Guest Posts

  • What to Wear: On 3 Key Dates  by fashion blogger Sara Zucker

What to Wear: On 3 Key Dates by fashion blogger Sara Zucker

2nd July 2013
farpitzs1Please welcome the lovely Sara Zucker to Style Girlfriend!

A super-cool fashion blogger and all-around great gal, I’ve been a fan of Sara’s style and her writing since before we were friends IRL (that’s “in real life” if you don’t know…now ya know..). As a single lady who’s practically a pro at online dating here in the city, I asked her to come up with a few outfits she’d love to see a guy show up wearing on a date offline.

She’s a little nervous, so make sure to show her some patented SG reader love in the comments!


Hi, I’m Sara and I write a blog of fashion-based thoughts at As your e-yente, I’ll dispense some sage advice regarding what to wear on a few very different dates, but first, you should know that I have guest post anxiety. “Megan’s readers are so stylish! What if they don’t approve of my choices?”

Despite the grey hairs, I threw caution to the wind and created three outfits, all of which I would love to see a man wearing on a pivotal early date. In doing so, how could I possibly disappoint you if I stay cocooned in my selfish, self-centered, ‘independent woman’ bubble? Please also keep in mind that while some of my readers consider me an expert in both fashion and dating, I am single and frequently wear sweatpants. Read on, new friends!


The “Are They Normal?” Coffee Date

No need to get fancy on this date; be casz and keep clothing simple. You can add personality with footwear and accessory choices. I would definitely suggest that you avoid reaching for your favorite messenger bag, mainly because it is massive and completely unnecessary for an occasion that will just involve scones, espresso, and (hopefully) good conversation.

Your companion is going to think that you work all the time and/or don’t have a home to get back to if you show up toting your whole life in that substantial, cross-body, canvas/nylon situation. Do not be afraid of employing a leather pouch for essentials! You will retain your masculinity while still toting around your necessities – it is a win-win.

Shown: Quiksilver t-shirt, Topman slim jeans, Club Monaco Pouch, Puma Sneakers


The Before-You-Get-Nekkid Third Date

Peonies are essential in the attempt to truly woo your date for the following reasons: they are a token of affection (points for being thoughtful and generous) they aren’t roses (points for being unique), and they smell nice (points for nice smells). You may also be thinking “Sara, salmon pants?” and that is a totally logical thought, but I figure, why not get a little sassy with your clothing before you get a little sassy without them, am I right? The overall look shows that you care about the occasion – you could, in fact, experience a makeout tonight – without getting too ‘black tie’ and making your companion feel under-dressed. Get it, boy!

Shown: A bouquet of flowers (for obvious reasons), Fred Perry shirt, Ted Baker chinos, Gobi chukka boots


The Day-to-Night Date

Oh, you want to pull out all the stops, do you? This person is a total keeper and you plan to bring them home to Mom? That is awesome. You go! With that in mind, this sort of hours-long date requires a backpack because they are all the rage right now and you, the fashion-minded male, care about the rage. Sneakers are also a good call as said date may require climbing mountains – or just walking around a lot. Just be sure to maintain eye contact throughout because if you notice your companion fading, you may want to put some stops back, thank them for their time, and escort them home.

Shown: Billabong pullover, Polo by Ralph Lauren trousers, Hugo Boss t-shirt, Nike sneakers, Everlane backpack

Tell us:

Which date do you stress the most over your outfit? The first meeting? The first time you get introduced to the fam? Sound off in the comments!

  • Chris Rogers

    Definitely first date is the one I stress the most over clothing wise! Great post Sara, I really liked your “third date” outfit and it reminds me I need to find some salmon pants. Also, the humor wrapped into your post was great and provided a good laugh this morning!

    • sarazucker

      Salmon it up, Chris!

    • Style Girlfriend

      Totally agree, Chris. That’s why I tracked her down in New York so we could be friends; she’s hilarious!

  • Enrique Ollero

    Great post! I love that tee for the first date. I hadn’t considered skate/surf style in years, but that Quiksilver shirt has turned me around on that entirely. And I love the second look. A good US option for those pants would be the Dockers slim khakis in apple butter:
    I’m wearing a pair right now and I love ‘em!

