Getting ready for a date with your boyfriend can be nerve-wracking just try to remember that we’re all human and nobody is perfect! Failing to do so can be embarrassing for the two of you or for those who happen to witness the event.
Sure, there are some dos and don’ts when it comes to first dates, but the only person you should be trying to impress is your date. Avoid looking like you’re trying too hard by picking something casual and comfortable there’s no need to wear your best dress or show too much skin.
Now that you’re ready to go, here are a few outfits for your first dates.
Table of Contents
- 1. BLAZER + CURVE-HUGGING MIDI
- 2. SILK DOT-PRINT DRESS
- 3. STATEMENT BLOUSE + JEANS
- 4. LEATHER JACKET + TANK TOP
- 5. CLASSIC DRESS + JEANS
- 6. FLORAL DRESS
- 7. HIGH-WAISTED SKIRT
- 8. FLOUNCY DRESS
- 9. LIGHT SWEATER DRESS
- 10. MAXI DRESS + SKINNY JEANS
- 11. POLKA DOT TOP
- 12.STRIPED TANK TOP
- 13. CROP-TOP+ HIGH-WAISTED JEANS
- 14. FLORAL PUFF SLEEVE BELTED DRESS
- 15. CROP TOP + HIGH WAIST PENCIL SKIRT
- 16.CAP SLEEVE BLOUSE
- 17. SLOUCHY BLAZER + SKINNY JEANS
- 18. LITTLE BLACK DRESS
- 19. BLOUSE + STRAIGHT-LEG TROUSERS + FLATS
- 20. V-NECK CROPPED TOP + HIGH WAIST SKIRT
- 21. SWEATER +LEGGINGS + BOOTS
- 22. VINTAGE DRESS + COMFY BOOTS
- 23. PLEATED DRESS
- 24. JUMPSUIT
- 25. MIDI SKIRT
- 26. MIDI DRESS
- 27. SHOULDER A-LINE DRESS
1. BLAZER + CURVE-HUGGING MIDI
This is a simple yet chic outfit that goes great with a simple clutch and pump. Two key attributes of this outfit is that it makes her look like she cares but still allows her to be playful and move around freely while also looking sophisticated, chic, and put together. This is perfect for women who want to feel classy but still want to be able to have fun and enjoy their day or night out with their significant other.
2. SILK DOT-PRINT DRESS
This is an elegant outfit for a first date. First dates usually include going to lunch, dinner or a movie so this outfit is perfect if you want her to feel comfortable in her athleticism. This dress is comfortable enough for her to sit cross-legged, stand up and walk around all night. The headband compliments the dress and makes it more personalized which makes it easier for her to feel confident that she looks good and like herself when she sees herself in the mirror at home.
3. STATEMENT BLOUSE + JEANS
For your first date, keep things casual in jeans and a statement blouse. Tie up the blouse just enough to show off the belt and heels. Top it off with a trendy headband for an effortlessly chic look.
4. LEATHER JACKET + TANK TOP
For your first date, wear an oversized clutch and rock a perforated leather jacket over a tank top and pair it with a simple necklace or pendant instead of focusing on your outfit too much.
5. CLASSIC DRESS + JEANS
If your date is a bit more formal, wear a classic dress for an effortless yet chic look. Accessorize with jeans and low-heeled pumps for a more casual look.
6. FLORAL DRESS
If you’re trying to keep things casual and comfortable on your first date, this is your best bet! A floral dress paired with brown leather boots will make you look amazing without making you uncomfortable.
7. HIGH-WAISTED SKIRT
Wearing high-waisted skirts like in the picture is the perfect way to display your curves without overdoing it on your first date with him. Top off your look with white sneakers over basic tees.
8. FLOUNCY DRESS
A flouncy dress is the perfect outfit when you’re on a first date with your boyfriend. Pair a soft clutch and heels over your dress for an effortlessly-chic look. A flouncy dress and some great boots will show off both your gorgeous outfit AND your amazing legs. This look is also good because you can show a bit of skin, but not too much.
9. LIGHT SWEATER DRESS
Avoid wearing heavy clothes when you’re on a first date. Wear a light sweater dress and pair it with a long coat and supportive boots for an effortlessly chic look.
10. MAXI DRESS + SKINNY JEANS
For your first date, rock some booties and a maxi dress for an effortlessly chic look. A simple headband is perfect for easy styling and pairing it with ripped jeans will give you a more casual look.
11. POLKA DOT TOP
This cute top and pair of booties are perfect for a spring date. You can wear them with flats — but if it’s really cold out, consider wearing some nicer heels or boots that go up to your calves.
12.STRIPED TANK TOP
For your first date, wear a long-sleeve cardigan and pair it with skinny jeans for a more casual look. Pair your outfit with high-heel pumps for a more sophisticated vibe and finish off the look with fresh makeup.
