Which fall outfit would you wear on a date?
Picture this: Your handsome crush asked you out to dinner on a beautiful fall evening. He picked out a neighborhood Italian restaurant, and you have butterflies in your stomach. He just texted, "I can't wait." Now, the big question is: What will you wear?!
Above, a cozy knit sweater with flattering jeans.
A chic belted dress.
A feminine silk dress with tiny flowers.
A simple yet sexy henley top. (I actually wore a shirt just like this on my first date with Alex.)
A 1970's-inspired red dress.
Which of these pretty outfits would you wear on a first date? Which suits your personality best? (I'd LOVE to get the sweater and dresses for the fall!)
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245 comments:
1 – 200 of 245 Newer› Newest»i'd go with the belted dress--it looks like the perfect mix between dressy and casual, which is good if you don't know how he will be dressed!
im the silk dress girl. I'm petite, so the pant/sweater combo makes me look weird. I look best in an above the knee dress with cute boots.
I would go with the first one for sure. Its always a good idea to wear something comfy but pretty on the first date. Love that sweater and her hair like that!
Definitely the sweater/jeans combo. I'm a total sucker for sweaters.
This gave me fleeting butterflies, what a fun scenario! I would pick the brown belted dress with a cardigan, so cute.
I like the silk on. the sweater is lovely too. if the restaurant had outdoor seating I would pick that.
I love the first outfit... the chic dorky glasses are irresistible and my husband love my black pair from Warby Parker.
Best Wishes!
Kelly
Mod Human Vintage
www.modhumanvintage.com
These looks are great. I would pick the chic belted dress with my favorite boots.
I remember those first dates with my now-husband. Oh, the butterflies! He was *always* so prompt. If he said, I'll pick you up in 20 minutes - it would be 20 minutes on the dot! I would be flying around the house, racing to get ready on time, ha. xo.
They're all cute - but 1 and 5 are most my style!
Either the silk or belted dress with flats to keep it low key.
The first or last outfit :)
I would wear all of them - just want my cute crush to ask me out : )
the silk or belted dress both are just screaming my name!
probably the silk dress with some flats. pretty but casual. :)
It would depend on the activity I would be doing on the date, but would probably go with the chic simple belted dress.
Much love,
B
I'd probably go with the red dress.
silk dress with tiny flower is gorgeous!
the silk dress with flowers is my fav!
I'm dying over that orange sweater and red dress. 100% cotton and in my price range! Sold!
I love that you remember what you wore on your first date. I just asked my husband if he remembered what he wore and not only did he remember his outfit, he remembered mine too. Sweetheart! I must have married the right man! I'm with Beth, belted dress all the way!
I love the last dress with boots, but I would want to go a little more girlie on a first date, so feminine silk dress with tiny flowers it is!
I'm all about jeans and a sweater - maybe with a cute pair of boots too if it were chilly. As an aside - I just bought the EmersonMade jeans and positively LOVE them. They're super comfy AND flattering. I highly recommend!
Becca
"1 or #2 Belted dress (minus the boots) - thanks for this, love all of these : )
the henley or the dress after. I like them all but I wouldn't wear #1 for a date. I like to show LEG!
haha, good point, HiLLjO!
nicole, that's hilarious -- always good to have someone be at least five minutes late, we ladies need some primping time! :)
Well I love them all.
But as far as what I'd want to be in so I'm comfortable in my own skin for date one,I'd have to say numero uno. Then I'd branch out into others.
the last one, definetly! but i think i'd add a belt, and wear my hair in a pretty braid :)
#2, I think :)
A flirty dress with little flowers! Guys go gaga over those.
the chic belted dress - only I'd tie in a fall cardigan. LOVE IT!
I love all the outfits! I'd probably ended up wearing the dresses because they are comfortable and feminine.
Bottom. But more accessorized.
And loving the new feel around here. Like a fresh new mani color or something. Subtle, but I'm feelin' it. ;)
the brown dress with flowers is so chic and feminine :)
http://girlynote.blogspot.com/
I would gladly wear any of these gorgeous outfits, but I'd probably pick the sweater first.
I'm counting down the days until it is sweater weather again!
Outfit #1 for sure!
I love the dresses with boots!
I have now "discovered" ASOS through this site. Not a good thing because now I want to shop a lot more!
red dress! looks like it could conceal a pasta belly easily!
I can't decide between the fist one and the last one...
http://thefunnyfunnyface.blogspot.com/
The cosy knit and jeans. I like the 70s dress too but I wore I stripey sweater and jeans on my first date with Mr TNMA - so it's got to be the first outfit!
