10+ Cute Outfits to Impress Your Boyfriend

Co-authored by Spencer Shimada and Hannah Madden

Last Updated: March 20, 2024 References

Picking out what to wear can be tough—but it’s even tougher when you have your boyfriend to think about! Choosing outfits is all about dressing for the occasion and making sure you’re comfortable (and looking super cute). We’ve compiled a range of casual, fancy, and formal outfit ideas you can use to impress your boyfriend and make him do a double take when you walk through the door.

1

Jeans and a T-shirt

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This is a classic look to wear when you’re just hanging out. If you two don’t have any real plans for the day, throw on some boot cut jeans and add your favorite T-shirt up top. Some sneakers and a few chain necklaces will pull this outfit together in no time.
- If this look feels a little plain for you, jazz it up by adding a crew neck or a puffer jacket.
- Put your phone, wallet, and keys into a fanny pack or a small backpack when you head out.
- Try styling yourself utilizing contrasting colors. For example, if you'll wear light colors on your top half, wear dark colors on your bottom half. ^{[1]
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  Spencer Shimada
  Image Consultant
  
  Expert Interview. 22 October 2021.}

2

Shorts and a band T-shirt

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It’s a cool and casual outfit that looks put together. Throw on your favorite pair of jean shorts, then add a band tee on top. Add some edge with a studded belt and throw on some comfortable sneakers to round out this look. ^{[2]
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- Accessorize with a bucket hat and a few rings to make your outfit pop.

3

Sweater and cropped pants

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Stay comfy and casual while looking put together. If you’re just hanging out with him and his friends, put on an oversized sweater and pair it with some capri-length pants. If the sweater has a pattern, match the color of your pants to a color in the sweater for a cohesive look.
- Throw your hair up into a messy bun or some French braids to keep the casual vibe going.
- Pair your outfit with flats or sneakers and a few flashy rings to top it all off.

4

Summer dress

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Show off your legs on a casual day out. If the weather is getting warm, grab a flowy summer dress out of your closet and pair it with some sandals. Add a thin necklace and a few bracelets for an easy outfit. He’ll be so entranced by the extra skin you’re showing off, he won’t know what to do with himself! ^{[3]
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- Summer dresses come in all shapes and styles. You can go for a pattern to stand out, or keep it simple with a bold yet solid color.
- Summer dresses are perfect for going out to lunch, picnicking in the park, or walking around your neighborhood.

5

Jumpsuit or romper

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This look is perfect for a casual lunch date. If you and your boo are hitting the town for mimosas or sandwiches, throw on your favorite one-piece jumpsuit or romper. Add a belt to define your waist a little more and put on some sneakers to complete your look. ^{[4]
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- Patterned jumpsuits really stand out, while solid-colored ones are a little more subtle.
- Pack your essentials into a small backpack to keep with you during the day.

6

Flowy midi dress

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This look is perfect for a date during the day. If you’re doing something that involves a lot of walking around (like going to the zoo or visiting a park), put on a midi dress that hits around mid-shin. Add a pair of comfy sandals and some long earrings to look cute and stay comfortable. ^{[5]
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- Draw attention to your legs by adding an anklet to your outfit.
- To go from day to night, simply swap your sandals for a pair of heels or knee high boots.

7

Skater skirt and heels

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Look dressy yet casual for date night. Put on a flowy A-line skater skirt, then pair it with tights and high heels. Add a flowy blouse up top and a statement necklace to look cute and sophisticated at the same time. ^{[6]
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- Sheer black tights go great with any outfit, while patterned ones can add a fun touch to a monochromatic look.
- Put your phone, wallet, and keys into a clutch or a small purse.

8

Trousers and a blouse

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This is a good outfit to meet the parents in. When you want to dress up just a little bit, pick out a pair of straight leg pants and wear them with a flowy blouse. Add some ballet flats or mules and a long trench coat to look put together without being overdressed. ^{[7]
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- This is also a good look for going out to dinner or heading to a work party.
- Pack your essentials into a small clutch and carry it with you throughout the night.

9

Crop top and a skirt

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It’s a cute date outfit for hitting the town. If you’re going out to dinner or dancing, put on a crop top that hits right at your waist. Pull on your favorite mini skirt and pair the look with some knee high boots for a bold finish that’s sure to impress your man. ^{[8]
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- If knee high boots aren’t really your thing, kitten heels work too!
- Accessorize with dangly earrings and a few necklaces.
- Pack your essentials into a crossbody bag to keep with you throughout the night.

10

Little black dress

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You’ll be all dressed up and ready to hit the town. Pull out a black bodycon dress and pair it with your favorite knee high boots or heels. If it’s chilly out, add a pair of sheer black tights to cover your legs while still looking put together. ^{[9]
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- Pair this outfit with a statement necklace, long earrings, and a pop of red lipstick.
- This is a great outfit idea for heading to a fancy restaurant or going to the theatre.

11

Monochromatic suit

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Turn heads at a work party or a more formal event. If you have somewhere fancy to go, try out a pant suit that’s all one color. Pink, red, blue, and green are all solid color choices that look good on anyone. Pair your look with black or brown dress shoes before you head out. ^{[10]
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- If your suit doesn’t have pockets, throw your essentials into a small clutch.
- You could also pair your pant suit with a pair of high heels.

12

Turtleneck dress

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Dress up on chilly days with a cozy look. Put on a turtleneck dress that hits around mid-shin. Pair it with some sheer black tights and a pair of heeled booties to put your outfit together. If you’re still a little cold, throw on a long trench coat. ^{[11]
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- Add a statement necklace and a few bracelets to top this look off.

13

Formal gown or suit

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Black tie events call for extra glam. If you have somewhere really fancy to go, pick out a floor length gown or your best suit and bow tie. Put on some subtle makeup and wear your hair up for the perfect glam look that’s sure to impress your man.
- Pair your outfit with dress shoes or heels for the perfect look.
- Carry a small clutch to keep all your essentials.
- Don’t forget the jewelry! Thin necklaces and small bracelets are the perfect addition to any fancy outfit.

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Tips

Confidence radiates through your body language, and if you walk with your head held high and your shoulder back, a boy is sure to notice. ^{[12]
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Spencer Shimada
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Expert Interview. 22 October 2021.}

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If you’d like to infuse some color, start off with an accessory such as a colorful bracelet, earring, or interesting necklace. ^{[13]
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Spencer Shimada
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Expert Interview. 22 October 2021.}

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If you aren’t sure what to wear, ask him what he’s wearing. You can gauge how formal something is by the outfit he picks.

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10+ Cute Outfits to Impress Your Boyfriend

Steps

Jeans and a T-shirt

Shorts and a band T-shirt

Sweater and cropped pants

Summer dress

Jumpsuit or romper

Flowy midi dress

Skater skirt and heels

Trousers and a blouse

Crop top and a skirt

Little black dress

Monochromatic suit

Turtleneck dress

Formal gown or suit

Expert Q&A

Tips

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