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    Chicago News Journal
    Home»LifeStyle

    5 Expensive-Looking Transitional Outfits to Take you Into Autumn

    AdminBy AdminAugust 10, 2026 LifeStyle
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    I’m currently in the process of turning my spare room into a walk-in wardrobe (yes, it’s the viral IKEA PAX hack) so a mass cleanse is happening. But as a fashion editor with a lot of clothes, I’m still having to prioritise the pieces I’ll be wearing most over the next few months. The only issue is, while summer is still in full swing, autumn is fast approaching, so is it best to focus on shorts and cami tops or knitwear and jackets? The answer: both.

    The awkward time between summer and autumn can be tricky to navigate, but it’s all about merging the seasons together with cleverly layered looks that don’t fully sit in one seasonal box. To further explain what I mean, I took it upon myself to get some transitional outfit inspiration from some of the most stylish women I follow. The outcome is five outfits, all of which will serve us well throughout this time. Think drummer jackets with jeans and sandals, oversized jumpers with sporty shorts and flip flops. Meanwhile, key pieces—including a shirt, a cropped trench and the humble T-shirt —are coming into full fruition. Here are the effortless outfits to copy over the next few weeks using items you most likely already have in your wardrobe.

    5 Summer-to-Autumn Transitional Outfit Ideas to Copy in 2026

    1. Cropped Trench + Satin Top + Balloon Trousers

    Hannah wearing trench coat

    Style Notes: If we have to be back in jackets, they should be a worthy addition to our outfits—right? A cropped trench is the perfect style to bridge the gap between seasons, and I love how Hannah has elevated hers with volume and texture in the form of balloon trousers with satin and suede.

    Latest Videos FromWho What Wear

    Shop the Look:

    Double-Breasted Cropped Trench Coat - Women | Mango United Kingdom

    MANGO

    Double-Breasted Cropped Trench Coat

    To get Hannah’s oversized look, size up once, or even twice.

    Topshop Satin Scoop Neck Cami With Fringe Detail Tie in Ivory

    Topshop

    Satin Scoop Neck Cami With Fringe Detail Tie

    I’ve just ordered this Topshop top with the tassel tie—too cute.

    Gathered Cotton Balloon Trousers

    COS

    Gathered Cotton Balloon Trousers

    If you’re not ready to swap summer shorts for jeans, voluminous balloon pants are the answer.

    Tabi New Ballerina Split-Toe Patent-Leather Ballet Flats

    MAISON MARGIELA

    Tabi New Ballerina Split-Toe Patent-Leather Ballet Flats

    Massimo Dutti, Ruched Split Suede Leather Bag

    Massimo Dutti

    Ruched Split Suede Leather Bag

    It’s time to dig out your suede accessories.

    2. Long Sleeve T-Shirt + Short Sleeve T-shirt + Midi Skirt

    Nnenna wearing T-shirt

    Style Notes: Clever layering is Nnenna’s speciality, and this time, she’s focused on stacking tops. This micro trend was already huge in summer, but now it’s coming through to autumn too, and it’s such an easy way to adjust to the changing temperatures without instantly swaddling up in a jacket or coat.

    Shop the Look:

    Roya Cashmere V-Neck

    Reformation

    Roya Cashmere V-Neck

    Since CPHFW, we all know aqua is set to be major.

    Clean Cut T-Shirt

    Cos T-shirts always have the best weight.

    Pleated Midi Skirt - Beige

    & Other Stories

    Pleated Midi Skirt

    I’ll also be wearing this with a check shirt come autumn.

    Café Mini Leather Shoulder Bag

    VERAFIED

    Café Mini Leather Shoulder Bag

    Verafied is one of my favourite mid-price bag brands.

    Calista Scrunch Heel

    Reformation

    Calista Scrunch Heel

    The ruched detail—love!

    3. Jumper + Sporty Shorts + Flip Flops

    Aimee wearing jumper and shorts

    Style Notes: I’ll forever love the look of autumn on top, summer on the bottom. Whether it’s a knit and sporty shorts (as seen above on Aimee) or a jacket zipped up with a skirt, it’s the perfect formula for the midst of this in-betweeny time of year.

    Shop the Look:

    Aran Jumper - Oat Milk

    Slow Love

    Aran Jumper Oat Milk

    The cosiest knit by British label, Slow Love.

    The Boyfriend: Tencel™ Lyocell, Off-White

    With Nothing Underneath

    The Boyfriend

    Make sure to pop the collar like Aimee.

    Logo-Embroidered Jersey Shorts

    SPORTY & RICH

    Logo-Embroidered Jersey Shorts

    I want the matching track jacket, too.

    Aviator Sunglasses - Brown - M

    2026 sunglasses = the bigger the better.

    Leather Straps Sandals - Women | Mango United Kingdom

    MANGO

    Leather Straps Sandals

    I’ll be wearing flip flops until the weather tells me not to.

    4. Fitted Shirt + Canvas Jacket + Utility Trousers

    Annabel wearing shirt and trousers

    Style Notes: This is one of those looks I would happily wear to the office. Mixing shirting with relaxed utility pieces, I’ll forever back the power of a shirt layered over a vest top, and 18-year-old me, who didn’t leave the house without a statement necklace of some kind, is so glad they’re back.

    Shop the Look:

    & Other Stories, Oversized Drawstring Utility Jacket

    & Other Stories

    Oversized Drawstring Utility Jacket

    The drawstring waist is key.

    Arket, Cotton Poplin Shirt

    Arket

    Cotton Poplin Shirt

    Pink and green will always be a firm favourite.

    Asos Design Thick Binding Rib Scoop Neck Vest in White

    ASOS DESIGN

    Thick Binding Rib Scoop Neck Vest

    The humble white vest will stick around well into autumn.

    Liana Silver Plated Tassel Necklace in Silver

    Rixo

    Liana Silver Plated Tassel Necklace in Silver

    Tassel necklaces are everywhere right now—this Rixo x Billie Bhatia style is on my wish list.

    Shon Cotton Twill Barrel-Leg Pants in Green - Nili Lotan

    Nili Lotan

    Shon Cotton Twill Barrel-Leg Pants

    5. Drummer Jacket + Jeans + Sandals

    Dawn wearing jacket and jeans

    Style Notes: The hat, the drummer jacket, the jeans with just the right amount of slouch—Dawn has indeed nailed the brief. Looking polished from top-to-toe, I’m already packing away my summer shorts to copy this look (albeit with a warm-weather appropriate sandal).