I love the 70s inspired red dress! (I lean to the sweater and jeans too much...)
feminine silk dress with tiny flowers. definitely my style. but jeans are so comfortable! and would a silk dress be overkill?
I'm going with either #1 or #2. 1 is comfy casual, more like what I wear on a daily basis. 2 steps it up a notch, but not too much to where it feels fussy. Kind of perfect actually.
I would wear a cozy sweater or feminine dress. Love these looks! What would you wear on a date in Hawaii in the fall?
i love the last outfit!! it's so cute!!
♥ allister bee blog
2 or 4. Like the dresses, not too dressy, but a little effort. Don't like 1 for a date - would be sweating bullets in that in a restaurant...if the date was a bike ride or walk in the park, then maybe 1.
I wore a white t-shirt and olive capris on our first date with cute flats - it was August and all worked out really well :0
All of the looks are super cute, but for the occassion in question, the silk dress or the red sweater dress, depending on the weather.
WOW i can't even choose! but probably something between sweater and jeans or a dress - weather depending!
Jen
PS: love reading your blog very much :)
I'd go with the pretty silk dress! I'm just a go-to dress girl though - they're easy (one piece), flattering and girlie. Perfect for a first date!
I really love these looks, especially the #1, #3, #5. It's a hard choice but I'm really lovin' the nerdy chic sweater look. =)
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i would go with the floral silk dress for a first date and cozy sweater for the second date! always fun to show your comfortable relaxed side. love these picks!
Ooh, the silk dress, definitely. I think I'd wear the knit sweater and jeans on a fifth or sixth date, though. I'm thinking "apple orchard" or "bowling". Except I want those jeans on the model!
Silk dress with tiny flowers.
Fortunately I haven't needed a "first date" in over 20 years. :-) But if I could choose any of these outfits for a date night it would be the chic belted dress.
2 or 5. I'm really into boots with dresses and I love that only a sliver of skin shows, make them wonder what the rest looks like ;)
Options one or two! So cute.
I like the first one! I have been dreaming up some Fall outfits lately and I actually dreamed up one that I thought would look great on you!
http://ifzombiesweresupermodels.blogspot.com/2011/08/more-fall-outfit-inspiration.html
It's third from the top.
I'm visiting you from the 70s lol - so I choose the last one. I like them all (except NO to front pleated trousers) but that last is still do-able for me (& anyone).
Now. When are you finding me someone to go out with? i refuse to believe btw that any guy would text "I can't wait." But we can all dream.
xo
i don't anticipate any first dates in my future :] but on a regular date with my boy at this point in time..if it were actually fall weather i'd definitely go for the cozy rusty-orange sweater or the henley top [i wore one like that for our first date, too!] and jeans, but with the weather how it is right now, i'd have to pick the tiny-flowers sleeveless dress and bronze metallic sandals. it's still summer here in SF!
The buttons on the henley top are pretty sexy.
Ahh! I am completely in love with that Asos dress. It's on my fall wishlist! And while I don't have to worry about first dates anymore, I would definitely wear this out on the town with my loving boyfriend.
deannacaggiano.blogspot.com
I love the jeans and sweater, but I probably wouldn't wear them for a restaurant date--at least, not a first date. I think I'd go with either the belted dress or the 70s-inspired dress, but either way, I wouldn't wear boots. I can never find any that zip around my calves, and I really don't have ginormous calves. For me, boot shopping is worse than jean shopping.
But after the first date, I'd probably spend the entire fall in the jeans and sweater.
I love all of those dresses! I would probably go with the blue one for a first date.
Probably the "feminine silk dress with tiny flowers" ... now what shoes to wear?
I would wear the silk dress. I love all the small details.
fun question!!!! i would choose the first sweater or the last red dress. both with boots, but i really like them all.
i love the silk dress. so feminine and pretty. but if it was later in fall or kind of cooler, i think i'd go with the henley/skirt combo. that's pretty too :)
I definitely go with the sweater and jeans, along with a pair of cool heels. I wore an outfit similar to this out to multiple places and it's always a good choice. Functional and cute at the same time!
All of those outfits are lovely, but Fall is my FAVORITE season for one huge reason... sweater weather! My favorite outfit to wear is sweater + jeans + boots so I would definitely choose the first outfit.
I'm fond of the silk dress; however, for fall I'd probably wear the henley top - its cute, a little bit warm, but not warm enough to prevent you from wearing his coat if offered.
