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).
Fall 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:
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:
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:
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!