What Should You Wear When You Visit Your Boyfriend?

Written by Abby Rosenblum | Edited by Kira Jan

Last Updated: May 28, 2022 References

Throwing on a cute outfit to go hang out with your boyfriend can feel like a bit of a balancing act. On one hand, you want to look really good, but at the same time, you want to play it cool and not look like you’re trying too hard. How do you strike the balance between cute, comfy, and totally you? We’ll help you get ready with this quick list of outfits that’ll make you feel amazing and make your boyfriend go “woah” the second you walk through the door.

This article is based on an interview with our matchmaker, Abby Rosenblum, founder of The Social: Modern Matchmaking. Check out the full interview here.

1

Jeans and a cute top

Pick a casual outfit that makes you feel comfortable. Go for clothes you’ve worn before, since wearing something totally new might leave you stressing about how it looks and feels.^{[1]
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Expert Source

Abby Rosenblum
Matchmaker
Expert Interview. 20 October 2021.} For instance, when it comes to picking a shirt, stick with a neckline that you’d wear every day. If you’re a fan of tank tops, for example, try a snug tank top and light-wash distressed denim with faux-leather sneakers for an effortlessly cool look. As a general rule, balance out your silhouette by pairing a tighter top with looser jeans or an oversized top with fitted bottoms.
- Slide into skinny jeans and a cropped hoodie if you want to show a little more skin.
- Pair straight-leg jeans with your favorite graphic tee for a slightly edgier, androgynous look.
- Heading over after dark? Try your favorite jeans with a silk cami or top with a bit of lace detail to add romance.
- Wear darker denim without any rips and a slightly more conservative blouse if you’re going to meet his parents.

2

Leggings and athleisure

Show off your lower body and stay cozy with this option. You can dress up or dress down workout and loungewear like sweatpants for a look that either feels chill or athletic. Feeling sporty? Pair your leggings with a workout crop top. If the wear turns a little colder, throw on a chunky knit sweater or hoodie with your trusty leggings. The key is to stick with tried-and-true clothes that make you feel great.^{[2]
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Expert Source

Abby Rosenblum
Matchmaker
Expert Interview. 20 October 2021.}
- To look super trendy, go for a monochrome set of leggings and a matching top with white sneakers.
- Dress up your leggings for an evening out with a metallic-colored bomber jacket and leather ankle booties.
- Tie up a tee shirt and throw your hair into a messy bun for a chill night at your guy’s house. If you’re staying in, don’t stress about your shoes—opt for fuzzy socks!
- You can even show up in sweatpants if that’s what makes you feel most comfortable.^{[3]
  X
  Expert Source
  
  Abby Rosenblum
  Matchmaker
  Expert Interview. 20 October 2021.}

3

His favorite tee or hoodie with your favorite pants

When you get the dreaded “I have nothing to wear” feeling, steal one of your BF’s outfits. Guys think it’s adorable when you can rock their favorite tee shirt, hoodie, or jersey.^{[4]
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Research source} All you have to do is add your favorite denim or leggings on the bottom. Go for a slightly fitted look to balance out an oversized shirt, and voila! You’ve got a boyfriend-approved outfit in just two minutes. After all, if he loves wearing that shirt or hoodie, he’ll probably like it even more on you.
- Tuck in the shirt and belt it with jeans if you want a more tailored look. Add ankle boots if you want to add sophistication.
- Own the oversized look by pairing the borrowed shirt with leggings and athletic shoes for a “just woke up like this” vibe.
- Got messy hair? No worries, play up the cute boyish look of this outfit by tossing on a baseball cap.

4

An off-the-shoulder top and shorts

Set a romantic mood and show off your neckline with this look. An off-the-shoulder top balances showing off some skin with leaving a little up to your boyfriend’s imagination. If you’re feeling bohemian, pick a flowy, puff-sleeve top that drapes off your shoulders. For a slightly sexier look, pick a ribbed cotton material that clings to your body.^{[5]
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- Opt for a white or pastel off-the-shoulder top paired with denim shorts and espadrilles (rope-soled shoes) for an outfit that’s perfect for a summer evening date.
- Throw on high-waisted shorts with a cute print and a black strapless top for a vintage look that’s a mix of “music festival” and “date night.”
- If you’re not into strapless bras, throw on a cute lacy bralette and let the straps show.