13. CROP-TOP+ HIGH-WAISTED JEANS
Wearing high-waisted jeans like in the picture is the perfect way to display your curves without overdoing it on your first date with him. Rock some booties for an effortlessly chic look.
14. FLORAL PUFF SLEEVE BELTED DRESS
This outfit is perfect for women that want to look cute and femenine but still be able to walk and keep up with their date. The dress compliments the ankle boots which are practical for a night out with enough heels to wear all night. This outfit is perfect for summer or fall dates.
15. CROP TOP + HIGH WAIST PENCIL SKIRT
This outfit is perfect for casual dates. The idea behind this outfit is to look cute but still be able to walk in. This can be worn in all seasons and is perfect for women who are going out for a night on the town or a casual dinner.
16.CAP SLEEVE BLOUSE
This outfit compliments the ankle booties from the other outfits and goes perfectly with them without being too much of an interruption to the outfits choice of simplicity. This can also be worn in all seasons depending on whether or not you choose darker colors of accessories on top, however, if you do choose this combination it will compliment fall clothes as well as spring clothes.
17. SLOUCHY BLAZER + SKINNY JEANS
This outfit could be easily worn during the day or night depending on how you accessorize it. For example, this outfit could be semi-casual with sneakers or dressed up with high heels. The idea behind this outfit is to look sleek and put together while still being comfortable enough to walk around all night. This is perfect for women who are going out for a casual dinner or staying in to watch movies with a special someone.
18. LITTLE BLACK DRESS
This is a great outfit if you’re trying to flirt a bit! A little black dress and a vest will make your legs look amazing, and since you’re wearing flats, you can avoid the awkward heels-on-the-date experience. This look is also perfect for winter weather because of the vest!
19. BLOUSE + STRAIGHT-LEG TROUSERS + FLATS
If you’re the girl who wears flats to every occasion, this is the perfect outfit for you. A comfortable blouse and some straight-leg pants can be worn with your beloved flats, and even though it may look a little “lady-like,” you’ll still be able to flirt as much as your heart desires.
20. V-NECK CROPPED TOP + HIGH WAIST SKIRT
This outfit is perfect for the first date. The outfit is simple, relaxed and slimming which are the attributes that a girl wants to feel when stepping out on a first date. The only thing that could improve this outfit is if she wore something underneath but it really doesn’t need it because this is not going to be a night on the town with grown ups. This also goes well with casual shoes like flats or sneakers so women can still look classy without worrying about looking uncomfortable in their choice of footwear.
21. SWEATER +LEGGINGS + BOOTS
Leggings have been out for quite some time, but they’ve yet to lose their popularity! A legging/sweater combo with boots is trendy enough to wear on your date and is comfortable enough to keep you happy throughout.
22. VINTAGE DRESS + COMFY BOOTS
This look will work if you don’t care too much about your makeup or if it’s winter! A vintage dress and some comfy boots is not only comfortable, but it will also help to take away any awkward vibe (because why else would you be wearing that dress?).
23. PLEATED DRESS
If you don’t want to spend too much time on your first date appearance, this is the perfect look for you. A pleated dress makes your legs look amazing and is also very flattering — but of course, don’t forget to wear some cute sandals instead of heels unless it’s winter.
The idea behind this outfit is to wear something that is exciting, glamorous and feminine without feeling like you are going on a hunt for someone. The jumpsuit compliments the heels, bag and makes her feel like a million bucks even though she is wearing flats. This goes well with casual shoes or wedges for women who aren’t too worried about how comfortable their shoes are as long as they look good with the outfit.
25. MIDI SKIRT
If you have trouble choosing what to wear, this is a great outfit to try. A midi skirt and a pair of heels will dress you up without feeling too uncomfortable. You can also add some glamor to the outfit by carrying around a small bag.
26. MIDI DRESS
If you’re having trouble deciding what to wear, this is a great outfit to try. A midi dress paired with flats and some nice earrings or a necklace will add some glamor to the outfit. You’ll still be comfortable, but you’ll feel a little bit more stylish.
27. SHOULDER A-LINE DRESS
A-line dress is trendy and stylish but also simple enough for casual first dates. The simple color choices make it easy on the eye and the shoes are easy to move around in. This can be worn in all seasons depending on the fabrics chosen although, it would look best during warmer months so that your legs can show through the skirt of the dress. Add some jewelry to make the outfit more glamorous.
There are several ways to dress for a first date with a boyfriend. Wear clothes that you normally would wear on a first date. Try not to wear something that’s too revealing or too feminine. That will make him uncomfortable and he will probably be disappointed.Take into account his personality as well.