10 Stylish Transitional Outfits to Elevate Your October Wardrobe

Surprisingly, October dressing is tricky. In theory, you break out some good trousers, some cosy knit sweaters or two, and a good jacket and you should be OK. The month, however, is one of such weather variations that in any one day you might be dressing for warm and cold temperatures. However, ‘fall’ dictates certain elements of an outfit—a ‘fall’ outfit is something that depends on your preferred temperature and the local weather.

Co-founder and head designer of Wild Rose & Sparrow, Ariana Dancu, said that this month layering is key since you can add more layers or fewer. She adds, “I live in Montreal so I know what transitional outfits are; you can’t really be warm and it certainly doesn’t mean you can just copy and paste what other people say are fall outfits and be comfortable anywhere.”

01. Light Layers

If you already like layering, great news: This is a fall when you can go really wild. Amani Saab, co-founder and head designer of Amani Saab, recommends lightweight cardigans, sweaters, denim jackets and shawls that are easy to remove when you put on your layers.

If you want to layer without it looking too bulky or uncomfortable, layer a thin layer on top of your outfit of choice. “Late September: A crisp white shirt and my soft mohair sweater vest are one of my favourite combos,” says co-founder and chief creative director, Maj La Pizzelli.

02. On-Theme Colors

Saab suggests adding in the season with the colors worn: ‘Wear lighter pieces like blouses or skirts in that incorporate autumnal colors like burgundy, olive green or brown.’ “That’s why classic fall colors like burgundy, plum, and chocolate really pair so well with building fall vibes even if the pieces of clothing aren’t necessarily meant for cold weather,” Dancu adds. Something like this tee-shirt and shorts combo would be good for summer, but with that burgundy cardigan and knee-high socks, it’s more for fall.

03. Fall Textures

If fall colors aren’t your thing, then you can still bring a cool weather vibe by pulling in texture. A subtler way to ease into fall is adding accessories made of warmer fabrics such as leather, suede and wool for shoes, belts and hats. Saab also points out that the same concept works for footwear: switch from sandals to boots to get into the fall aesthetic when it’s not really winter yet. In this case, the chunky shoes, brown bag and matching sunglasses give solid substance to this flowy look.

04. A Statement Jacket

A truly great jacket is a safe bet for October (and really, fall in general) when in doubt. A timeless staple piece that will even bring out the best in a basic shirt and jeans.” You can easily build or embark on a tailored blazer without altering your overall appearance and light enough to pack up in case it heats up.” Said Saab.

According to head designer and founder Sensi Studio, a good coat is a must-have this season. “I have such a good investment to have a trench coat in different materials in; you just throw on that: ‘I have that trench coat, and that is one of the pieces in your wardrobe that you have to invest in.’ I also adore Jane Birkin—midi fur coat á la zipper basket. This summery outfit gets a major fall upgrade with a long suede jacket and a big bag.

05. Invest in Your Knits

One thing fall is good for, if there’s ever one. Knits. You can wear them alone in cool-but-not-cold weather, or you can throw one over an outer layer. But I love layering cashmere in general because it is lightweight, breathable and ultra soft. “You can even pieces like cashmere dresses so good for this because they are so warm and you can just put tights and a sweater or jacket on top,” explains Dancu.

So if you like knits, of course, it’s free to go all in like with this three-piece matching set.

06. A Cool Hat

What I really love is when your headpiece is substantial and doesn’t have to do much to look really comfortable in the cooler months. A cool hat is a great accessory, I think. It may be a dark straw hat to cosy them up, and couple it with cool pompoms to make it fun. Another amazing option, says Sensi, is a felted wool hat that lends character and is weather-appropriate. ‘I’m a fan of the cowboy-shaped felted hat for your weekend getaway,’ she says. If a structural hat feels too much, opt for a baseball cap instead.

07. A Big Tote

Cool weather means bigger bag. Despite the heat outside, “nothing says ‘beginning of fall’ like a classic suede loafer or a big bag,” La Pizzelli says. “They are just big totes that are so chic and polished and they put you in the fall mode, and they allow you to bring a sweater or something, or if the temperature just kind of goes haywire.” Added benefit is that this is a red-burgundy fall color. Instead, tie a sweater around your neck!

08. A Neutral Base Layer

Saab says opting for a monochromatic look in a neutral base like black, navy, beige or grey adds polish to any look. “You can just go and play with the textures and also just use fancy materials like cashmere, silk and leather to curate for you a cohesive look that lets you mix and match everything in a nice vibe, really.” The base layer is a light grey and goes well with both the green bag and jacket so you can also opt for a neutral base layer if you want cooler, more daring (or less daring) accessories.

09. Going With a Mini

It doesn’t mean covered up while layering. You will still be able to wear your hemlines lower in October. A mini skirt or dress will be fine with an oversized sweater and Western boots and finish it off with a sharp, flat slingback, says Saab, describing it as ‘the hero trans-seasonal.’ La Pizzelli adds, “Summer in the back, fall in the front!” A slingback like the above is pretty cool, and if you slightly loom out the dress hemline, this would be a good look for work.

10. Pick a Blazer Dress

Saab particularly likes a blazer dress (with tall boots). Next she explains the blazer dress ‘for a sleek, structured, sophisticated silhouette… the over-the-knee boots give a little drama, but keep you warm.’ So, it’s not a tonne of legs, but it still manages daring. So although this is a cool ‘throw on and go’ outfit, (you can see here) it’s also quite easy to add some shorts or a skirt underneath for something a little more coverage.

Conclusion

When October’s weather changes, having the right transitional outfits can all add up. These 10 stylish looks will make you comfortable and at the same time help you to style during the season change. Take advantage of the layers, explore texture and enjoy the versatility of these pieces as you shift to cooler days. As you start wearing these outfit ideas, you’ll be prepared for whatever October decides to throw at you weather-wise.