Category Archives: What to Wear Where

What to Wear for the Kentucky Derby

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Even if you’re not going to the Derby itself, but rather watching at home or a party, I highly recommend dressing for the occasion. There are plenty of options for Derby gear, suitable for everyone from the most conservative guys to those with a little more style aplomb. Here are a three outfits to consider, from least to most dialed:

Men's Personal Shopper: Kentucky Derby Style

  1. Navy blazer, chinos or shorts, light colored dress shirt, and bright or pastel colored tie or bowtie (extra points for coordinating pocket square).
  2. Men's Personal Shopper: Kentucky Derby StyleSeersucker suit or jacket, white shirt, open collar, pocket square (in either a traditional/neutral color like navy or a bright/pastel).
  3. Men's Image Consultant: Kentucky Derby StyleBrightly colored pants, light colored shirt and sportcoat, pastel tie and pocket square.

Men's Image Consultant: Kentucky Derby Style

Hats, of course, an optional bonus 😉



images via,,

Dating Profile Contest Winners Unveiled!

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I held a contest a few weeks ago, along with dating coach Sarah Jones, to review the dating profiles of 3 guys’ from our email lists. We had some great entries, and I’m excited to be sharing our commentary with you. Huge props to these guys for entering the contest — it takes some serious cojones to put yourself out there like this. If you’re not on my newsletter list, I highly recommend getting yourself on there, as I frequently hold contests and share commentary in my newsletters that you won’t find me posting about anywhere else. Read on for our reviews…

Men's Style Advice: Dating ProfilesJulie:

These pictures display a great mix of expressions and moods. It shows you as a well-rounded guy, and I like that you included one with more of your body as well as just your face. What would make your profile pix an even more thorough combination, is if instead of using all of them from the same scene, you included pictures from different situations. That gives you a chance to show yourself in various situations where you show up in your life, and how you dress for each one.

Overall, you have a friendly, open and smart look, which is appealing. I like that the images aren’t too posed — you come across as very “real” in them. Great shirt choice, too. The grey picks up nicely on the silver tones in your hair, and the rolled up sleeves make you look approachable.

I do have a couple of suggestions for you:

  1. In the two closeup shots, your dark glasses frames obstruct your eyes. Most women find eyes extremely appealing (they’re often the first thing people look at in others’ faces), and with the glasses impeding my view of them, I lose that connection.
  2. There are a few red spots on your face, which can be a little distracting to the viewer. I’d love for you to clear them up so that we can focus on everything else that’s so great about these shots. Here is a blemish patch that I’ve found works well for my clients, and it’s only $5.

Great work!


Hi there! Excellent job right off the bat talking about her and her values. Intelligence, openness, and playfulness. “Deliriously exciting” — so good! Every woman wants to have that effect on a man. 🙂

I love the “stimulating conversations that would last all night…” — very, very good. See what you did there? You incorporated “stimulating” with “lasting all night.” Very sexy and yet subtle. It is referring to “conversations” after all, ahem (straightens collar). 😉

In that second paragraph, you go more into what those initial values you mentioned in her say about your relating with each other and your experience of her as well as what you’re like as a man.

Then you segue into who you are, and I love that you’re not overly humble. You’re honestly stating what you enjoy about yourself — so important, as it sets the tone for her to enjoy you too!

In the end, go into a little more sensual detail about your favorite kinds of gigs and museums and where you’d like to take HER.

Also, maybe replace the last line, “If this sort of man would rock your world, get in touch as I’d love to hear from you,” with something like, “If you’re half as excited reading this as I was writing it, message me. I’d love to hear from you.”

It feels more natural and playfully personal.

Overall, beautiful job! I can feel your excitement through your thoughtful, visceral words. You took it home for the win with the “stimulating conversations” line. Well done. 😉


New York Men's Image Consultant: Dating StyleJulie:

Your images show a nice mix of expressions which allow your potential dates to see both your serious and fun sides. To add to that, if you’re going to include two pics, I’d love for one of them to show more of your body (either full body or even just the upper half). That way, they can get a sense of your build and how you dress, and therefore determine if you’re a match physically. It also makes it more personal and less like you’re using posed headshots. This is an excellent start!