Oh so fun! Totally the silk dress with tiny flowers, knee high socks and tall boots.
http://bywayofney.blogspot.com
these are all incredible options, but number 1 is just calling to me. I lovvvve it. and i'm sure my date would too.
Oh my goodness, all of the above. But if I had to pick, the first one!
I have a henley obsession, so I would definitely wear that shirt. But instead of a skirt, I'd probably wear it with jeans tucked into cute boots.
My favorite fall look it actually a combination of two of yours: Chunk sweater + flowery dress. I love bringing my summer dresses into fall by layering "grandpa cardigans" and sometimes scarves over top.
I would definitely wear the first one. I love comfy-cozy, but I also like to look good! It doesn't hurt that I love knit sweaters :]
I would have to pick the first outfit. I LOVE that color.
1,3 and 4 are cute!
Oh, the belted dress. Love the style.
I hate being underdressed so I'd go with one of the dresses :)
I would 100% wear the cute belted dress. Both that outfit and the first outfit really fit my personality.
ooh...either the first or last...probably the first bc it looks the most relaxed. cute fall shopping ideas! i wore a long flowy sundress on my first date with my husband...memories.
Feminine silk dress for the first date, jeans and a sweater (with a great pair of riding boots) for the second date :)
I want to say the chic belted dress because that's what I'm attracted to, but I would end up with the silk dress on for sure. It's such a lovely collection!
The floral silk dress for sure, I basically live in A-line dresses and skirts, not really a pants person. I'd rather be over than under-dressed as a rule (although I love the first sweater - there's a similar one at J. Crew that comes in a beautiful plum color that I'm eyeing).
oooh, definately number 1!!! So So Sexy. Or maybe it's just her? :) Either way, I'm a pants and sweater kinda gal. Plus those glasses are amazing.
I'd totally wear chic belted dress as shown in the second photo. But would probably pair other than boots. xoxo
http://hellofridaybypaik.blogspot.com/
The first outfit fits my style the most but for a first date i might dress up a little more and wear a the silk dress. It's cute and if you add a cardi to it makes it perfect for fall.
The second one...the black...if I get all nervous and sweaty it will still look fabulous!!!!
The silk dress. I have tons of very girly dresses.
feminine flowered dress for sure!
I'd go with the silk dress with tiny flowers, it's so feminine and has great movement!
http://hipposandhearts.com
I love the first three outfits...however, for a first date, I'd worry that the first is too casual and then second is too dressy. So I'd probably go with third. :)
Um... I LOVE all of these. I particularly love the first look!
Kacie
http://www.acollectionofpassions.com/
Sweater and super cute jeans. In fact, that outfit should be in my wardrobe right now!
I loved that he said, "I can't wait!"
I would wear the chic belted dress...I love that look.
deffinatly the first one! I especially love her oversized glasses! I've beed dying to get a textured sweater like that. It goes well with her high waisted jeans :)
loving all of these outfits...now just to find a date!
Love,
Sincerely A
http://tokickyourheels.blogspot.com/
definitely nr 2 :-)
I would definitely wear the feminine silk dress with tiny flowers. I love the girly look!
Definitely #1. Flattering jeans are perfect for that "I didn't try too hard for you" look.
Date? It's been so long I have no idea, but I like the last outfit with the red dress best.
I love them all! But I'd go with the sweater and jeans. I like casual first dates.
I would choose either the belted dress or the dress with the little flowers. So cute and feminine. I also really like the knit sweater, too. Perhaps for a coffee date :)
Def. the jeans outfit, makes me more confident, ALWAYS wear those flashing outfits like dress when HE DOESN´T EXPECT you to, but never on the first date, shows him you want to impress him...better to be casual ;-) and shock him on another date, right??
JOANA, LOVE LOVE LOVE YOUR BLOG <3
A HUG FROM GERMANY
nadine *
the thirds dress down! so cute.
Can I take short sleeve sweater? Then I will take that first outfit;)
the silk dress for sure!!
xoxo
since it's a man you're going on a date with, it's got to be the silky dress!
to me, the other options are more the type of outfits that we women wear for our own comfort or to impress other women. men are not that complicated and would probably all vote for the feminine (but not overly girly) dress every time.
I'd go with either the chic belted dress of the silk floral print dress. I love nothing more than a feminine, pretty dress on a first date.
I would definitely wear the silk floral dress. So adorable!
either the first or last. But they're all beautiful <3
the feminine flowered dress! with a sweater because I always get cold!
probably the second or third dress, however i do love the sweater in the first, so simple..i love that!
oh i'm obsessed with the knit top and jeans. if only i looked like that model in them!
