Shoes for a first date

denace_mennis

New Member
99
United States
Pennsylvania
Pottstown
Hello,
I think I may know already know this forum's opinion, but I am going to ask anyways.
I have done what I previously thought was impossible and secured a first date with an attractive lady. While my choice of clothing is a no brainer - chinos and a madras button-down - my choice of shoes and belt is a bit more complex (at least in my mind). While burgundy beef roll penny loafers are a simple choice, I fear they'll come off too formal (even without socks) for the trendy restaurant/bar. However, I recent got a pair of white/tan buck saddles by Allen Edmonds. If I was going out with my friends, these would be my first choice, but I don't want to come off as too eccentric (she'll figure that out eventually anyways).
Similarly for the belt, do I go with my navy/white-striped surcingle or a plain tan or brown belt.
I know I'm probably overthinking this, but would love the wisdom of this forum.
Thank you,
Dennis
 

Flanderian

Connoisseur
20,818
United States
New Jersey
Flanders
Make sure she never forgets you!


32479



Edit: OK, OK! I'll get serious. (Or at least as serious as circumstances permit.) You seem to know what you're doing. Wear whatever among those choices you most enjoy. If she likes you, she won't care, but on the other hand, if she doesn't like you, she still won't care!

Double Edit: As an old man to a younger one; be who you are. It's better if she hates who you are than loves who you're not. Because eventually, she'll hate that one too.
 
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Tod Hackett

Active Member with Corp. Privileges
320
While burgundy beef roll penny loafers are a simple choice, I fear they'll come off too formal (even without socks) for the trendy restaurant/bar.
Perfect choice in my none too humble opinion and no they won't.

be who you are. It's better if she hates who you are than loves who you're not. Because eventually, she'll hate that one too.
Sage advice.

You are perfectly correct though about their likes and dislikes - the last time a woman complemented me on my shoes I was wearing an absolutely beat-to-hell pair of dirty bucks.

Go figure...
 

Fading Fast

Connoisseur
7,340
United States
New York
NY
You absolutely should be who you are, but nobody leads on a first date with every quirk and eccentricity that they have. To that end, and sincerely in the spirt of wanting to see you have a great first date - are you sure a madras shirt is the way to go as some see that as a bit out there.

Penny loafers or bucks sound find to me - you're a trad dresser and no need to hide that - but just as I wouldn't wear a Fair Isle or critter pants on a first date (there's time for that), I might go with a solid shirt and save the madras for a bit down the line.

And as noted above by both smart poster, most importantly, be who you are. I can only emphasis that you should present your personality and thoughts true to you (as Flanderian said) - but toning down your style choices for date one is not misrepresentation.
 

FLMike

Connoisseur
5,773
United States
FL
West Coast
I agree with all the comments so far, but especially FF’s. The penny loafers sans socks sounds fine, but I’d consider swapping the madras for a button-down sport shirt of some type. Doesn’t necessarily have to be solid...I’d personally go with a broadcloth check of some kind. Nothing wrong with madras, of course, but given your comment about not coming off too eccentric right out of the gates, there might be some better options.

Since you started out be saying you think you already know the Forum’s opinion, I’m curious as to what response you expected to get?
 

Shaver

Connoisseur
10,725
England
.
Manchester
This is an important subject and, if you will permit me, you seem rather befuddled.

Your old uncle Shaver, happily unmarried at 54 years young, has been on the *ahem* occasional first date, of which few were entirely disappointing.

Are you looking for a wife or a good time? If it is the former then I urge you to reconsider your goals but if it is the latter then, here goes:

Be impeccably groomed; clean shaven, face moisturised, nails manicured, hair perfectly styled.

Dress smart and crisp but bland; dark blue jacket, pale blue shirt, light chinos and brown brogues.

Go to a bar (not a restaurant - avoid providing dinner on a first date) and pay for the drinks.

Exude confidence, appear relaxed and make any decisions which might be required.

Ask questions. Females are never happier than when they are talking about themselves. Feign interest, however difficult this may be. A happy female is a receptive female.

Escalate. This female agreed to a date and so intercourse has already been approved as a possibility. Demonstrate that her judgement was sound.

Good luck!
 

TKI67

Senior Member
862
United States
Texas
Austin
I agree with sockless loafers. If you stick with the Madras shirt, go with the brown belt. IMHO a striped surcingle will not work with Madras. However, a solid surcingle would. The striped surcingle would work with a broadcloth check. Have fun!
 

denace_mennis

New Member
99
United States
Pennsylvania
Pottstown
Thanks for the suggestions. I figured this Forum would suggest the penny loafers. My reasoning for the madras shirt is that its inherently a more casual shirt but a checked or striped button-down is probably a better option.
 

Oldsport

Senior Member
974
United States
New Jersey
Swedesboro
Day or evening date? If evening i’d Wear a more conversation shirt as you suggested. At any time I would not wear the saddle shoes AND the madras shirt together on first date. It’s not 1955 ....
 

Flanderian

Connoisseur
20,818
United States
New Jersey
Flanders
Perfect choice in my none too humble opinion and no they won't.



Sage advice.

You are perfectly correct though about their likes and dislikes - the last time a woman complemented me on my shoes I was wearing an absolutely beat-to-hell pair of dirty bucks.

Go figure...
Better yet, my wife might tell me how how "nice" she thinks a particular article of clothing I'm wearing looks, and a few weeks later complain, "You know I don't like things like that."

Perhaps brother Shaver is onto something, as seeking consistency among a female's perceptions seems to be something of a fool's errand. Might as well play the beau, because within a short time she'll have changed her mind about what she prefers anyway.