30 Fall Outfit Ideas for Every Occasion This Season

Fall is finally here and your calendar is filling up, but what are you going to wear to all of the social engagements you have planned this season, not to mention at work? Don’t worry; I’ve got you covered with 30 fashionable fall outfit ideas to keep you looking good until winter. Check out my fall outfit inspiration to take the guesswork out of getting dressed this season.

Fall Outfit Ideas

1. New Job || Got a new job this fall? Impress your colleagues with this chic look: a long, patterned skirt with a coordinating blazer and a crisp white shirt.

2. Hold onto Summer || I hate the “no white after Labor Day” rule, especially on a hot September night. Is the weather still warm where you live? Try a white crossbody bag and this eye-catching asymmetrical top.

3. Desk to Dinner || Turn heads at the office with this form-flattering sheath dress—professional and stylish enough to take you from desk to dinner!

Fall Outfit Ideas

4. Meetings in the City || Technically, summer doesn’t end until September 20th, so rock this chic wrap linen top and stylish slacks with a little bling to set it off.

5. Drinks with the Girls || After work, head out for the night with these cool culottes paired with a silk, blousy shell and chunky, heeled booties.

6. Date Night || Nothing says Friday night like a hot asymmetrical little bodycon dress. The subtle cutouts are sexy, and this number is probably all the skin you will show until next summer.

Fall Outfit Ideas

7. Weekend Chic || This casual, silk denim print dress is a unique way to sport a fashionable jean look.

8. Dinner and Drinks || Grab your favorite jumpsuit and throw on some pumps for a night out! Jewel tones are perfect for fall, and this teal off-the-shoulder piece pairs perfectly with these purple pumps.

9. Work Lunch || This versatile red print top can be worn almost anywhere this fall; however, a crop tuxedo-style pant and metallic heels are a smart work look.

Fall Outfit Ideas

10. Big Presentation || Nothing says fall like a sweater dress, and this fitted Herve Leger is professional yet eye-catching for that next big presentation you have at work.

11. Downtown Vibes || As the weather turns chilly this fall, a versatile blazer will be your best friend. This windowpane print option doubles as a lightweight jacket this season and looks great with jeans and booties.

12. Art Gallery Opening || The possibilities are endless with this three-quarter-sleeve, cheetah-print maxi dress with a split. This gorgeous dress is perfect with a slingback heel or cool Western-inspired boot.

Fall Outfit Ideas

13. Interview || Leave the blazer at home, because this stylish corporate outfit is perfect for an interview. Paired with a silk print top, these trendy burgundy-colored pants will help you get the job.

14. Weekend Brunch || Weekends are made for brunching! Try wearing some distressed denim with an a-line top and some comfortable flats, and you will be dressed for anything that comes your way!

15. Business Conference || Nothing says “I mean business” like a sleek neckline. This fitted yet professional number is perfect for fall with some high boots to add a bit of style to the look.

Fall Outfit Ideas

16. Fashion Show || Fall is all about fashion, so show up to your next fashion event like you are in the know! This sexy turtle sweater dress with a high split offers the best of both worlds this season.

17. Saturday Night Drinks || Animal print for the win! Head out on Saturday night with this chic black sweater with silk animal-print sleeves, dark denim, and black booties.

18. Broadway Show || Curtain call! The show you been dying to see awaits, so be sure to dress for the occasion. Keep the animal print going with this leopard-print dress, and be sure to bring a jacket, as the theaters can get chilly.

Fall Outfit Ideas

19. Casual Friday || Work or play, Fridays are always a bit more casual. Go gray with denim, boots, and this plaid blazer—and finish off the look with clean white.

20. Concert Vibes || You got tickets to the hottest show in town, so dress like you should be in the front row! Nothing says concert like ripped jeans and a fun sleeveless top.

21. Happy Hour || Every hour can be a happy one with this cute color-blocked sweater dress. If the night is chilly, you can always throw on some tights to keep your legs warm.

Fall Outfit Ideas

22. Dinner with the In-Laws || Sensible and stylish are key when meeting the parents. This knit a-line skirt looks polished with a matching top and a leather jacket that can be worn indoors or as outerwear.

23. Bar Hopping || Bring out the leather pants—it’s time to hit the bars! Leather is always a fun choice, so let loose on the dance floor, toast to good company, and laugh the night away in this number. These pants pair great with a flowy top or something silk.

24. Office Party || Consider this stylish leather look for work. This flattering leather skirt is certainly work appropriate, especially when you wear it with a turtleneck sweater and understated accessories.

Fall Outfit Ideas

25. Errands Around Town || Stay stylish and warm while you are running around town. Running errands can be chilly business, especially if you are doing so on foot! A cable-knit sweater, leggings, and over-the-knee boots equal fall perfection.

26. Parent/Teacher Conferences || Whether you’re the parent or the teacher, a modern blazer, dark jeans, and combat boots are the perfect choice. Be sure to pair this number with a layered necklace for some extra flair.

27. Evening at Home with Friends || Call your friends over and have a glass of wine on a cool fall day with this cozy sweater, pants with a pop of color, and cool flats.

Fall Outfit Ideas

28. Birthday Party || Cute, flirty, and fun, this fall floral dress is perfect for celebrating an evening out with friends, and these suede over-the-knee boots make the outfit fall fabulous.

29. Elegant Cocktail Party || A chic one-shoulder top and statement necklace is the perfect combination for a night of wine and spirits, and dark pants like these are totally acceptable for the occasion.

30. Fall Festival || Get ready to pick some pumpkins and sip some warm cider on a crisp fall day in a festive sweater coat, wool hat, and chestnut-colored high boots.

Stay fabulous,

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Sherita Rankins
Sherita Rankins

Detroit born, NYC based Model, Actress & Host, is the Editor-in-Chief of Busy Wife Busy Life. This fashion expert and former finance professional loves to travel and is a total foodie. When she is not staying “busy” she loves to cook, play tennis and relax on the beach.

Find me on: Web | Twitter | Instagram | Facebook

1 Comment

  1. September 19, 2019 / 12:47 am

    That was an interesting post. I really like your ideas. Thanks for sharing your fashion tips with us. You are looking so beautiful in this outfit. I love your fashion style. All the outfits are perfect for any occasion and can never go out of style. Thanks for the lovely post.

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