thefleets said: Do you have a preference to skinny or classic 3 1/2" ties? And why?

I prefer skinny ties because I don’t like the “fatness” that comes with a 3 1/2 tie.  With that being said, I don’t like skinny ties that are super skinny, only that they are less bulky than a traditional one.  If that even makes sense?

-Dean

duxburyprep said: It was a little chilly today, yesterday a little warmer. I broke out my tweed blazer today and I was crazy warm. Layers my man, layers! Cheers, Chase

That it was!  I think I’ll be wearing most of my clothes onto the plane this evening.  hope you have a great week, Chase!

-Dean

Anonymous said: What are your favorite tv shows and movies to watch on a lazy day? If you even have lazy days haha.

What is this “lazy day” you speak of?  

At the moment, there are only two shows I regularly watch:  Revenge & Downton Abbey.  I love watching Flipping Out With Jeff Lewis, but the seasons are rarely more than 10 episodes or so long…

-Dean

empire--falls said: Hi Dean. I'm a senior in high school and most of my friends are in college so I visit them every other weekend. I've never been a big party person or drinker but this weekend they took me to a party with strangers and alcohol. I was extremely uncomfortable because I wasn't drinking. I'm not very fond of alcohol but I felt judged because of this. Alcohol or drugs have never appealed to me but I thought a college party would ease those feelings. How did you confront college parties?

Well…I have a pretty low BS tolerator so if something/someone is making me uncomfortable I usually don’t put up with it.  In college, I rarely go/went to the “typical party” because it’s was never something that I enjoyed.  I certainly don’t look down or judge people who do, only that it’s not for me.

My advice to you is to never let anyone (even a friend) make you feel pressured to drink, do drugs, or whatever else teenagers are doing these days.  I know a lot of people who actually go to parties and don’t drink a drop of alcohol because they either don’t like the taste of it or would prefer to be coherent throughout the evening.  If your friends can’t respect that, then it might be time to make a new friend group.

Overall, do what YOU feel comfortable with.  Drinking and doing drugs at a young age is NEVER a smart idea as the risk of harming yourself - or someone else - is not worth the couple hours of “fun” you’ll have.

I’m not for sure how much this helped, but please write in if you want to talk about this more.

PS:  If any readers have worthwhile advice to share for this young lady, please do!

-Dean

Anonymous said: Hello dean! I have a question about relationships in high school. I am a senior in high school, and a female. Over the past year I have gotten very close to a younger boy, who is a sophomore this year. He is very sweet, and so very kind to me. Would it be wrong to date him? I adore him very much, but i'm afraid that it is frowned upon.

My advice?  Do what your gut tells you.  I’ve always been a believer in the idea that age is just a number…

-Dean

Anonymous said: I had my GWU interview on Friday and I cried!!! 😭😫

What?? Why??  I’m sure it went far better than you thought…

-Dean

duxburyprep said: Hey at least your name and face were put together on this end! Plus I had a meeting with a client to get to, but who knows next year? Hope you liked Boston, we are awful proud of it!

Well, I’m glad I was at least spotted.  Hopefully our paths will eventually cross in the near future.  Best of luck with the brand and all of your endeavors! 

PS:  Boston was AWESOME, but a bit cold.

-Dean

duxburyprep said: Dean, thank you so much for that info. Ya we are going with the sole proprietorship. Everything is helpful when you are starting a company. I was at the HOCR and wanted to meet you, but you were so busy with other people I never got the chance, but I love what you do man. It's great stuff!

Of course!  No problem at all.  Ahh you should have came up and said hello!  It was so great getting to put names to faces this weekend.

-Dean

Anonymous said: Dean Im in need of some advice. I'm distracted by sales on chino shorts and sandals when I need to save for a new coat and bean boots. Do I take advantage of the amazing sales going on on last seasons stuff or do I just save for the upcoming/current season?

In my opinion, I would buy what you NEED.  If you “need” a new coat and Bean Boots for the upcoming season, then I would save your money and invest in said pieces.  

With that being said, it’s definitely wise to score items for the warmer months on discount, but don’t let yourself get carried away as “it’s on sale” is not always a legitimate excuse to purchase something.

-Dean

"This is your Sunday evening reminder that you can handle whatever this week throws at you."

(Source: ProperKidProblems.com)

regattasandreppties:

Had a good time at the regatta today with Dean of properkidproblems

regattasandreppties:

Had a good time at the regatta today with Dean of properkidproblems

Anonymous said: Thoughts on Land's End Hyde Park oxfords? I think it's the best supima cotton Oxford the price.

I like!  Lands’ End has some really great pieces that are extremely affordable.  I’ll have to consider doing a post on them some time.

-Dean

Anonymous said: What's with your sudden interest in hats? Loose it. Let the Kevin Jonas hair fly (;

Ha!  It’s really been out of convenience for the most part.  For instance, since it was windy all weekend here in Boston I figured it’d be easier to just throw on a ball cap everyday instead of letting my hair turn into something that would resemble a bird’s nest.  You can expect future pictures with my regular “do.”

-Dean

Not sure about all the race results, but this weekend’s outcome was definitely a success. Great meeting all of those that came to the @brooksbrothers tent!

Not sure about all the race results, but this weekend’s outcome was definitely a success. Great meeting all of those that came to the @brooksbrothers tent!

Anonymous said: Hey Dean! Im in the market for a pair of women's riding boots. I really like the boots Tory Burch has but he price is unrealistic for my budget, do you happen to know of any boots with a similar style that are more affordable? Thank you for your time! :)

I don’t know what your budget is, but what about the “Jersey Riding Boot" by Naturalizer?  I don’t know too much about women’s clothing so I would take my suggestion with a grain of salt…

-Dean