What if my date is with a woman? I'm a big fan, but it would be cool if in posts like this you could be a bit more inclusive.
I would wear the silk dress. I love the way silk feels on my skin. Its comfortable, yet it feels kind of special.
ahhh, these are all so pretty! do i really have to choose only one? :(
I loooove the silk dress! :)
belted dress would be my go-to. simple sophistication.
love the red sweater dress. though my date outfits now are a great pair of jeans and simple top or sweater-mostly cause we take out the motorcycle when we can get away!
I like all of these outfits but I wish companies would use regular sized models. Especially in the third photo the girl has virtually no waist and no chest, and I can't begin to imagine what that dress would look like on me. I'm not a big girl by any means, but I'm not a size 0 either, just a regular sized girl with curves where I'm meant to have curves. It really puts me off shopping with specific companies when they use models like this.
Second one for a nice date. I just want that first outfit regardless of occasion though, cozy and comfy looking!
Cozy sweater and jeans. No doubt! I just went on a fall clothing shopping spree, and can't wait for autumnal date nights ;)
The silk dress is calling my name. Gorgeous.
Would have to wear the 70's inspired red dress with the boots. Have always loved boots with a longish dress.
I would definitely wear the first and last + the silk dress for going out maybe with a little sweater.
I'd have to go wit the sweater and jeans. Pumpkin orange has to be one of my favorite colors.
http://lovesmodesty.blogspot.com
the silk dress! x
The silk dress, the knit sweater looks great too, but not dressy enough for a date!
OMG all the outfits are so cute. But, I'd go with the silk dress because its so pretty, yet sexy at the same time ♥
I would WANT to wear the top one, but I think the belted dress is what I'd end up with. I always feel like I have to dress up when I go on a date :)
I would wear the knit sweater but with another jeans, but if I felt like going with a dress, i would choose the silk dress.
MónicaSilva
I love the outfits in the first and last pictures but realistically, these would not look good on anyone without a model's figure. I would choose the silk dress. Great fall clothes though! I would love to see a Joanna Goddard Svpply account!
Depends on where you were having the date. If it was casual I would def go with the first one! LOVE the fall color!
I already own the glasses and wavy dark blonde hair, so I'd have to say the sweater and skinny jeans. Plus, I just so happen to have my eye on a dream-worthy sweater at the moment :)
Now all I need is an actual date! :)
silk dress so lovely with a sweet cardigan xxxx
I would DEF. go for the sexy henley.. men want to see the bod. I would RATHER wear the sweater but I don't think that's "allowed" on a first date.. too frumpy.
I would go with the first one, because the color is great and it would be warm enough for for a walk after dinner.
Silk? Tiny flowers? Moi.
xo
http://allykayler.blogspot.com
i love that orange sweater! a stunning color and perfect for a neighborhood restaurant. it would also look great with a fitted maxi skirt and pair of heels.
the 2nd or last one. boots with a dress is my uniform. looks put together, but takes me 2 minutes to dress.
Henley top.. my favorite. Looks a bit like underwear, but without bra - sexy. And you? Which would you choose?
If i was really trying to impress him i would go with the flowy flowered dress. i feel like guys love feminine sundresses.
Hmmm...why assume our cute crush is a dude?
Let's face it. It depends on the guy.
Feminine silk dress - if I'm crazy about the guy, I want to be extra touchable, and silk feels amazing. He's only allowed to put an arm around me on the first date, though. No inappropriate touching. :)
I think it's all about the dresses.
At least, if you want to score a second-date, according to this article: http://www.nypost.com/p/entertainment/fashion/single_girl_secret_weapon_736zwD5hdf7jairC9qD2HI
I'd go with the first outfit.
The "chic belted dress", of course!
Silk dress for sure!
Feminine and flattering.
i can't pick! i love them all. i'm most drawn to the sweater and jeans but my legs do NOT look like that :)
teri
www.bockting.blogspot.com
I´d go with the first outfit, always a difficult choice for me!!
I like any of the dress options. I find it interesting there's no cleavage in any of the options? I like to show a little cleave!
Belted dress! Belted dress!
I like the flirty brown dress.
For sure the knit sweater and jeans... I love it when a guy can put enough thought into his wardrobe that it doesn't seem like he overdid it. And if he just asked you out... you can't make it look like you prepared TOO much for the date of your dreams... =)
love the first one; that's totally my style. but i could also whip out the silk dress, too....
On a first date probably the sweater and pants but I love the silk dress!
One of the dresses, probably the first one :)
Definitely the first one. Comfy and chic at the same time!
