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8 transitional dresses to wear with boots and tights in autumn 2023

These versatile transitional dresses can be worn all year round


collage four dresses
Sophie Bates
Commerce Writer
Updated: August 31, 2023
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It's that time of year again when the weather just can't make up its mind. From sudden downpours to stuffy offices, it can be hard to predict which way the wind blows. 

We're thinking about those timeless transitional pieces that work for each and every season – and we're starting with dresses. One of the easiest ways to build up a capsule collection is to add the kinds of dresses that can be accessorised with trainers in the sunshine or tights and boots in the cooler months. 

How to style a transitional dress

Transitional dresses can be styled with trainers and sandals in the warm months, but they will look just as great teamed with a pair of chunky boots and leather jacket during the autumn and winter months. Darker colours are super versatile for styling for a new season, although florals and vibrant prints can still work perfectly with your autumn accessories.

How we chose the best transitonal dresses

  • Variety: From mini dresses to floral midi dresses, I've selected a variety of styles to suit plenty of preferences and occasions. 
  • Price: I've chosen transitional dresses with a range of price points, from affordable high-street styles to luxury pieces. 
  • Trusted brands: All the brands I've chosen are ones HELLO! team swears by. We've not tried on all of the products but the brands are some of our favourites, so the quality should be high.

Shop the best transitional dresses for the new season 

  • nobodys child black floral midi dress

    Nobody's Child Floral Dress

    Dark florals are the perfect transitional style, and Nobody's Child's midaxi dress ticks all the boxes. It features a V-neck, elegant balloon sleeves and an under-bust seam designed to flatter the figure - while the black dress perfectly contrasts the red poppies print. 

  • and other stories printed midi dress

    & Other Stories Relaxed Printed Dress

    & Other Stories is filled with staple dresses for the new season. The sweetheart printed dress has puffed sleeves with frilled cuffs, a square neckline and a gathered bust, complete with a side slit on the relaxed skirt. The elegant style can be dressed up or down, and we love it teamed with a pair of white strappy heels.

  • marks and spencer printed midi dress

    M&S Printed Sweetheart Dress

    Marks & Spencer's printed midi dress is so feminine with its sweetheart neckline and shaping shirred panel across the front. Finished with gathered short sleeves and a floaty skirt, the tea dress would look just as stylish teamed with a cropped leather jacket and black heeled boots in autumn as it would styled with a denim jacket and a pair of Veja trainers.

  • new look black mini dress

    New Look Jersey Smock Dress

    Looking for a shorter transitional style? New Look's black mini dress is the one. Designed with crinkle jersey fabric, the smock silhouette looks super comfortable, tying in at the waist for an enhanced silhouette. The tie neckline rounds off the effortless look, and we'd recommend styling the dress with a pair of cowboy boots for a 'cool girl' festival look, and swapping them out for a pair of chunky biker boots and a longline coat as the weather gets colder.

  • h and m black bodycon dress

    H&M Ribbed Midi Dress

    H&M's knitted dress is made with a ribbed design and a figure-skimming fitted silhouette. The sweetheart neckline and lightly flared sleeves give it a feminine finish, and the black dress will make a flattering staple for all year round. The transitional dress is available in sizes XS-4XL, with black and burgandy versions, too.

  • karen millen navy shirt dress

    Karen Millen Midi Shirt Dress

    Karen Millen has put an elevated twist on the shirt dress with its sheer midi. The navy frock features an underdress while leaving a sheer finish on the skirt and sleeves, tying in at the waist with the matching belt. Finished with a contrasting white trim, the dress will make for an amazing day-to-night piece through the seasons.

  • asos black tea dress

    ASOS Tea Midi Dress

    Featuring puff sleeves, a plunge neckline and a front split, ASOS's collared tea dress will look so stylish teamed with a pair of Birkenstock sandals or black ankle boots and an oversized jacket during the day, and we'd reccomend opting for a pair of lilac strappy heels to level up the look for the evening.

  • asos denim midi dress

    River Island Denim Midi Dress

    Denim dresses have been a top fashion trend for 2023, and River Island's version is perfect for seeing you through the change of seasons. The dark denim works for summer and autumn, with long sleeves for those colder evenings. It's available in sizes 6-18 – and we love it styled with a pair of cream heeled boots.

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