Hi there!

I like how you share your value of meaningful conversations and discovering new places. It goes harmoniously with your expat detail and love of adventures. Beautiful statement, “I consider myself an energetic person with a stable character.”

I can see your character shining through in that very statement! That’s not something you hear often – the combination of those traits — so it’s fresh and sincere.

I’d replace the, “Some people would say they don’t understand my sense of humor,” with, “It takes a special jewel of a person to really, fully understand my sense of humor — most likely, a jewel with a deep sense of humor herself who I’d immensely enjoy getting to discover!”

This way, you’re acknowledging her, calling her special, and generously / rightfully sharing the attention with her and her sense of humor.

In the food and books section, talk about your very favorite Mediterranean dish and your very favorite Asian dish. The sensual specificity of the exact meals shows your own sensuality, that you experience the world in a delicious way — implying that you’ll delight in her sensually as well, and she in you. It brings the conversation there in a subtle way. (Thanks to my friend and colleague Adam Gilad for that special tip as well as the principles of a lot of the advice I’m sharing!)

Overall, your personality shines through, and what I suggest is bringing her in more and sharing your sensual side more through describing food and places you enjoy.


New York Men's Image Consultant: Style Advice for Dating


I love the friendly, engaging smile you have in your profile pic. It makes you come across as easygoing and happy with lots of positive energy. I do have a few suggestions which will help make your images even better:

1) I like your breezy haircut, but it would be great if you could trim the hair over your ears (or have your hairdresser do it). This will clean up the look and make you look a little less shaggy.

2) It’s a bit hard to tell because the image size is so small, but I’d love for you to consider whitening up your teeth. You have a wonderful smile, and this would freshen it up even more. Crest Whitestrips are a great, affordable option.
Overall, like I said, you come across as very appealing. And with a few tweaks, you’ll be even more so.


Hi, your profile is great. We worked on it together, and when you first sent it to me, it was a little too strong with, “We are going to do xyz,” instead of, “Let’s see about xyz,” which is a more laid-back feel.

For everyone else reading, I’ll share what you and I did with your profile so they can benefit too. 🙂

First, you open with the, “You’re the kind of woman who…” frame, which sparks her intrigue and pre-qualifies. The women who respond to, “You’re usually shy, but bubbly and talkative around people who ‘get’ you,” are women who are right down your alley, from Sentence #1.

Then you continue to explore her personality, views on life, and values in that first paragraph, allowing her to see herself there.

In the second and third paragraphs, you talk about the two of you together on a fun date, piquing her interest further and showing your playful side.

Then you mention you as a couple, “if we’re fortunate to get that far with each other,” which acknowledges that you are two people with your own choices and preferences and may or may not be the right fit. This is realistic and the opposite of needy. It sets a strong vibe.

Finally, you transition into, “As for me,” and share more about yourself – both your personality and your values so she can really get a sense of you. I remember we changed one sentence in that last paragraph from details all about your multiplayer tactics game “‘baby’ project” and replaced it with, “I’ll spare you the details, but just know – it’s quite exciting though a potentially distant second to sharing a laugh with you. :)”

I love that sentence! It shares your real, palpable passion for what you’re creating while also giving her “potential” space to come in and share a laugh with you, bond with you, and be the center of your attention for an evening.

So good! All in all, you share what she’s like, what you’re like together, and then what you yourself are like, all in a way that showcases your unique personality in an inviting, laid-back, genuine way.

Well done! 🙂


For more information on Sarah, including how she might be able to help you, click over to her website Introverted Alpha.






And the Winners Are [LinkedIn Profile Pic Reviews]

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In July, I made an offer that as a free gift, I would evaluate five of my newsletter subscribers’ LinkedIn profile pics. I chose randomly from the applicants to give suggestions on where they can make improvements.  These guys were brave, agreeing to be critiqued in public like this! (I warned them that they needed to be thick-skinned to apply.) Huge props to the guys who did. See below for the 5 reviews. And if you aren’t on my newsletter list, definitely check it out, as I make offers like this frequently.

