‘What to Wear’: 4 Seasons of Dating Ms. Breanna Hughes

Guest Contributor: Jonathan Elias of ShopMyClothes.com

I had the pleasure of meeting the talented Breanna Hughes at the FORA MTV launch party a couple of weeks back.  A self professed tech nerd, board game enthusiast and serial dater I decided to delve further into the person known as ‘Unbrelievable’.

So we got to talking and decided to join forces on a venture of educating the male population on what they should wear should they decide to ask Ms. Hughes out on a date.  Now while this may seem as a simple task, I assure you it is not.  We are dealing with a complicated, beautiful, talented and very intelligent women who while denounces the world of fashion, secretly loves it; as professed by her affection for Jeffrey Campbell shoes.

So with that… lets get started.


As spring approaches it was only fitting we start here.  Since its still a little cold lets make sure we dress appropriately.  Throw on that plain oxford button down, don’t tuck it in you don’t want to seem too uptight. Next, find a nice pair of well fitted jeans, no they don’t have to be painted on but make sure they are not baggy and that they sit on your waist; remember, we’re not 19 anymore.  Now comes the hard part: the shoes.  She’s a picky one so this is important.  I recommend a pair of desert boots of the tan variety.  You can’t go wrong with J. Crew or Red Wing.


It’s time to move on to the summer portion of our date.  This is probably the easiest to put together.  She likes confident and laid back with a little bit of style.  Throw on that white v-neck tee, roll up those slim fitting chinos (no further than the calf) and slap on some boat shoes and you’re ready to go (socks not necessary).   I recommend you arrive on your bike.


As we hit fall, a plaid shirt is a must at this time of the season.  A pair of cords with a slightly rolled cuff so she can see those argyle socks you have on and, to top it off, a pair of brown leather Ranger Mocs (I recommend L.L. Bean’s signature line, a very inexpensive alternative).  And if you’re feeling ‘adventurous’ maybe an outerwear piece such as a vest or thick sweater.  Nothing oversized, something that is slim to the body (This of course can be optional).  It will add that little extra bit of ruggedness to the look that I know she will appreciate.

As I put the last outfit together I wonder to myself how many hearts ‘Unbrelievable’ has broken.  If you follow these first date fashion tips I can assure you will at least last to the second date, I just can’t guarantee another season.


I’m all about the layers at this time of year.  A button down oxford or an unassuming plaid shirt is where we would begin.  A nice houndstooth blazer, I’m not talking about a King, Bay or Wall street looking one, something with a little bit more style and not so formal.  Have a look at the Engineered Garments Baker jacket, which in my mind would be perfect (a bow tie is optional).  Again with the denim and a slightly rolled cuff but this time we’re going to throw on a nice pair of winter boots, something very minimal and NOT chunky.  I recommend a light brown or black that lines up right above the ankle.  As you are about to head out the door, throw on that navy newport jacket and red or grey toque and you’ve finished the outfit.

Now while I can’t guarantee a good date, I will guarantee a fantastic first impression.  The rest is up to you and that, boys, is easier said than done.  If you’re lucky enough to get a first date with Ms. ‘Unbrelievable’ you’re doing something right.  So good luck, follow the fashion tips and don’t make her wait in the rain!


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If you liked the above suggestions, read the ShopMyClothes Blog for great fashion tips and tricks, for both guys and girls alike. You can also follow them on Twitter, or become a fan on Facebook.

Interested in doing a collaboration with me? Contact me with your cool idea (or I’ll help you think of one): me at unbrelievable.com.

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  • john

    Basically be a hipster! lol

  • http://www.unbrelievable.com/ Breanna Hughes


  • john

    Sweet! Im so in there. haha

  • jhoo04

    I would say more of a 'high end' hipster. Not that that's a bad thing!

  • mayamoose

    edits for summer:

    “slim fitting chinos (no further than the calf)” ???? – I would love for you to date a guy wearing tight khaki capris!!!!

    should read: baggy army green shorts

    please no slim calf length chinos

    or he may have an uphill battle winning me over……and mike……unless he has thick skin…..

  • http://twitter.com/patbateman_ Pat

    Hmmm I think you're recommending dating a gay dude.

  • http://www.unbrelievable.com/ Breanna Hughes

    Well Jonathan is not gay, just has great style.
    I've fully embraced the “metrosexual” aspect to males, and that just because they are guys, doesn't mean they have to dress poorly.

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