Outfits Under $100: 3 Stylish Looks for First Dates
With the start of a new school year comes a new crop of people to meet, and inevitably, some first dates. Dressing for a first date can be tricky: you want to impress your suitor, but you don’t want to overdo it or feel uncomfortable, and that predicament can lead to many frustrating hours in your closet.
But fret no more – I’m here to solve your date wardrobe dilemma, without busting your budget. Here are some cute and inexpensive outfits for common types of first dates, along with some dos and don’ts:
First Date Fashion Dos and Don’ts
- DO wear something that makes you feel beautiful and confident, like your favorite shirt or your “good luck” bracelet.
- DON’T try out a new look or wear something you wouldn’t normally wear. You’ll fidget, worry too much about how you look, and feel uncomfortable. Comfort is key.
- DO accentuate your natural beauty with figure-flattering shapes and natural-looking makeup.
- DO dress appropriately for the activity. Taking a hike together? Don’t wear heels.
- DON’T wear anything too revealing or too tight — save the clubwear for the club. Trust me on this: It’s always best to keep your wardrobe classy and comfortable on a first date, especially if you want a second date with this person.
- DO make eye contact and SMILE. No matter what you wear, a smile will always be your best accessory.
Outfit #1: Coffee & Conversation
Product Info: Sweater Dress, Necklace, Bracelet, Boots, Tights
A comfy and cute sweater dress is both fitting for fall weather and flirty for a first date. When you’re just having coffee and getting to know each other, there’s few limitations on what you can wear: It’s not as if you’re playing softball or riding bikes; you’re just sitting, so you can wear a skirt without worrying about it being inappropriate or uncomfortable.
Another bonus? Wearing a dress gives your new guy or gal a glimpse of your gams, but while wearing tights, you’re still not revealing too much. Keep it casual with flat footwear, like these versatile boots.
Outfit #2: Picnic in the Park
Product Info: Cardigan, T-Shirt, Beret, Skinny Jeans, Ballet Flats
Picnics are a classic choice for romantic first dates, and they’re extra-special in the fall when we’re enjoying the last doses of beautiful weather before the winter chill sets in.
As far as picnic attire goes, it’s a good idea to wear pants since you’ll be sitting on the ground: You won’t have to fret about having a Britney/Paris/Lindsay moment, and you’ll be warm. And don’t be afraid to show a little personality by sporting your favorite band tee. It’s a great conversation piece! Finally, bring along a sweater in case of a cold front.
Outfit #3: Movie Night
Product Info: Top, Blazer, Jeggings, Heels
Unlike coffee or a picnic dates, in this scenario you’ll be hitting up a movie at night — so pump up your day look a notch so it’s a little sexier and dressier.
A pop of color, like this hot pink top, gets your date’s attention without looking tarty. Also, movie theaters tend to get cold, so bring along a blazer. And it may seem high-maintenance for some, but movies are a great time to wear heels! Why? Because you get to sit down for most of the night!
What do you think?
Have any first dates coming up? What do you like to wear on dates? Have you been seeing your guy or girl for a long time? Do you still have date nights in long-term relationships, and do you still dress up for them? What did you think of these outfits? I’d love to hear from you! Please leave a comment.
Posted on on October 19, 2010 / Filed Under: Shopping / Tags: Budget Fashion, Budget-Friendly, Dating, Featured, first date, Outfits Under $100, Shopping
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Irina
this is why i love these looks. I wish I still went on dates so I could dress up. Picking out date outfits is so much fun! But my boyfriend and I have been dating for 8 months, and it has been long distance for two months :/ So I don’t really get to do this anymore.
Kylie
ali – great job! all of these outfits are super gorge (the first one is my personal fave – i would wear it for an everyday outfit too)!
xoxo, kylie
Milana
I love the third outfit. I would definitely wear it!
CG
omg, all those outfits look super comfortable.. my ‘bf’ did hint at heels being a nice look and i scoffed with a “ugh, but they’re my feet!!!”.. but heels on movie night are definitely doable! thanks for the tips!
cici
I love this post, all of the outfits are cute are really affordable. The first ones my favorite
Crystal
my guy and i have been together almost 5 years and i rarely “dressed up” for him on scheduled date nights, but now it seems like we’re in a rut. maybe dressing up for him would be a great way to break out of it. thanks for the great ideas! love the outfits.
