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First Date With Younger Lady - What to Wear?

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burnedandfrozen

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Discussion starter · #1 ·
Hi Guys,
I've got a date this Sat. night with a...uh...younger woman. I'm 35 she's 22. I'm not thrilled with the age difference but how I ended up in this situation is another topic. Normally I'd reach for a sportcoat, but I'm not sure if this is a good idea. I don't know this young woman very well, but she seems very sweet and she is very atractive so I'd be open to seeing her in the future if things go well Sat. and I can get past the age difference. I just don't want to look like her dad so that's why I'm thinking of going for a simple sweater, flat front pants and maybe a pair of my beloved spectators. We're just going to see a scary movie and grab some pasta at a nearby resturant. Yeah, not real original I know, but I want to keep things very casual and easy. Or maybe a leather sportcoat under a T-shirt and jeans? I can't quite figure why she wanted to go out with me in the first place...I asked her if she had any problems with the age difference and she said no. Maybe she's getting tired of the guys her age and their imaturity and hip-hop look? Thanks for any advice.
Regards,
Mark
 
#5 ·
quote:Originally posted by burnedandfrozen
Maybe she's getting tired of the guys her age and their imaturity and hip-hop look? Thanks for any advice.
Regards,
Mark
Click to expand...
Maybe she's hoping to be treated like an adult by someone who looks like an adult. Why would you treat her differently than any other person you would ask out? Sorry I'm not phrasing this well I'm sure. I really don't mean this to be critical or mean spirited, it's not intended that way.
Cheers
 
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#6 ·
I think, given your description of the date, your first outfit works really well (although I would ditch the spectators in favor of something more conservative for a first date). The second outfit is probably equally appropriate, assuming the restaurant is a more casual place, but I'm honestly not sure whether leather sportcoats are still "in."

Also, it's hard to tell what kind of a person your date is. Her interests (e.g. dancing versus quiet walks on the beach) might also dictate your wardrobe, assuming that you're dressing to impress, at least in part.

At any rate, good luck!
 
#7 ·
I'd definitely save the spectators for the 6 or 7th date, after you've got her hooked. I'd stick to "tried and true" clothes -- well dressed with nice leather shoes, but nothing that shows off your dandy side too much (i.e., don't wear a blazer w/pocket square to go to a casual movie/spaghetti night).
 
#10 ·
Just wanted to add not to sweat the age difference. It's not that unusual, especially where the girl is younger.

Just don't try to dress five years younger to the point of exaggerating the age difference though. :) Good luck!
 
#11 ·
Let me say at the outset that I do not think I am going to be able to give you any real 'advice'. I have no experience of such a situation and little knowledge of American ways. But I was taken with your appeal and offer a couple of comments on your text.

13 years is not such a huge age difference, or won't be if it works out and when you are 40 and she is 27. You are too young to be her Dad and you certainly don't want to dress like him. Presumably you have met already so she has some idea of your style. I'd have thought you will not want to surprise her by suddenly appearing like some one else. Assuming she hasn't already seen you in tweed or leather I think it would be best to avoid both.

It is you she wants to go out with so I wouldn't worry about her having some sort of problem with younger men. Have some confidence.

It sounds to me that your dress plan sounds generally fine for the evening you propose.

But what about these 'beloved spectators'? I think they are the reason you are concerned (and what inspired me to comment). These point to some other side of your personality that maybe you are used to playing down - even concealing. How she is going to take this you are wondering? How is she going to take the combination of spectators and a horror film? Should you opt for something different on a first date or is it better to intrigue her with your mysterious side?

Trimmer
 
#12 ·
I'd be tempted to ditch the sweater and go with an open collared dress shirt with the leather jacket, and pair it with nice shoes and either jeans or flat-fronts as you described. As long as you wear decent shoes and tuck the shirt in, you won't look too much like the stereotypical "American Jackass" that has been so derided recently. In addition, you could throw on a natty scarf to perk things up and keep you warm; if it's cashmere, she's bound to want to stroke it ;)
 
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#13 ·
Whatever you do, don't stray too far from your usual style. Remember the scene in Lost in Translation, where Bill Murray picks up Scarlett Johansson wearing some awful designerish getup because he wanted to look younger? You don't want that. Furthermore, since you don't know what she is attracted to/sees in you, you don't have much to lose by being true to yourself. Anyway, good luck!
 