5

A pretty sundress

Sundresses give off free-spirited “girl-next-door” energy. Choose a flowy sundress for a simple outfit in the warmer months.^{[6]
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Research source} You can dress your outfit up with cute heels for the evening, or wear strappy sandals if you’re just headed over to your boyfriend’s house to hang out. Whether you want to pick a feminine floral pattern or stick to neutral colors with edgier accessories is up to you—wear clothes that make you feel confident.^{[7]
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Expert Source

Abby Rosenblum
Matchmaker
Expert Interview. 20 October 2021.}
- Style your sundress with sneakers and a denim jacket for the perfect daytime outfit to hang with your BF.
- Throw on a less-revealing sundress and platform wedge sandals if you’re going to visit your boyfriend and his parents.
- Balance out the romance of a sundress with practicality by adding a canvas chore coat (a boxy, menswear-inspired jacket) or shirt jacket on top.

6

A bodycon dress

Opt for a simple fitted dress if you’re looking to spice things up. If you’re comfortable in tighter clothing, you can’t go wrong with a bodycon dress. First of all, a bodycon shows off your figure and will leave your guy drooling. Second of all, as long as you pick a bodycon dress made from a soft cotton or jersey fabric, it’ll fit like a cozy second skin. Who says you can’t look sexy and be totally comfy at the same time?^{[8]
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Research source} Check out these outfits below, and pick whichever one makes you feel the most like yourself.^{[9]
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Expert Source

Abby Rosenblum
Matchmaker
Expert Interview. 20 October 2021.}
- Pair a black bodycon dress with a denim jacket and high tops for a chic, cool-girl look.
- Put an olive anorak jacket over a bodycon and wear lace-up boots for a casual outfit.
- Dial up the glam factor with a leather jacket, chunky accessories, and bright heels if you’re going out with your boyfriend.

7

A shorter skirt and sweater or tee

Try an above-the-knee pencil, skater, or a-line skirt for a sassier outfit. To turn a short skirt into a lounge-ready outfit for a night in with your boyfriend, pop on a hoodie or sweater. If you’ll be going somewhere nice to visit him, make your outfit classy with a v-neck blouse and a pair of nude heels.^{[10]
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Research source}
- Pair a plain white tee with a denim pencil skirt and sneakers for a super basic yet classic outfit.
- Tuck a baggy tee-shirt into a pleated skater skirt for a laidback look.
- For a 2000s-inspired grunge look, pair a plaid skirt with a graphic tee from your favorite band, lace-up combat boots, and a camo jacket.

8

A red shirt or red accessories with black accents

Studies show that men find red really attractive. If you’re looking to get extra attention from your boyfriend, skip the neutral shades and add a little of this passionate color. Try going for a red shirt or red dress with a black leather jacket for a mysterious, powerful look. If you don’t have any of those pieces, no worries. Try accessorizing a little black dress with red for classy elegance.^{[11]
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- Take a page from pop star style and go for red lipstick.
- Put on a red scarf for the chillier months.
- Try a red lace bralette for a seductive look.

9

Your favorite lingerie

Pick lingerie that makes you feel confident. Just remember you don’t have to change up your underwear drastically or wear anything that makes you uncomfortable.^{[12]
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Expert Source

Abby Rosenblum
Matchmaker
Expert Interview. 20 October 2021.} You might feel awesome in a matching set of black lacy underwear, or you might feel super hot in a sports bra that shows off your athletic side.
- Choose materials like silk and lace to create a seductive atmosphere.

10

Simple jewelry

Go for pared-down accessories that won’t detract from your features. Stick to accessorizing one main area. For instance, if you go for a bold necklace, ditch the bracelets. If you put on your flashiest earrings, go for a simple, delicate necklace. Not sure what jewelry to wear? Try picking something with personal significance.^{[13]
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Research source} The necklace your boyfriend gave you, the friendship bracelet you’ve had since first grade, or the charm you bought on your family vacation can be a great conversation starter.

11

Your signature makeup look

Stay true to your everyday style when it comes to makeup. If you’re the queen of winged eyeliner, more power to you. If you can’t tell bronzer from highlighter, and you opt for a natural makeup-free look, that’s fine, too. Studies and polls can’t say for sure whether men actually like less makeup or more makeup.^{[14]
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Research source} Do what feels comfortable and right for you!
- Go for a natural look with light-coverage BB or CC cream (which has more coverage than BB cream) instead of foundation. Then, add a little mascara and blush.
- For a date-night look, try out dramatic eyeshadow, cat-eye eyeliner, and bold lipstick. Or go for a red-carpet-ready smokey eye look.
- When you feel comfortable and confident with your look, you’ll be able to focus on having a good time!^{[15]
  X
  Expert Source
  
  Abby Rosenblum
  Matchmaker
  Expert Interview. 20 October 2021.}