6 Tips From Fashion Stylist On How To Wear A Dress In The Fall

How to wear a dress in the fall
Photo: Jose Martinez / Unsplash

When fall arrives around and temperatures become colder, it can be challenging to style a dress when you need to keep warm at the same time. Many save dresses for summer months, keeping pants and jeans for fall months, but it doesn’t need to be this way!

If you want to know the best ways to rock a dress in the fall months, keep reading. We’ve researched the best style tips to keep you feeling on-trend this autumn while embracing dresses. Why limit yourself to trousers when you can still wear skirts and dresses?

RELATED: 8 Fall Trends To Avoid in Autumn 2021, According to Stylists

Here are our top tips for styling dresses in the fall!

How To Wear A Dress In The Fall

Tip #1: Keep The Summer Dress Alive

Just because summer is over doesn’t mean you have to instantly forget about your summer dresses!

While many categorize their wardrobes by season, it’s actually a good idea to wear summer clothes in winter and just layer them up. This keeps your wardrobe versatile and also adds more variety to your outfit options. Mixing and matching clothes is a great way to add variety to your daily outfit rotations.

Though summer dresses tend to be lighter and brighter in color than those popular for fall months, you can still strategically style them to meet an autumnal color palette.

For example, take a light summer dress and pair it with a darker jacket for a balanced color look. Dark denim jackets or leather jackets are great for pairing with summer dresses. Another great option is an oversized cardigan. These are great for the fall months and look cute when paired with some leather boots too.

Tip #2: Ditsy Florals Work Well In Autumn

Though floral dresses are commonly associated with spring and summer, wearing ditsy florals can be very effective in fall.

This styling tip is specifically about smaller floral prints rather than large abstract varieties, as these fabrics can look dainty and feminine. This is a great way to add some print and pattern into your fall wardrobe by adding playful touches to a usually dark palette.

Popular styles of fall floral dresses are maxi and mini lengths, as well as dresses with puffy or gathered sleeves. This “milkmaid” style pairs well with ditsy florals, giving a very feminine look that works well when contrasted with a dark-colored coat and accessories. When styling these dresses, try pairing them with pearl jewelry or crystal pendant necklaces.

You may have seen these on social media, as this has been a popular trend with influencers over the past few seasons.

Tip #3: Pair It With Long Boots

Long boots are coming back into fashion with a vengeance.

Whether you opt for an extreme thigh-high pair or chic knee-length shoes, these are great for pairing with fall dresses. If you’re wearing a midi or mini-length dress, long boots can add a touch of style to the outfit. Playing around with different types of footwear can be a great way to switch up your outfits without buying more clothes.

Heeled knee-high boots in black or chocolate brown with dresses in autumnal colors are always a winning combination when it comes to fall street style. With a dress and boots, you have an outfit for daytime fashion and evening events. Just accessorize accordingly! 

Tip #4: Embrace A Vintage Style

Another key trend to trial when it comes to fall dresses is adopting a vintage look. The most popular decades to try are the 60s and 70s. Fashion bloggers and influencers have been embracing these styles for fall recently, and we think it’s a style everyone should try once. You never know, you could find your inner retro babe persona!

For a 60s look, try pairing a darker-colored dress with white boots and a beret. The dress can really be any style, but try to go for an orange, beige, or burgundy color. The darker dress shade will contrast the white boots, and the outfit will instantly look retro.

Chunky earrings and bold eyeliner also look great with this style, perfect for anyone who wants to take fall fashion in a unique direction. You can also play with tartan or check print dresses too. These instantly give off a vintage vibe and always fit in well with fall fashion.

Tip #5: Try Decorative Tights

A common reason many stop wearing dresses in the autumn months is because they find it too cold. We have a fashionable solution to this problem, and that is to try decorative tights! These tights are always popular in fall and make a great alternative to standard black or skin-colored tight options.

Photo: fashionmylegs.blogspot.com

Instead of pairing dresses with plain black pantyhose, a pair of patterned tights can make a world of difference to your style and transform the look of the dress.

Go from basic to chic with your casual dress and a new pair of tights. Key patterns to try are polka dot styles. These have a french-chic element and match most dresses.

If your fall dress is pattern-heavy, it might be better to stick to plain tights. However, if you have a more simple dress go bolder with the tights. Experiment to find the style that matches your dresses best!

Tip #6: Keep The Outfit Monochrome

While you can wear any color in any season, it is best to embrace an autumnal palette in fall. This means embracing darker colors such as greens, reds, oranges, and browns. Pops of gold, silver, and purple also work well too.

These colors have always been popular for this season as they mimic the darker days and the look of nature in general at this time of the year. When the trees are turning yellow and red, why not match them?

Photo: sedbona.com

One of the best ways to nail this palette look is with a dress! Wearing a block color dress and matching your accessories and shoes to the same hue is a great way to dress in one color. This fall dress style will keep you looking coordinated and will totally embrace the autumn vibe.

Dressing in a monochrome outfit is always a great choice. This saves time when getting ready in the morning, too, as there’s no stress about matching different colors – perfect for busy mornings.


As the fall is here, will you be trialing these dress tips for the colder months? Hopefully, our recommendations have given you some style inspiration and advice for wearing dresses in the fall.

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