Four Chic Fall Date Outfit Ideas.

I’m always getting asked for outfit ideas for dates! A few years back, we had Emily Holmes Hahn (founder of white glove matchmaking service LastFirst) on the blog to share some ideas on date night outfits. Today I wanted to update that post with new options + some fresh ideas for a Fall date! I do want to also share two of my dating essentials: silky camisoles from Cami New York (the best + they layer so well under little jackets) and Sarah Flint‘s heels. Any of her 85mm heels are perfect for dates. They’re sexy and make your legs look amazing BUT they are also very comfortable so you’ll feel your best and be able to travel should your date move from drinks to dinner or to another bar! (I do the 85mm Perfect Pump or Perfect Sandal).

Also relevant: 10 cute tops that are perfect for date night, and even more date outfit ideas!

Fall Date Night Outfits

date night outfits

This is pretty much my go-to look for a date. Simple easy pieces that are comfortable but still sexy. I love a little leather (or faux) jacket with a slinky camisole. I also wanted to share this affordable silky cami (in plus sizes here!)

Downtown Dinner or Drinks Date:

BlankNYC Moto Jacket // Cami NYC Camisole // Madewell Jeans // Sarah Flint Perfect Pump (take $50 off your first pair with code GRACE50) // Gorjana Necklace // Madewell Earrings // Clare V Clutch

winter date night outfits

For an uptown dinner date/a fancier evening out, I love a monochromatic look. This sexy little dress would ordinarily be a LOT with the over the knee boots but the tuxedo jacket tones things down a little bit. LOVE this look.

Uptown Dinner Date:

Topshop Satin Minidress // H&M Tuxedo Jacket // Jessica Simpson Boots // Tory Burch Leather Bag // Mango Hoop Earrings

casual date outfit ideas

Got a more casual date? I love something like this. Simple jeans and a fitted sweater, with interesting accessories that show you have a personality!

Casual Fall Date:

Topshop Jeans // Leith Sweater // Loeffler Randall Zebra Bag // Topshop Coat // Sarah Flint Perfect Pump (take $50 off your first pair with code GRACE50) // Alison Lou Hoop Earrings

fancy date outfit ideas

For a fancier dinner or an office party, I love a metallic mini dress, fun earrings, and leg-lengthening nude sandals. Add the tuxedo jacket (same jacket from the uptown dinner date) to pull it all together!

Fancy/Party Date:

H&M Tuxedo Jacket // Jennifer Behr Earrings // All in Favor Metallic Dress // Sarah Flint Perfect Sandal (take $50 off your first pair with code GRACE50) // Gucci Leather Wallet


Leave a Comment

Leave a Comment


  1. C:

    The first three looks are great! But I would never recommend the 4th for a corporate holiday party – way too much skin! A blazer would make it a little more appropriate, but I think at most workplaces, you really do want to err on the conservative side, particularly as someone’s date.

    12.9.16 Reply
    • graceatwood:

      I would agree with you! I tend to dress a little bit more conservatively and would personally most definitely add a blazer and make sure the tights are really opaque. That being said I think it probably depends on the company.

      12.9.16 Reply
    • Totally agree too, depending on the company! The Elizabeth and James blazer in the second look is so versatile, it would be perfect with this outfit! xEHH

      12.9.16 Reply
  2. dang, these are pretty hot looks!
    i love that red dress.

    xo, brittany
    i’ve got pretty wishlists for mama & babe on my blog today

    12.9.16 Reply
    • graceatwood:

      I know, me too – it’s so pretty!!! Thanks for stopping by, Brittany – have a great weekend! xo

      12.9.16 Reply
  3. Love your suggestions! These would be great outfits on a glam night out! ❤️✨

    Charmaine Ng | Architecture & Lifestyle Blog

    10.15.19 Reply
  4. Andrea:

    Love all these looks! I always wear the same standard jeans and a cute top so its helpful to see some variety!

    10.15.19 Reply
    • Agreed, even writing this post helped me get out of my standard cute top/jeans routine!!!

      10.15.19 Reply
  5. Elizabeth:

    This is perfect timing! I have two dates this week!!! (after a long dry spell haha) and I’m in need of outfit inspo. Still a little warm here in New Orleans but supposed to get a cold front this weekend – if either of these lead to a second date I’ll definitely be pulling out my leather jacket to pair with a camisole.

    P.S. loved the latest Bad on Politics episode – will be super helpful when watching the debate tonight!

    10.15.19 Reply
  6. Brittany:

    Really loving all the looks. Look 2 is way outside my comfort zone but 100% agree with the tuxedo jacket…it makes it less scary!! Love them all! Thank you for sharing!

    10.15.19 Reply
  7. These are great outfit ideas!! Love the second look!

    10.16.19 Reply
  8. Gorgeous looks. Thanks for sharing!

    10.16.19 Reply
  9. Lia:

    Yes! This is all so great! I have been waiting to get a date night with my hubby for so long since having a baby. But these outfits are great!

    7.27.20 Reply