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  • New
    Plus Size Checked Vest Plus Size Pants Suit Matching Set Millennium Checked Vest

    Matching Set

    Millennium Checked Vest - Black White

    Polished, precise and made to work hard. This Millennium checked vest features a tailored, elongated design with refined button detailing for a structured cut. Designed to be worn solo or paired with the matching pants for a cohesive two-piece set, it delivers a modern...
    $59.50
    $0.00
    $59.50
      13
    • Black White
  • New
    Plus Size Checked Vest Plus Size Pants Suit Matching SetMillennium Checked Ankle Pants

    Matching Set

    Millennium Checked Ankle Pants - Black White

    Tailored with intent & cut for modernity. These Millennium ankle pants are crafted in checked twill for a clean, structured fit with just enough ease for all-day wear. Sitting at the ankle for a sharp finish, they’re designed to pair seamlessly with the matching...
    $54.50
    $0.00
    $54.50
      43
    • Black White
  • New
    Millennium Embellished JacketMillennium Embellished Jacket

    Matching Set

    Millennium Embellished Jacket - Pink

    Sharp, sleek and just a scoop of extra, this Millennium jacket is finished with bold gold buttons that mean business. Wear it alone or pair it with the matching pants for a full boss moment.
    $59.50
    $0.00
    $59.50
      13
    • Pink
      • 73
    • Black
  • New
    Millennium Sailor PantsMillennium Sailor Pants

    Matching Set

    Millennium Sailor Pants - Pink

    Structured lines, confident energy & major main character aesthetic, these Millennium sailor pants feature gold buttons that instantly update the look. Style them solo or pair with the matching jacket.
    $54.50
    $0.00
    $54.50
      13
    • Pink
      • 73
    • Black
  • New
    Button Detailed Crepe JacketButton Detailed Crepe Jacket

    Matching Set

    Button Detailed Crepe Jacket - Nasturtium

    Polished, poised, and undeniably chic, our stretch-crepe jacket is the epitome of quiet luxury. Designed with sleek tailoring and two faux flap pockets, it’s all about effortless sophistication.
    $49.50
    $0.00
    $49.50
      13
    • Nasturtium
  • New
    Pleated Crepe ShortsPleated Crepe Shorts

    Matching Set

    Pleated Crepe Shorts - Nasturtium

    These crepe shorts are a masterclass in understated luxury. The tailored fit and pleated detailing create a polished silhouette, perfect for stepping out in style.
    $39.50
    $0.00
    $39.50
      13
    • Nasturtium
  • New
    Square Neck Chambray VestSquare Neck Chambray Vest

    Matching Set

    Square Neck Chambray Vest - Brown

    This chambray vest is cut with a square neck for a sharp, minimal feel that still reads easy, not rigid. Wear it with the matching pants for a head-to-toe denim moment.
    $59.50
    $0.00
    $59.50
      23
    • Brown
  • New
    Chambray Wide Leg PantsChambray Wide Leg Pants

    Matching Set

    Chambray Wide Leg Pants - Brown

    Laid-back, but not careless. These chambray wide-leg pants bring a relaxed drape finished in a soft brown wash that keeps things grounded. Pair them with the matching vest for a chic set that feels simple, but never basic.
    $64.50
    $0.00
    $64.50
      63
    • Brown
  • New
    Printed Button Front Cropped ShirtPrinted Button Front Cropped Shirt

    Matching Set

    Printed Button Front Cropped Shirt - Blue

    Look like you belong somewhere with palm trees and cold drinks nearby. This printed crepe de chine cropped shirt keeps things light with an easy shape and elasticized waistband that gives it that casually tucked feel without the effort. Wear it with the matching...
    $18.00
    $39.50
    $18.00
    Online Exclusive
      13
    • Blue
      • 43
    • Green
      • 73
    • Natural Leopard
  • New
    Watercolor Floral Print ShirtWatercolor Floral Print Shirt

    Matching Set

    Watercolor Floral Print Shirt - Multi

    Watercolor florals set the tone on this linen-like woven shirt, cut with side splits for a relaxed fit. Pair it with the matching shorts for an easy two-piece set made for long summer days.
    $54.50
    $0.00
    $54.50
      13
    • Multi
  • New
    Watercolor Floral Print ShortsWatercolor Floral Print Shorts