#14 ·
As someone in his 40s who has dated 25 year olds I'll say you're not lucky at all. Good luck. You're gonna need it but give me a 40 year old any day.

If you wanna impress her, square toed shoes, an untucked shirt with stripes, jeans and a Tag Huer watch. Take her to a chain drinks place: TGIG or Dave and Busters. Try not to spend more than 40 bucks on her.
 
Discussion starter · #15 ·
Thanks for the quick replies folks. It's just that when one dresses in a Trad. manner like most of us do, it can make one look oh how should I put this, not older per say but just more mature and settled. This young woman may have dated guys her age that still insist on wearing a backwards baseball cap out on their dates. So I can see why she might be open to going out with an older guy. Still, I just don't want to sit across from her and have her think I dress like her father or uncle. However, I also don't want to dress in something completely inappropriate for my age either. Being that she works in the same place I do but different area, at least I know she's not going out with me for my money!!LOL.
 
#16 ·
quote:Originally posted by burnedandfrozen

I've got a date this Sat. night with a...uh...younger woman. I'm 35 she's 22. (...) Thanks for any advice.
Click to expand...
I would propose a nice untucked striped shirt with pointed collar, a black jeans and these truly great and stylish Kenneth Cole square-toes (https://www.zappos.com/images/801/124801/52755-d.jpg).

No, seriously: I think you should go for the jeans, the shirt (maybe a polo shirt, alternatively?) and some nice leather shoes. If you live in a colder climate, I would additionally propose a fitted (!!) cashmere coat and striped scarf for outside. I agree with my fellow participants that spectators would make you look older; go either for some nice tan penny loafers or chestnut chelsea boots. Or maybe a wholecut (that's stylish!). Should look sharp.

Cheers,
A.
 
#18 ·
There are so many factors that come into play, trying to answer this question. My opinion, is based on what her "actual" age is. Is she a young 22 and you're just going out because she's hot and you want to brag, then do the jeans and striped shirt or ribbed fitted sweater. If she is a mature 22 year old and will be dressed nicely herself, I would say at least khakis and a button shirt. Throw a light windbreaker instead of a sport coat over it to keep it casual.
 
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#19 ·
quote:Originally posted by tintin

As someone in his 40s who has dated 25 year olds I'll say you're not lucky at all. Good luck. You're gonna need it but give me a 40 year old any day.

If you wanna impress her, square toed shoes, an untucked shirt with stripes, jeans and a Tag Huer watch. Take her to a chain drinks place: TGIG or Dave and Busters. Try not to spend more than 40 bucks on her.
Click to expand...
To a certain degree, I'm going to disagree with this one. Yes there are girls who are too young to know much, no different than the younger guys they typically date.

Girls often look to the older guy because he seems to have it together. He represents solidity, maturity, and security. A man who knows who he is, where he wants to go, and has demonstrated a record of achievement. In very general terms, those are frequently the grounds for attraction across age gulfs. Look at the men who are type cast as this style in movies, Harrison Ford and George Clooney. Neither seem like Adonis, but they have that "all together" thing going in the characters they often portray.

In my opinion, this is what you should convey to the younger girl. Sure, be every bit as fun loving, humorous, and enjoyable as the best 22 year old she has gone out with before. But, do it as the confident, secure, experienced man she has likely not dated up until this time. For instance, she will appreciate your social stories don't include numerous references to hangovers and the implied vomiting. You can go into a restaurant and know how to handle the experience. Probably you have traveled to places she would enjoy visiting (but don't be a braggart, that's for those lacking experience in life). Most of all, your not going to be some random guy fumbling around in life nervously hoping to get lucky (well, at least portray that).

Dress the part. What would you typically wear, assuming you are already dressing right. Don't look like screwed up older guy having an early mid-life. Have fun. Most of us here sound a bit envious.
 
#20 ·
Gentlemen

Wear what you like?
I agree with mpcsb, wear what an adult man would wear.
I am 54, dated a lass that was 21, last month.
We are still dating.
She loves me for being a nice looking, distinguished man.
All my lady friends, are much younger than yourself.
So I can share a little wisdom, and know-how.

Enjoy your life


Jimmy
 
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