and flirty.

Conclusion

Kendall’s street style is a masterclass in clean lines, sharp contrasts, and comfy swagger. Build around strong basics, tweak textures, and keep everything intentional. If it walks like confidence and lounges like sweats, you nailed it.

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