    As for which date I would stress over, it was definitely meeting the parents. I always worried about making the right impression and would tend to wear things that I had in my wardrobe as a holdover from prep school but would never wear normally. I mean, I’d wear a refined version of it now, but back when I was wearing Quiksilver, being in the uber preppy clothes felt wrong.

    • average joe

      Sometimes meeting the parents is stressful because she’s taking the relationship to another level while you’re trying to cool things off…vs…Meeting the parents and hoping they like you type of stress

      • sarazucker

        Meeting the fam in general is enough to produce hives. Lots of potential judgement!

    • sarazucker

      Proof that apple butter is both tasty on your bread AND your legs. Great call-out re: US shipping.

  • average joe

    A couple of things:

    My wife is a florist and I concur that peonies are an excellent choice. They are usually only available in the spring (that’s their season) and are cheaper the farther north you live, as they are a cool weather flower.

    I love all the outfit choices, albeit even if the 3rd one is kind of casual. Those boots on the 2nd one, and those pants…all really solid looks.

    I gotta ask though, what’s with the backpacks these days? Even if I owned one, what would I put into my backpack?

    • sarazucker

      I love me a backpack, Joe, esPECially as a commuter. Hands-free is where it’s at. Plus, going to the gym before work requires me to pack everything for day-to-night in one bag.

      • average joe

        you know us suburban folk…our backpack is our car

        • Style Girlfriend

          Honestly, I do forget that sometimes. I’m sure Sara does too!

    • Enrique Ollero

      I don’t always carry a bag, and when I do it’s a shoulder bag rather than a backpack, but here’s what I usually keep in there: a pen, pencil, stylus, small sketchbook, ipad, streaming hard drive, small umbrella, water bottle, and keys. Occassionally I’ll also carry a spare tie or bow tie and pocket square.

    • Derric

      Some flower-on-a-date questions:
      -She’s going to be happy to hold it during the date, right? I only keep my wallet, phone, and keys on me and don’t like having much else on me, so I just want to get the okay that (most) women will be fine carrying the flower along with their normal things.
      -What other flowers work well for dates and for general flower giving? Sunflowers have worked for me but I’m always open to other things.

      • average joe

        When ordering flowers that are going to be delivered by the florist, avoid asking for specific flowers. Unless you have some major flower knowledge, asking for roses and calla lillies (example) is just going to handicap the designer because they’ll trying to comply with your request and might not be able to use the other flowers they have in stock that you might not know about. Instead, ask for a “modern arrangement” or a “tropical arrangement” Unless your ordering from a country-down-home florist they’ll know exactly what you mean. (You can google those two terms and get an idea as to what they look like) If you are sending flowers to some one in a the country or more rural area, use They let you pick your style and have a great picture selection that gives you an idea of what you’re sending. Expect to spend between $80-$150. If your budget is only $35, save your money and go to the grocery store and pick up a bouquet for 10 bucks…remember at the end of the day, it is the thought that counts! I like your sunflower thing too. It’s the alternative to roses vibe. And if you are bringing her flowers in person, shoot for carrying 3 or 4 flowers that you can hand to her when you pick her up. Just make sure she has a vase that she can put them in (with water) before you leave for your date. If you’re meeting her at the restaurant, skip bringing her flowers there. It’s awkward – where do you put them, etc. Other options besides sunflowers are: calla lillies, peony, tulips, hydrangeas, gerbera daisies. Keep in mind that most arrangements will include multiple varieties of flowers.But if you wanted to hand her a few flowers like I mentioned above, 3 or 4 gerbara’s work great!

        • Style Girlfriend

          *I* learned so much in this comment; thanks Joe!!

  • A Gentleman

    What would Sara think if I show up with a sport coat and a nice shirt for that coffee date and third date?

    • sarazucker

      Sara would be impressed by your dapper style, but would feel slightly casual as she doesn’t even own a blazer (the female “sport coat”).

  • Matt M

    Really like the 3rd date outfit and flower suggestion. I can get on board with the first one, but the contrast color of the chest pocket throws me off. The day to night date on the other hand…. seems like something you see a high schooler wearing. Sneakers, a hoodie, and a backpack? Surely we can do better than that.