Men's Style Makeover

Fran, you have an open facial expression, which is very appealing. Busy backgrounds are usually not a good idea, but the trees in your picture mesh together, and your face pops against them so we don’t lose you in the background. Given your profession as a chaplain, these elements of openness are a bonus. The main thing I’d change about your picture is that I’d much rather see you in a button-up shirt or even a nice sweater than a plain t-shirt. Simply put, it’s more professional. There’s also something about the way your face is skewed to the diagonal that makes my brain hurt a little! The shot would be better if it was straight on so people don’t have to tilt their heads to look at you.


Men's Style Makeover

Hi Terry, thanks for the nice note you included in your entry. Here’s what I think you can improve upon with your profile pic — overall, the image feels dated to me with that colorful mottled background. For a studio shot, you’re better off with plain white behind you instead. If you’re going to redo these, I’d also suggest you get (and use) a higher resolution image so it doesn’t look as fuzzy on screen, and when you crop it before uploading, I want to see more of what you’re wearing on top. I like to think of a suit, shirt and tie as a portrait themselves, and it’s distracting that we only catch the top part of your tie. Try to show more to waist level or the bottom of your breastbone, and make sure you’re centered in the image when you crop it too. You’re smart to be wearing a solid shirt (solids photograph easily), but white can look stark in pictures, so I’d suggest a different solid like light blue instead. In terms of the content of the image (aka you!), I know it’s hard if you aren’t comfortable being photographed, but it would be great if you could give more of a natural smile. A good photographer will be able to help you relax and be more yourself in the moment during the shoot.


Men's Style Makeover

Hey Rob, your image is another where my eye immediately gets distracted by the background. You get lost in front of the tree, lights, snow, decorations, and pine cones — that’s a lot of stuff going on behind you that isn’t related to your work! It’s cool to take your pic outside or look for an interesting background, but it should be neutral and not distracting. My advice: keep it professional and get the seasonal stuff out of there. Check out point #4 in this post on how to get good headshot photos, and also this portfolio of client images on my website for ideas on better backgrounds. Your outfit, too, is a little casual for a LinkedIn shot (definitely looks like this is a pic that was taken socially but that you’re using for business). I’d suggest the same shirt with a sportcoat or suit jacket instead. Otherwise, your smile is fantastic — you come across as very personable and likeable, a can-do guy!


Men's Style Makeover

Chris, I love how you come across in this image as having a fun, upbeat personality. Who wouldn’t want to work with someone with that energy?! With your sales job, being magnetic in that way is key. A few things for you — see if you can crop the image so that the top of your hair doesn’t get cut off and so that we can see more of your upper body. Cut it to mid-chest at least. That said, the shirt you’re wearing is too busy for a headshot (which may be why you cropped it so much!). Busy patterns are distracting to the viewer. So, eventually, you should look to have a new pic taken wearing a solid color or less busy pattern instead. Finally, there is nothing like a gleaming white smile, especially if you’re selling things. Check out some of those tooth whitening toothpastes or Crest whitestrips and/or, if you know someone who’s good with photoshop, you can have him or her whiten your teeth couple shades. It’ll brighten you up and make you even more appealing!


Men's Style Makeover

Calvin, you clearly put time and energy into this shot, and it shows. I like how you’re looking off to the side — it’s different from the standard straight-on shot, and with your line of work being creative, it’s compelling. The first thing my eye is drawn to though is a dark line that cuts across the top of your image, skirting your hairline. Can your photographer edit that out? It would make a huge difference. I’m also not wild about the grey suit against the grey background, as it gets a little lost, but the windowpane pattern on your suit does make it stand out somewhat. Like I said, you clearly put effort into creating this shot, and a lot of things about it work — the patterns in your suit and tie are the right scale for a headshot (i.e., not too small). The charcoal grey suit picks up on the grey in your hair, and your skin pops against your vibrant blue shirt. In terms of your outfit, the two things I would change are your pocket square and lapel pin. The pocket square is too close to your shirt color but not exact — it looks like you were trying to match it but didn’t quite execute. Rather than matching your pocket square to a major element in your look (i.e., your shirt), you’re better off with a square in a color that picks up on a minor color elsewhere in the outfit. A light grey like the one in the pattern of your tie or the windowpane of your suit jacket would be better — it will be a more nuanced look. You might even be able to have the color of your square photoshopped so you don’t have to reshoot. Finally, the lapel pin. It’s a great detail for in-person, and it suits you and the creative image you’re putting out there, but it doesn’t translate in pictures. To someone who doesn’t know what a lapel pin is, it will be confusing and distracting (it almost looks a little like a microphone!). It’s a nice touch, and it suits you, so save it for in-person appearances.

