Got your first date? Time to find the perfect outfit that says confident, cool, and unforgettable! We’ve curated 35+ first date outfits, ranging from flirty midi dresses to smart-casual combos that scream “I’m interesting!”
Whether you’re grabbing coffee, hitting a trendy restaurant, or enjoying a casual hangout, these outfits are your secret weapon to making a killer first impression and landing that second date.
1. Co-ord Top and Skirt Set
Match your first date outfit with the spring floral aesthetics in this chic outfit! To keep up that laid-back energy, skip the accessorizing part and opt for contrasting stilettos!
2. Bustier Top and Side Split Skirt
Vintage-inspired first date looks never miss to deliver feminine energy! If you have a pink dress, pair metallic court heels and gold jewelry to pull off a statement look!
3. Floral Maxi Side Split Dress
Your go-to first date outfit for casual bar-like settings, these summer dresses balance out comfort and chicness with stiletto heels and charm jewelry!
4. Denim Jacket and Flare Dress
A neat jean jacket and flare dress combo is easily one of the most adorable first-date outfits you can opt for. With charm accessories and wedge heels, you’re set to impress on any summer day!
5. Pattern Shorts and Loose Fit Sweater
Movie first dates offer the perfect setting for something chic + cozy and this fit pulls off that aura naturally! Add in tan boots and a metal watch and you have an impressive outfit to don!
6. Loose Fit Sweater and Skinny Jeans
While skinny jeans have been a no-show in Gen-z fashion, this combo can still create a classy first date outfit to highlight your curves! All you need to tie the look together are some leather belts and stackable rings!
7. Cut Out Bodycon Dress
A body-hugging fit like this one is the perfect blend of sass and hotness for your first dinner date! Opt for bold colors with this one and stick to neutral-toned platform heels to nail this look!
8. Halter Neck Side Split Dress
In the mood for a dressy first-date ensemble? This all-black outfit has the perfect touch of sophistication when you pair it with mini gold hoop earrings and classic Louboutins/ solid court heels!
9. Denim Shirt and Pants
Rock a classic denim-on-denim combo for your first dates in summer and match it with neutral-toned heels and rhinestone stud earrings!
10. Velvet Bodycon Dress
With mesh tight to pair the dress in, these velvet first date outfits scream elegant night glam! Go subtle with the makeup and opt for a crescent bag to complete this outfit!
11. Puff Sleeved Floral Maxi Dress
Minimal and modest, these floral dresses capture that cottage core aesthetics for spring first dates! Add in a vintage watch and strappy heels to nail this look!
12. Blazer Dress
For an edgy first date look that he will remember, try on blazer dresses like these! Minimal pearl jewelry and embellished court heels are apt for balancing out the look!
13. Solid T-shirt and Rubbed Mini Skirt
Sometimes, a comfy and laid-back first date outfit is all you need to feel relaxed! Get creative with footwear and opt for ankle socks + court heels for that fun attitude!
14. Floral Strap Dress
Florals to match first dates in a cottage setting! Now, that’s as relaxed as you can get your outfit to be! With hoop earrings and neutral-toned heels, you add in a feminine appeal!
15. Long Sleeved Bodycon Dress and Leather Jacket
A leather jacket is all you need to layer your bodycon dresses with, for a confident first date look! With this one, try opting for minimal gold hoop earrings and wedge heels for a little sass!
16. Sweater, Tiered Dress and Cropped Jacket
Cozy wintertime first dates and a cozy feminine ensemble that ooze old money vibes! This outfit is apt for that when you pair the combo with stud earrings and tan boots!
17. Turtleneck Ribbed Top and Flare Dress
When you have a first date planned in an amusement park, Disney princess-inspired outfits are epic! This Cinderella-inspired look can be paired with silver pumps and a half-updo hairstyle!
18. Co-ord Set and Oversized Blazer
If you have a co-ord maxi skirt and top set, you can create a fancy first-date outfit by adding a contrasting blazer! Pearl accessories and stiletto heels are the only final touches you need!
19. Summer Crush Dress
For a soft summer glow on your first dates, try on stylish crush dresses like these! While they work well with practically any footwear, for a feminine touch, you can opt for open-toe heels!
20. Puff Sleeved Ruffle Dress
Fall-time first dates call for aesthetic and cozy dress-ups like these dark-toned ruffle dresses! For a hint of goth customization, opt for knee-high slouchy boots, fedora hats and stylish thread bracelets, in all black!
21. Fit and Flare Dress
Touch upon that fine balance between classy and relaxed on your first dates, with monochrome dresses like these! With a floppy hat and stiletto heels, you’re all set to impress!
22. Front Cut Out Long Sleeved Bodycon Dress
First date night in high end restaurants calls for romantic outfits and this bodycon dress creates just that. These dresses slay when paired with hoop earrings and platform heels!
23. Fit and Flare Ruffle Dress
Get creative with your summertime first date look with this unique dress! The ruffles pair well with buckle shoes and choker necklaces and you can always add a bow detail to your hairstyle!
24. One Shoulder Flare Dress
Why settle for lazy when you can have a flirty nighttime first date fit like this one! If your date setting has heavy lighting, try pairing the dress with shimmer purses and stiletto heels!
25. Animal Print Cami Top and High Waist Jeans
A casual combo like this one can also make for flattering first-date outfits when you pair the look with strappy heels and charm accessories!
26. Ruffle Sleeved Deep Neck Dress
Ice cream dates are always epic when you have a pastel/light-toned flare dress! Try sticking to minimal accessories with this one, except for stud earrings and a pair of solid pumps!
27. Cardigan, T-shirt and Plaid Skirt
Layering contrasting clothes for your first coffee date outfits is a cute way to show your creative side! With this one, try adding white sneakers and stud earrings for an elevated look!
28. Side Cut Out Ribbed Flare Dress
These ribbed dresses aren’t just comfy but exceedingly flirty when you pair them with stiletto heels and gold jewelry on your first dates. Throw in a straw bag for that hint of boho styling!
29. Halter Neck Button Down Dress
Vintage-style printed dresses like these in dresses always slay as refined first date looks! All you need to make the look polished are a pair of hoop earrings and some rocking wedge heels!
30. Long-Sleeved Bodycon Dress
Don a killer body-hugging outfit like this one on your nighttime first date for that hot appeal! With minimal gold accessories and platform heels, you have a confident look ready!
31. Bustier Dress
For first date outfits with a hint of a neat and preppy appeal, try a solid bustier dress with pearl jewelry! If your date is during the fall, you can layer this expensive look in mesh tights and longline coats!
32. Cropped Jacket, Straight Leg Jeans and Strap Top
Does your first date have an arcade-esque setting? Try on this 80s street fashion-inspired look with funky print sneakers to nail the aesthetics!
33. Cut Out Knot Front Bodycon Dress
Go monochrome on your first date with solid bodycon dresses like these for that effortless appeal! Hoop earrings and stiletto heels are great ways to style the dress!
34. Button-Down Strap Dress
First dates in a yacht call for light and airy fabric to ease in the comfort! With these button-down dresses and stiletto heels in black tones, you get that feel with a hint of elegance as well!
35. Strap Flare Dress and Knot Shirt
Go country-style on your first date picnics with this chic ensemble! Don’t shy away from throwing in straw hats, wedge heels, and charm accessories as they all blend right in!
