Looking good in the cold can be hard! Which is particularly annoying when you want to look your best. That’s why we’ve gathered 21 of our favorite fall date outfits to help inspire your next date fit!
When putting together a fall look, keep the weather in mind and dress appropriately, especially if you’ll be outdoors. Think about how the materials and colors work together and, as always, pay attention to the cut and fit of items.
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1. Sweater and a dress
Throwing a minidress on over a sweater is a simple and classic formula that is always good to have in your back pocket. Adding hose or tights underneath add some warmth and and we think it adds something to the look. Knee high boots, heels, flats, or loafers would all look great with this choice.
2. Leather shorts
Leather shorts are somewhat unexpected pick for fall date outfits, but we think they’re styled well here with an elegant off the shoulder top and boots. If it’s colder where you live, try adding some hose to the look for an extra layer!
3. Sleeveless sweater and jeans
For fun daytime dates, it’s hard to go wrong with a good pair of jeans and a sleeveless knit sweater. If it’s a bit chillier, throw a blazer on top like shown in this example. It’s the perfect option for fall days with unpredictable weather and is highly adaptable to your personal style.
4. Autumn Americana
We had to include this Ralph Lauren sweater for as one of our more casual fall date outfits, it’s just so casually cool! The sweater is obviously the star of the show, but the leather jacket and bag add interest to up the look a bit. Uggs are pretty divisive, so if they’re up your alley, go for it, if not, loafers, sneakers, or ankle boots would be great options.
5. Chic black on black
All black is a cheat code for those dates where you don’t know what to wear. In general, monochromatic looks will always look more elevated, so you could also replicate this in another color! The form fitting off the shoulder top balances well with the more voluminous jeans for a look that is popular right now, but feels a bit more elevated.
6. Sweater and a mini skirt
We have another sweater option for our fall date outfits, but this time paired with a denim miniskirt for a flirty option that’s highly customizable. With this particular sweater, the look reads a bit sporty, but by opting for a different cut and style you can alter the look to suit your tastes!
7. Statement trench
Spring and fall are trench coat seasons! Leaning into outerwear as a statement is a perfect way to look chic and put together in the colder seasons. This is a fairly simple outfit, but the luxe suede trench coat takes it to a whole new level! Don’t overlook jackets and coats as statement pieces; fun colors, interesting patterns, or unexpected materials can all take a trench from good to great.
8. Shearling coat
Next we have another outfit that is amped up by a coat, but this time it’s a shearling coat. The mix of materials of the coat adds visual interest and the classic style lends outfits an effortlessly chic effect to your fall date outfits!
9. Off the shoulder sweater dress
There is something so elegant about a sweater dress! The form fitting cut and off the shoulder neckline that bares just enough skin to give the look a sensual ease without trying too hard. Knee high leather boots are our favorite shoe choice for this look, but heels are a great option for warmer fall weather.
10. Trench coat and heels
We can’t emphasize enough how impactful outerwear is on your fall outfits! Once again, a coat has elevated a very straightforward outfit. The long lines and folds of the trench coat makes the outfit look a bit dressier, which is perfect for fall date outfits! The heeled sandals are great for warmer days, but the look would also work with knee high boots, ankle boots, sneakers, or loafers.
11. Comfy and casual
Whether you’re going to a coffee shop, going to a pumpkin patch, or visiting a fall festival, having a good set of casual fall date outfits for daytime activities is key! This option isn’t rocket science, it’s a sweater, jeans, and Uggs. However, the key is in the details! The fit and chunky knit of the sweater, the cut of the jeans, the choice of shoes and socks. Dial these in and you’ll have a cute and laidback daytime date option.
12. Satin midi and a coat
For those occasions where you need a more formal option, a satin skirt provides an excellent foundation. Pair the skirt with a well fitted top and add a classy outerwear piece, and you get one of our favorite fall date outfits. With such a simple formula, make sure the fit of each item is good and the materials are high quality for maximum impact!
13. Effortless sweater vest
Sweater vests are having a moment, and we are fully on board! Sweater vests have a classic feel and add a third layer to the look, which will often look more intentional and put together. Opt for a sweater vest in a neutral that suits you for an elegant effect or a fun color or pattern to make a statement!
14. Knee high boots
This is probably on of the easiest fall date outfits to put together, so keep this in mind next time you have nothing to wear! Find an oversized sweater or a looser sweater dress and pair it with some knee high heeled boots for a cute fall option. If you’re worried about getting cold, you can add some panty hose to keep your legs warm.
15. Wrapped statement sweater
A sweater wrapped around your shoulders adds detail to a simple look, that third element we mentioned earlier! It classes up an outfit without looking like you’ve tried too hard, it’s effortlessly elegant. Opting for a bold color like red or blue will kick up the excitement in an otherwise non-descript outfit.
16. Lug sole boots
We’ve seen a fair number of sweaters in our fall date outfits so far, but this one features a new player: lug sole boots. The sweater and miniskirt create a flirty and feminine foundation with the lug sole boots toughening it up a bit in a fun and unexpected way. The boots ground the look, making it less formal and a great way to stay comfortable and cute for an outdoor date.
17. Leopard print skirt and blazer
Leopard print will always be in style in our world! But it also happens to be trending right now in the fashion realm. The flow of the satin midi contrasts beautifully against the structure of the blazer for an elegant date outfit option!
18. Warm layers
Cold weather is fun because you dive head first into layering! The next of our fall date outfits really capitalizes on layers, but in a stylish way perfect for dates. A leather jacket layered over a chunky knit sweater provides an interesting material contrast, you can add a shirt beneath the sweater for an yet another layer! Boot socks emerge from the riding boots, adding to the layered effect. The plaid mini coordinates well with the color palette, pulling it all together!
19. Cozy blanket scarf
We’ve spoken at length about the importance of outwear, but our focus was mostly on jackets and coats. Don’t overlook scarves, especially if you live in a colder climate. A large blanket scarf in a bold pattern or coordinating color can easily add interest to your date look and make you look chic even in the cold weather.
20. Oversized leather jacket
The miniskirt and top combo is a date outfit staple, particularly because it’s so adaptable to different seasons and situations. To add this look to your repertoire of fall date outfits, add tights and an oversized leather jacket. Knee high riding boots are both cute and great for walking during the day, for night time you can opt for heeled boots or whatever suits your fancy!
21. Ribbon and ballet flats
Ballet flats and a ribbon in your hair will give you a coquettish, romantic look for your date, particularly when paired with a color coordinated off the shoulder sweater. Jeans complete the look for a simple and feminine choice for your next fall date!
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