Thank you so much to everyone who entered. You guys are awesomely bold putting yourselves out there for critique like this — I know it isn’t easy! I’ll be doing more contests like this in the future, so if this sort of thing interests you, make sure to sign up for my list so you can find out about it.



The only swimsuit style you need

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Men's Style Advice: Swimwear

Summer is over halfway through — how strong is your swimsuit game? If you’re feeling iffy about it, I highly recommend you try a swim short with a side waist adjusters. It might just change your life — or at least make you feel like a stud when you hit the beach or pool. Below are 3 big reasons why this style swim short is so flattering:

1) Flat waistbands — have you ever noticed that a swimsuit with a bunchy waistband makes you look bunchy? That’s no bueno. A waistband that lies flat against your stomach, however, reduces excess fabric which can make you look bulky around the waist. The net net is that the flat waistband you get on a swimsuit with side adjusters can actually make your stomach look flatter.

2) Pool panache — just as they do with dress pants, side adjusters convey a class and sharpness in a way those ballooning board shorts can’t dream of. And of course you can tighten or loosen them for the perfect fit.

3) Après-swim friendly — because these have such a smart, tailored look, all you need to do at the end of a successful beach day is throw on a trim-fitting polo, and you can head straight to the beach club for drinks and hors d’oeuvres.

I like the brands Orlebar Brown (one of my go-to’s for clients), along with Frescobol Carioca and Robinson Les Bains for this style.

Now obviously you’ll need to adjust the length of the legs based on your body type and comfort level, but I will say that I’ve tried this style swimsuit with personal styling clients of all different shapes and sizes, and they’ve only ever given rave reviews.

So are you convinced? Let me know why or why not in the comments below.



What to Wear to Your Office Holiday Party

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Your office holiday party. One of the trickiest sartorial events you may encounter.

You basically have 3 choices:

1) Be the boring guy who makes no effort and simply wears the same kind of thing he wears to work every other day of the year.
2) Be that guy who goes way overboard with a singing santa tie and matching socks.
3) Put in just the right amount of effort where actually come off as being effortless with your style.

No big shock, my choice for you would be #3. Here’s how to pull off an effortlessly cool holiday party look:

1) Start with your everyday office attire, then take that up a notch. So if everyday is:

  • jeans and t-shirt –> wear chinos and a nicer t-shirt, henley or polo (in this case your office is super casual, so make sure that wherever your party is taking place is not fancy; if it is, opt for one of the options below based on whatever you can find out about the venue. If you’re at all unsure, it’s always better to be overdressed for something work-related like this.)
  • chinos and a button-up shirt –> wear dress pants or chinos and a button-up, and add a sportcoat or nice cardigan/v-neck sweater
  • dress pants and a button-up shirt –> wear dress pants and a button-up, and add a sportcoat
  • dress pants and a sportcoat –> wear a suit open-collar
  • a suit and tie –> wear your sharpest, best-fitting suit and a tie that meets one of the criterion below

2) Add 1-2 tasteful, festive touches in the form of a bright color, luxe/wintery fabric, slight sheen or extra panache from the following list:

Men's Style: What to Wear to Office Holiday Partysocks

What to Wear to Your Office Christmas Party: Tietie (or bowtie, if that’s how you roll)

What to Wear to Your Office Christmas Party: Pocket Squarepocket square

Men's Style Tips: Office Christmas Partydress shirt (if you’re wearing one)

Men's Style Advice: Office Holiday Partycuff links

Men's Personal Shopper: Office Christmas Partytie bar


What are you wearing to your office holiday party this year? Let me know in the comments below!



Stay Handsome with these Head-Turning Halloween Costumes

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They say you can tell if a woman is single or attached based on how sexy her Halloween costume is. It’s a different case for men though — most guys’ Halloween costumes are super dorky and do little in service of sex appeal.