    Matching Set

    Watercolor Floral Print Shorts - Multi

    Watercolor florals bring a soft, summery feel to these mid-rise woven shorts designed in a linen-like texture with crisp pleats. Pair them with the matching shirt for a coordinated two-piece set.
    $54.50
    $0.00
    $54.50
      23
    • Multi
  • New
    Palm Print Linen Blend ShirtPalm Print Linen Blend Shirt

    Matching Set

    Palm Print Linen Blend Shirt - Teal

    Palms print sways across a soft linen-blend fabric. This shirt pairs with the matching skirt for a warm weather two-piece set.
    $54.50
    $0.00
    $54.50
      13
    • Teal
  • New
    Palm Print Linen Blend SkirtPalm Print Linen Blend Skirt

    Matching Set

    Palm Print Linen Blend Skirt - Teal

    Lightweight, relaxed and full of character. This palm print midi skirt teams up with the shirt for a flirty, head-turning set.
    $54.50
    $0.00
    $54.50
      13
    • Teal
  • Plus Size Yellow Blazer Plus Size Jacket Plus Size Three Piece Suit SetMillennium Button Front Blazer

    Matching Set

    Millennium Button Front Blazer - Canary Yellow

    Get straight to business in our posh Millennium stretch-twill blazer that can be worn as a suit with the matching skirt or trousers.
    $25.00
    $64.50
    $25.00
      33
    • Canary Yellow
  • Plus Size Yellow Trousers Plus Size Suit Plus Size Pants Two Piece SetMillennium Straight Leg Trousers

    Matching Set

    Millennium Straight Leg Trousers - Canary Yellow

    Back to business in fabulous fashion thanks to our Millennium mid-rise trousers cut into a straight-leg fit from stretch-twill.
    $25.00
    $54.50
    $25.00
      23
    • Canary Yellow
  • Cowl Neck Crepe CamiCowl Neck Crepe Cami

    Matching Set

    Cowl Neck Crepe Cami - Amazon

    An easy piece you’ll keep reaching for. This crepe cami features a soft cowl neckline that falls just right without trying too hard. Wear it on its own or pair it with the matching kimono when you want it to feel a little more...
    $18.00
    $39.50
    $18.00
      13
    • Amazon
      • 153
    • Pansy
  • Open Front Crepe KimonoOpen Front Crepe Kimono

    Matching Set

    Open Front Crepe Kimono - Amazon

    Just throw it on and go. This crepe kimono keeps it easy with an open front and a fluid drape that works over just about anything. Pair it with the matching cami when you want it to feel a little more put together.
    $18.00
    $54.50
    $18.00
      193
    • Amazon
  • Millennium Buttoned BlazerMillennium Buttoned Blazer

    Matching Set

    Millennium Buttoned Blazer - Black

    Get straight to business in our posh Millennium stretch-twill blazer that can be worn as a suit with the matching skirt or trousers.
    $25.00
    $64.50
    $25.00
      13
    • Black
  • Millennium Pocket Front SkirtMillennium Pocket Front Skirt

    Matching Set

    Millennium Pocket Front Skirt - Black

    $20.00
    $44.50
    $20.00
      13
    • Black
  • Millennium Pull On TrousersMillennium Short Pull On Trousers

    Matching Set (Short)

    Millennium Short Pull On Trousers - Black

    Sleek, polished, and made to flatter, these Millennium stretch-twill trousers feature a comfortable mid-rise fit, slant pockets, and an easy pull-on design. The streamlined straight-leg silhouette delivers effortless, curve-loving confidence from office hours to after hours.
    $25.00
    $54.50
    $25.00
      13
    • Black
  • Millennium Pull On TrousersMillennium Pull On Trousers

    Matching Set

    Millennium Pull On Trousers - Black

    Sleek, polished, and made to flatter, these Millennium stretch-twill trousers feature a comfortable mid-rise fit, slant pockets, and an easy pull-on design. The streamlined straight-leg silhouette delivers effortless, curve-loving confidence from office hours to after hours.
    $25.00
    $54.50
    $25.00
      13
    • Black
  • Millennium Pull On TrousersMillennium Tall Pull On Trousers

    Matching Set (Tall)

