And you only have a couple seconds to show you’ve got them on!

Why a couple seconds?  That’s how long it takes to make a first impression. Sounds scary but there’s no need to fear.  Let me show you how easy it can be! 🙂

Let’s start with my guess that your your first date is not likely to be dinner in a fancy restaurant, nor a trek into the woods, shall we say lunch, or an upscale coffee shop or a classy bar – outdoor seating these days (what the heck are we all going to do in December!?).

So the setting is “smart-casual” to paraphrase.  This might easily lead you astray.  I mean, if you were meeting your buddies at the same location you could easily show up in:

  1. The trousers and the uninspired solid blue shirt you wore to the office earlier that day
  2. What you were wearing running errands earlier – Saturday jeans and a clean band t-shirt
  3. If it’s hot- cargo shorts, flip flops and a polo

So my Gentlemen friends, you can do SO much better by heading toward these 5 apparel choices:

  1.  She loves boots.  Boots are masculine.  They look great with jeans or casual pants. Boots can be soft structured like suede chukkas, or more substantial leather.  Unless you are looking to inspire a motorcycle riding partner or a mountaineering buff, keep your boot profile on the lower side, not heavy soled and bulky.  Think streamlined.  If the weather is not boot friendly (too hot), refer to my article on Men’s Sandals.

2.  She expects a shirt with a collar. If you follow this, you’ll get a check mark for having tried, no matter all else.

Sidebar, when I was married and my husband and I were dressing for an event, I used to feel exasperation at our dressing-up “negotiation” dialogs.    “It’s really easy to know what to wear – If I am putting on a pair of nylons you are wearing a TIE.  If I’m putting on a dress, skirt or heels, you’re putting on a collared shirt and real shoes.  SO EASY!”  Maybe I’ll have to make a future blog post on that one…!

So anyway, a collared shirt signifies you tried and will be appreciated.  If your date setting is outside and it’s warm, a polo shirt is quite suitable.  If you are at a nice bar or inside, try opting for a button up shirt.

3.  She will appreciate pants that fit.  You think you are the only one looking at her walking off to the rest-room?  Haha, nope!  So you know I am a custom clothing expert – here’s a little insider info:  Just like in ready to wear suiting, you know the trousers are constructed to measurements that are in relation to the jacket size, right?  Well, jeans and casual pants have the same concept – called “drop”.  The drop in mens pants refers to the dimensional difference between the size of the waist and the size of the hip.  (aka butt).  The standard drop in men’s ready to wear pants is 6″.  This means when you put on a pair of 34″ pants, the hip (butt) will be sized at 40″.  This is all well and good if your body happens to fall into those parameters.  But as men age (especially white guys) the bigger their tummy gets, the more they have baggy butt or “no-ass-at-all” syndrome.  If you are wondering if you are one of the affected many, just reach around to the back and see if you can grab a handful of fabric at the base of your seat.   Ah… yup… I thought so!  Serious plug for custom fitted casual 5-pocket (jeans style) pants here from J.Hilburn. 

IMO, you can get away with ready to wear shirts on the edge of fitting well better than pants that fit marginally.

4,  She will remember if you wear something with color and pattern.  Unless your style includes madras or lobster chinos, this item is probably going to be your shirt.  Both color and pattern can create or diminish the energy you convey.  If you are a high intensity person who knows you are easier to meet for the first time if you tone it down a bit then skip the big red and black buffalo plaid and wear a more subtle color and pattern.  If you are a little shy, or on the quieter side, a fun pattern or color will add energy and vibrancy to your look.  Fun is not garish, it’s just more than Brooks Brothers Blue.   Want more?  This is what you learn in a personal consultation.

5.  Adding is third piece is your “Style Ace in the Hole”!  Adding a third piece to your wardrobe, a sweater, jacket, or vest, moves your outfit from okay to terrific.  (It separates the men from the boys!)  A third piece, even if you take it off 2 minutes into the date, like a sport-coat, demonstrates that you have a more refined sense of style, that you care about details, and you care about looking good for HER!  In the picture I choose for this article, the 4 young men are all very casually dressed, but can you see that none of them looks sloppy or like they just rolled out of their closet?  They look casual, laid back yet dressed.   I like it!


Ann Lindsay is Suited for Love and Style of Success

I work to make you look effortlessly confident. 

Image Consulting      —       Personal Styling

Concierge Shopping        —       J.Hilburn Menswear Stylist

I bring confidence, organization, efficiency to your life.

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