(I’m talking to you, guy-in-Dog-the-Bounty-Hunter costume who tried chatting me up last year.)

But I say why not even the playing field? There’s no need to subject yourself to such ridiculousness, and you can in fact look kinda dashing on Halloween, especially if you take it as an opportunity to show off well-fitting wardrobe items. Trust me, the ladies would much rather see a guy in a suit that fits like a glove than some plastic-y costume you picked up at a Halloween superstore or a DIY-job covered in marker scrawl.

With that in mind, here are three Halloween ideas that will have you standing out from the sea of unattractive and unflattering costumes most guys are wearing.

Men's Style Tips: Stylish Halloween Costumes1) American Psycho – Take one pinstripe suit, mix in one contrast collar shirt, a pair of braces + a red “power tie,” add a clear plastic raincoat, and what do you have? Serial killer and Manhattan businessman Patrick Bateman in “American Psycho.” Then all you have to do is slick back your hair and walk around humming Huey Lewis tunes (fake axe optional), and you’ll be in business.


Men's Style Tips: Stylish Halloween Costumes2) James Dean – Feel like a boss on those tight jeans? Get after it and channel your inner James Dean. Other than the jeans, the main things you’ll need are a slim-fitting t-shirt (here’s my primer on how this should fit) and a dark well-fitting bomber jacket or black leather jacket (here’s an oldie-but-goodie that explains how to find the latter). Final touches: unzip that jacket just enough to look mysterious, and of course you’ll also want to do your ‘do.

This one’s not exactly family-friendly, so use your discretion if kids are around.

Men's Style Tips: Stylish Halloween Costumes

3) Chippendale – If your tuxedo fits you well, it’s actually one of the most flattering things a guy can wear. Why not bust it out (or at least parts of it) in a tongue-in-cheek way and dress like a Chippendale à la Chris Farley and Patrick Swayze above. Wear the pants, the bowtie, and grab yourself a collar and cuffs set.

Men's Style Tips: Stylish Halloween CostumesWhat are you wearing this Halloween? Leave me a comment below or post a picture on my Facebook page.



Want Your Style Questions Answered LIVE?

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Men's Style Tips

Got a question for me? I’ll be taking questions LIVE On my free online event: “How to Dress for Power & Success” next week.

Men's Style Advice

Click HERE to claim your spot for one of the two times I’m offering. I look forward to seeing you there!

That’s What She Said, Vol. 3: Nisha Moodley on How to Be a Man That Makes It Happen

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In my third and final interview, Leadership Coach Nisha Moodley explains how attractive “a man that can make it happen” is to her, and how having good style can easily create that. She also gives her take on the difference between confidence and cockiness. Click here or on the image below to hear what Nisha has to say on the matter.

Men's Style Advice: What Women Like

And if you’d like more style tips and to get your questions answered by me, sign up for my FREE online event “How to Dress for Power and Success” coming up next week.

That’s What She Said, Vol. 1: Sara Davidson on Dressing for Attraction

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I interviewed some of my most successful, smart, and gorgeous girlfriends to find out how important it really is to them for a guy to pay attention to his image and style, and I thought you might be interested in watching what they had to say. The first of these three interviews is with Sara Davidson, business strategist and marketing maven.

Click here or on the image below to watch our interview. You’ll hear what turns her on and off, and the one thing a guy did that completely changed the way she looked at him (and as a result she couldn’t keep her hands off of him).

Men's Style for Dating

After you’re done watching the interview, make sure you take my style quiz to see how you rate on a scale of 1 to 10.


How Powerfully Are You Showing Up?

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Have you ever wondered how you rate on a scale of 1-10? Fall is practically here, and the holidays right after that. Those are key times to be exuding confidence and looking your best.

If you want to get serious about your style, and be taken seriously as a result, I invite you to watch the video I made for you explaining how it all works. I’ve worked with hundreds of men worldwide, and it’s been my incredible privilege to observe how much their lives improve and what opportunities come their way when they upgrade their style.

On the same page as the video, you can also take my style quiz. It will show you how you measure up, and what you can do to get to a 10.