  • Junior

    So we’ve jumped to short sleeves button ups getting us laid…….

    • hornsup84

      You’d be surprised — I was. I picked one up from JCrew recently and have gotten lots of compliments from girls and guys alike. And for the agists, I’m in my late 20s so it works beyond college.

      I wouldn’t wear a lot of the stuff above, as it’s a bit more skater/alternative than my usual preppy casual look, but have been trying to work in some more casual styles on occasion. To each his own — do what works for you!


    Great post! I really like your writing style, and hope to see you ‘guest-writing’ more often! I really like the looks as well…personally, I tend to go a bit more formal/dressed up even in my day-to-day wear, but there is definitely something to be said for being able to look sharp while dressed down. Also, my girlfriend of 3 years loves my dressier style, but I know even she gets frustrated at times feeling underdressed (or pressured to dress up when she’d rather be casual), so it’s key to have some more relaxed (but still suave) options to make everyone happy.

    • sarazucker

      Thanks for the feedback and support, Adam! Totally agree with you — it is a feat to master both “dressy” and “casual,” particularly with regard to dating.

    • Style Girlfriend

      Like like like! I hope to have Sara back plenty in the future! Like if you agree all!

    • average joe

      yeah the writing style was good…i definitely like it

  • Jason Jawoozee

    in whose world is a leather pouch normal and masculine? sara, we know you have a working relationship with club monaco but come-on-now. & day-to-night sneakers? they’re not even appropriate for day.

    • sarazucker

      I found a leather pouch more appropriate for a date than a messenger bag. Also, just an FYI: no one paid me to sponsor any item in this post, so the brand is irrelevant.

      • Aaron

        Not being paid directly does not preclude having some level of bias (conscious or unconscious) due to an existing relationship.

        • sarazucker

          True, of course. But all “working relationships” aside, I liked the Club Monaco pouch (as well as many other things Club Monaco designs), which is why I highlighted it.

  • Aaron

    These all look skewed to an extremely young crowd, I’m not sure anyone post college would/should wear most of these things on a date.

    • Junior

      Disagree, a younger crowd wouldn’t be able to tell time on a watch that uses those moving stick thingies

      • lazy_panda

        =O …don’t you know that young people pull out their phones when they want to know the time? That wrist thingie with its unreadable face is all for looking hip!

    • Enrique Ollero

      I can see them skewing younger, especially the hoodie and backpack combo, but I don’t see anything wrong with anyone over 21 wearing a lot of these items, especially on casual dates/settings in the summer.

      • Junior

        In my mind, the outfit should be produced based on the type of date and the lady (or gentleman) you’re meeting. It could be date one or 100, and you could wear a suit or a t-shirt. If the first date is cocktails after work with a professional woman I don’t see it working out with your best t-shirt from Pac Sun. However, if you’re going to rent a couple bikes and cruise around the park, there is nothing wrong with a NICE t-shirt or wearing a backpack for convenience.

    • Tod C

      Sure but we also need to remember this is a dating post which us married guys aren’t the target for. I did enjoy it however and it did help to remind me that as I am dressy for work I sometimes don’t dress it down enough when we go out (I am married to a yoga instructor). So thanks for the perspective Sara.

      Having said that I always appreciate Gabi’s “young guys only” caveats and wouldn’t mind advice for things like “not looking like an old guy who never grew up”, “how to look professional when your boss is a woman” or “what a mature lady likes”.

      Ask your Mom next time you are home Megan …

      • Aaron

        Your first sentence here doesn’t really make sense. You can be, as many people are, non-married, actively dating, and not extremely young. I’m in my 30′s and I’m not married.

        • Tod C

          Point taken (I married in my 20s so sometimes I forget). I guess my point is more that sometimes these posts are geared at people other than us and we have to look at it with that in mind.

  • West

    Kinda cool outfits, but this is like, for eighteen year olds dating—who are apparently encouraged to have sex after having gone on three dates.


    • Style Girlfriend

      But you think judging other consenting adults’ decisions about what to do with their own bodies is classy?