Sweater and jeans all the way! I also have a history of taking guys grocery shopping as a first date (you learn SO MUCH), so perhaps I'm biased... No but seriously, it's the cutest outfit.
the 1970s dress....but for my own personal style i would wear the following:
flower dress
flannel over
fishnet/lace black tights
combat boots that fold over and show a plaid print
girly/tomboy/very me
First outfit, for sure.
Chic belted black dress and boots!
Xx
Callie
silk belted dress, definitely! it can be interpreted as dressy or more casual, and i wouldn't feel over or under dressed. this makes me so excited for fall fashion! xx hillary
http://stylecommeca.blogspot.com/
First date? Silk dress for sure. A guy wants to know you worked hard to look good for him. (But it has to look effortless at the same time...sigh.)
Adore the dress- all of them. Really, all of the outfits!
Oh my, the first one, hands down. It fits me just so. Lovely!
I'm torn... I really like the first outfit (but maybe not on a dinner date... coffee date?) so I would probably pick the silk dress with flowers! My style is all feminine and floral :)
toootally the tiny flowers dress. guys like dresses, i don't know why but even the manliest man loves a girl in a delicate little dress. this one is cute, shows some shoulder but isn't crazy fashionista. oh the fine line we'll dance for a man. i pouted when i saw it was $301.87, it's adorable and i think my husband would like it too. time to learn to sew!
the dress for sure
Definitely the top outfit. It's demure and a bit conservative which is good for a first date. However, I would wear my hair in a sexy updo to counter the outfit to show some sex appeal.
Either the jeans and sweater or the belted dress with a cozy sweater over it - perfect for the fall!
Belted dress for me! :)
i'd go with the silk dress. i think for a first date which is dinner, you should go more feminine. the first outfit would work great if you're meeting him at the local pub for a drink. italian dinner, go for the dress!
The Henley top, since when you're sitting down you still look sexy- it shows off feminine form!
have you ever made a survey on this site? you can easily make one for people to weigh in on someting like this- might be kind of fun! (survey monkey is what it's called)
love love love the first outfit, the sweater and jeans, but i guess for a first date i'd be more likely to dress up a bit more, although I guess it really depends where you're going out!
LOVE the belted dress and don't even get me started on those awesome boots.
I still have the skirt and top that I wore on my first date with Kiwi :) I am saving it for posterity!
I have a ton of floral dresses so I would pick the silk dress with tiny flowers. My bf is sick of me in floral print!
Oh my gooooodness, I cannot WAIT for fall! I just love my fall clothes. It feels like it is never going to come here in Texas, we're still hitting 100 degrees every single day! I would wear any of those as long as it meant fall had arrived :)
the feminine dress with polka dots is amazing!!! love the old school feel, very subtle romantic <3
The second one definitely. The others are cute but the second one is so flattering. I might be biased because the second one is so my style!
i have to have that sweater! AH. i'm allergic to everything but cotton! thank you, thank you, thank you!
You always post clothes that I want but cannot afford! I am but a poor college student who spends way to much money on clothes....
But, to answer your initial question, #1! Or 3... But probably 1.
Probably the knit sweater or henley top.. I never wear dresses!
Gotta go with the silk dress---I think it is perfect for a first date.
ok, yeah ... so the henley top is uber cute, and so is the silkdress ... but i'm-a-in-love with that cable-knit sweater! i guess depending what we would do would determine how dressy/not dressy i'd go.
cuuute options ... think it's time for some shopping for fall dates with the hubs!
xo
http://sarah-nadine.blogspot.com
I would either wear the sweater and jeans with some nice boots or the belted dress.
I think I would look best in the feminine dress... though I really like the idea of a sweater and cute jeans too. Sometimes I feel a little silly worrying so much about what to wear on a date; if he really likes me, it won't matter what I wear! But then again, it always helps to look my best, I feel more confident that way.
the first one! is more casual...
♥
xxxo
http://angelieeee.blogspot.com/
you can also follow me on Twitter! :) @angelieeee
well... the silk dress is the only one with any cleavage, so I'd have to go with that ;)
I love both the silk and red dresses. Wonderful.
i am so in love with that navy dress and belt! i'm purchasing immediately!
the dark belted dress (but with different colored boots)
The henley top!
I'm thinking the silk dress. It just looks so pretty, exactly how I would want to feel on a first date. Pretty.
the first one! the first one!
the 70s dress or belted dress for sure.
The belted dress or the red dress. Although I quite like the silk one too.
either the 70s inspired red dress or the belted dress - pretty but casual. don't want to give too much away! ;)
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