    Millennium Tall Pull On Trousers - Black

    Sleek, polished, and made to flatter, these Millennium stretch-twill trousers feature a comfortable mid-rise fit, slant pockets, and an easy pull-on design. The streamlined straight-leg silhouette delivers effortless, curve-loving confidence from office hours to after hours.
    $25.00
    $54.50
    $25.00
      13
    • Black
  • Millennium Button Front BlazerMillennium Button Up Blazer

    Matching Set

    Millennium Button Up Blazer - White

    Get straight to business in our posh Millennium stretch-twill blazer that can be worn as a suit with the matching skirt or trousers.
    $25.00
    $64.50
    $25.00
      23
    • White
  • Millennium Twill Pencil SkirtMillennium Twill Pencil Skirt

    Matching Set

    Millennium Twill Pencil Skirt - White

    $20.00
    $44.50
    $20.00
      13
    • White
  • Millennium Straight Leg TrousersMillennium Straight Leg Trouser

    Matching Set

    Millennium Straight Leg Trouser - White

    Back to business in fabulous fashion thanks to our Millennium mid-rise trousers cut into a straight-leg fit from stretch-twill.
    $25.00
    $54.50
    $25.00
      23
    • White
  • New
    Plus Size Chevron Wide Leg Pants Zig Zag Knit Pants SetChevron Knit Wide Leg Pants

    Matching Set

    Chevron Knit Wide Leg Pants - Caribbean Sea

    Chevron knit, wide-leg & style that showcases your personality. The fit is relaxed but still feels intentional with just enough colors & dimension to catch attention. Wear them solo or lock in the full set with the matching top.
    $54.50
    $0.00
    $54.50
      13
    • Caribbean Sea
  • New
    Open Front Ruffled JacketOpen Front Ruffled Jacket

    Matching Set

    Open Front Ruffled Jacket - Lime Green

    Ruffles are soft but still boss on this slightly abbreviated jacket with ruffles fluttering along the edges. We love it paired the wide-leg capris.
    $44.50
    $44.50
    Online Exclusive
      13
    • Lime Green
      • 83
    • Blue
  • New
    Pleat Detailed Wide Leg CaprisPleat Detailed Wide Leg Capris

    Matching Set

    Pleat Detailed Wide Leg Capris - Lime Green

    Pleats are pleasing on our wide-leg capris layered with our ruffled jacket.
    $44.50
    $0.00
    $44.50
    Online Exclusive
      13
    • Lime Green
      • 83
    • Blue
  • New
    Pleated Wide Leg CaprisPleated Wide Leg Capris

    Matching Set

    Pleated Wide Leg Capris - Black

    Pleats are pleasing on our wide-leg capris layered with our ruffled jacket.
    $44.50
    $0.00
    $44.50
      23
    • Black
      • 93
    • White
  • New
    Ruffled Open Front JacketRuffled Open Front Jacket

    Matching Set

    Ruffled Open Front Jacket - White

    Ruffles are soft but still boss on this slightly abbreviated jacket with ruffles fluttering along the edges. We love it paired the wide-leg capris.
    $44.50
    $44.50
      43
    • White
      • 83
    • Black

Recently Viewed Products

Look Fabulous & Office Chic In Our Workwear Sets

Designed for style, comfort and versatility, Ashley Stewart has the best & trendiest two-piece sets to revamp your work attire. Take the guesswork out of putting together a polished look with our options that allow you to mix & match colors, patterns & fabrics without skipping a beat. Coordinate blazers & skirts for a monochromatic look, or mix blouses & pants for fun contrasting prints. Leave the morning stress behind you as our two-piece wear-to-work sets ensure that you're dressed to impress in no time, making your morning routine easy! Whether you’re looking for the perfect outfit pairing with leggings or a pencil skirt, these two-piece outfits will make a statement with plaid prints, faux leather, and power-suit options. Perfect for business casual offices as well as more professional attire, mix-and-match blazers, dress pants, pencil skirts or midi skirts to keep updating your looks throughout the week. Upgrade your workwear game with Ashley Stewart’s plus-size workwear sets. The convenience of coordinated outfits matched with the versatility of mix and match will make you feel cool & confident, ready to win at work. Explore our collection today and experience the perfect combination of fashion and professionalism.

Shop Plus Size Clothing Online or In-Store

Find our Work Wear Sets collection online or find an Ashley Stewart location near you.