      • Joe



    I miss getting style advice from this site for men, not boys

  • DanPatrickFlores

    I like many of the pieces for the first two outfits, for example: slim jeans, a fitted polo, and either chukkas or white low-top JPs are my go-to for a first date.

    As for stressing on outfits, I think the most I would be concerned about is meeting the parents or close friends. I want to look put together, but not look like I tried too hard.

    …and by the way, “I am single and frequently wear sweatpants.” geez, message received, you don’t have to twist my arm ;)

  • Crane

    Big fan of the second look. Salmon pants? Awesome. Im a big fan of colored chinos. Keep on Keepin on Sara Zucker.

  • sagehillbilly

    Yesssss, more Yiddish please!

  • Jim Alrutz

    I like the writing style a lot, but I agree with the comments that these outfits do seem to skew towards a younger crowd. I’m part of that younger crowd, being in college, but my personal style is more dressy so there’s not a lot I can take from this (I default to a button-up unless I know I’m sweating, like at marching band practice, or it’s the end of the day at home).

  • Martin

    All these “Get of my lawn!” posts remind me of the great workout wear discussion.

    Good times.

    • Style Girlfriend

      Martin, you are the best. <3 you forevvs

  • Eric

    I dig the second look, pretty much my exact style this past spring.

    I think Sara might be forgetting that men’s clothes actually have functional pockets (the women in my life are always saying how useless girl’s pockets are, if they’re even present). Having to carry a little leather pouch thing in my hand is actually more of a pain than not having it at all.
    Almost any time I leave the house I’m carrying a cell phone, Swiss army knife, keys, bandanna, pen, and wallet. These distribute quite nicely between my pants pockets without any need for a special accessory to carry them.

    I see that Sara’s getting a lot of flak for some of these choices, but I want to point out that this post is HER opinion, and it was nice of her to take time out of her day to share with us. If you’ve got a problem with the Nike high-tops, don’t wear them. Simple as that.

    • Style Girlfriend

      Thanks for your helpful POV Eric! Yes, it WAS very nice of Sara to take time out of her day to write this post, and her opinion is just that – her opinion. No reason anyone should be called out for sharing theirs.

      And that’s some interesting gear you keep with you! What’s the bandanna for?

      • Eric

        I started carrying the bandanna when I was hiking with a lady friend and she fell in some mud. I had one in the bag that I always take hiking, so I gave it to her to clean her pant leg off (in my head it was a perfect knight in shining armor moment). So I figured it’d be useful to have one in my pocket even if I’m not hiking, and I use it to dry my hands or clean my shoes, anything you might need a rag for.

        • Style Girlfriend

          That’s pretty much the best explanation ever. So chivalrous!

  • Erik Harder

    Sorry I’m late to the party here, but Sara totally just got a new reader. Her personality was awesome coming through in her writing and I totally appreciate the casz (omg so many points for that) outfit suggestions.

    • sarazucker

      Thanks, Erik! You rule.

  • Sam Boja

    Its entertaining reading the responses from the “old guys” talking about what the “young guys” should or should not be wearing. This article is probably not for you
    being that these radical clothing concepts are above your sense of style. Could it be that you should not be reading “hip” articles to give you pointers on a coffee date? You guys should know what to do by now, not to even be commenting on things you
    obviously don’t get. Just sayn’

    • Style Girlfriend

      Thank you for your perspective, Sam!!

  • JM

    These are perfect choices for the general college kid ( considering I am one) that being said I would not wear #1 or #3 . Way too casual and a tad immature. Three would be perfect with a nylon/cotton bomber and a canvas/leather messenger. And #1 with a Timex and a NATO strap from J crew instead of that bright green thing.

  • Ryan

    I really like all 3 outfit combinations. I don’t think it skews young either…high-top sneakers and more casual shoes can be worn by anyone, not just someone in college. It’s all about the time/place to wear them, and on an outdoors date (zoo, park, etc.) sneakers are more comfortable and appropriate (if done right) than dress shoes.

    Great piece by Sara, thanks!

    • Style Girlfriend

      Agreed, I think she did a great job!

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