Ashley - Flagler College
Love that first outfit!
Britney
i have the yellow beret. <3 it. the color isn't that bright though..but i like it better this way. and love the post!
s.
i dont know if i would wear heels to the movies… might give the guy the wrong impression (too high maintenance??) to dinner yes, but movies are casual to me..
Jay, Common Sense and Stilettos
These are all really cute! :)
Valeria
I love this outfits, they’re so chic and they look comfy.
Although I have to say that I’d like to see something besides dresses,skirts, legging and skiny jeans, since some of us don’t have good legs to go around in those things =/
Colleen
I just want to thank you for saying “Wearing a dress gives your new guy or gal a glimpse of your gams”. I’m sure that little add-in made any lesbian or bi readers smile. Thanks :)
Mandi
ughh those shoes in the first outfit are adorable, and the dress too. actually might look into buying. thanks.
Sari
So great! I think these outfits are great for any occasion, and I can probably re-create most of the looks from stuff I already own- awesome! And I love the yellow beret in outfit #2, it’s a nice pop of color. Yay! Too bad I won’t be going on any first dates for awhile.
M
@Colleen: you’re right, that is cute :) But I’m a lesbian (I’ve been with my girlfriend for two years) and I didn’t even notice until you pointed it out! It’s nice that people are so much more inclusive now.
Lauren Hooker
It’s winter again! Could you do a post on cute coats for 2010? :)
Brenda
I agree with s. would not wear heels to the movies. dress comfy for watching a movie!
Ali - University of Missouri
@ Irina – I know long-distance relationships are rough, but you can always dress up for a night out with your girls, too!
@ Kylie – Thanks! I think these work for everyday outfits, too. And that’s how a first date outfit should be in my opinion — you should wear something that’s “you,” something you normally would wear. If you try too hard and dress too far out of your comfortable zone, you’ll free uncomfortable and not like yourself all night.
@ CG – That’s so cute that your bf “hinted” to wear heels. I read recently that according to a new study, guys don’t even notice when you wear heels. WRONG! My boyfriend always notices, and guys find the extra height and confidence sexy and alluring.
@ Crystal – 5 years, wow! Congrats. I know how you feel (at least to a degree) because I’ve been with my guy for 2.5 years (a lifetime in college!) Being in a long-term relationship, I am a HUGE advocate for date nights! You need to have special nights out together to keep the butterflies fluttering in your stomach. Even if you live together, it’s important to take time getting ready separately, making an effort to look nice and feel confident, and then going out on a date that’s a bit more special than your usual nights. 2.5 years later, I still get butterflies while primping and waiting for my boyfriend to pick me up. That’s essential for long-term romance.
@ s. – Yes, heels could give the impression you’re high maintenance OR it could just give the impression you care about looking nice for your date. Heels are nice for a movie night because you get to sit the whole time, so it’s painless! Heels are good for dinner dates, too.
@ Valeria – I know how you feel because my legs aren’t my favorite attribute BUT wearing slim-fitting jeans or leggings is actually more flattering than wearing a looser fit if you have thicker legs; trouser jeans or flares actually make you look bigger. To feel more comfortable wearing skirts and dresses, you could try wearing opaque tights under them, which slims legs. If you really hate skinny jeans, just swap them out in these outfits and wear bootcut jeans instead.
@ Colleen – I’m glad you noticed and appreciated my language :)
@ Brenda – At your a movie, you’re sitting the whole time, which is why it’s a good time to get away with heels – you won’t be uncomfortable! I don’t think anyone should dress too comfy on a first date, regardless of the activity. If you don’t make an effort on the first date, you never will!
Thanks everyone for commenting!! I love reading all your comments and appreciate every piece of feedback!
Audrey C.
These are all so cute! I’m not going on a first date anytime soon, but I will definitely be imitating the first outfit for coffee with my bf!
I also like that you added a blazer for the movie look—people always forget, but it gets COLD in there!
Erin
I’m going on my first date (ever) soon so I will SO use this info!
These outfits are so cute! #2′s my fave!
liss
i looove the balzer!! so cool
i dont have one though, i just dont know what to wear with it :(
liss
sorry i meant blazer
and Erin: number two is my favourite too. i luv it