Golden Rules:
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For many women, a bad pair of shoes can spoil a guy's entire outfit. So like it or not, you're going to have to a) own more than one kind of shoe, and b), match your shoes to your entire outfit. Fortunately, matching your shoes to your outfit is easy. Follow these rules:
- For casual wear, go with loafers or skater sneakers
- For clubbing, stick to loafers or dress shoes
- For a formal occasion, wear dress shoes
- For shorts, wear sandals or flip flops
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A Nerd classic. Sure, it's nice to give those feet a little extra warmth, but let me tell you:
there are very few things women hate more than this footwear choice, especially
if your sock choice is a pair of blinding-white tube socks! Ask any woman in the world - to them, wearing socks with sandals is an extremely heinous act.
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Yes, as a kid you wore the same pair of running shoes for just about everything. As an adult, that just doesn't cut it any more. Unless you're doing some running, no running shoes. Period. Sometimes you can pull off stylish basketball shoes and jeans, but to be on the safe side keep any athletic shoes you own for the gym only (besides skater sneakers.)
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If you're wearing very small socks that do not show outside of your shoes, then it doesn't matter what color they are. However, most male socks DO show above the shoes, so listen up!
Gleaming, bright-white socks, worn beneath jet-black dress shoes - do you see a problem here??? For some reason the white athletic sock seems to be firmly entrenched in North America, but it's time for it to be banished to the locker room! You want your socks to complement your shoes and pants - not stand out on their own! Also, you'll want to keep your sock-length on the shorter side, unless you're a 1970's NBA basketball player. One last thing... again, never, EVER, wear white socks with dress shoes.
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Rule methodology found here. Click each
to expand details.
Items to Avoid:

Running shoes (unless at gym)
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Velcro
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Bright
flip-flops
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Moon boots
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Platform
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Standard "Can't-Go-Wrong"
Suggestions:
Please note: the shoes listed below are example models. We're not advocating any exact make or model of shoe. Each shoe is linked to a vendor offering free shipping and free return shipping - a must if you're going to order shoes online. The 3 vendors are:
Men's Loafers |
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| A staple of the office, there's not too much to say about these shoes. Any shade of black or brown is fine. You'll be wearing these around work (so go for comfort) or on more casual dates - so nothing too flashy is required i.e. not too pointy, and no fancy buckles. |
Men's Skater Sneakers
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| These are the only running-shoe like footwear you can get away with in non-athletic circumstances. Best to wear these only with jeans or chords - too informal for khakis. Some clubs have a no-sneaker policy so be wary of wearing these for a night on the town. |
Men's Sandals & Flip Flops
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If you're going to be wearing shorts, it is mandatory you get yourself a pair of these. Nothing else looks quite right. But for the third time, don't wear these with socks!!! One thing to keep in mind - if you're going to wear sandals, you've got to make sure your toe nails are clean.
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Men's Dress Shoes
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Kenneth Cole Reaction - Men's Stock Split

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Without this essential item you are doomed to be unfashionable at a variety of important events. Make sure you have some black socks to go with them. Although it is necessary to have a pair of dress shoes, don't wear them with your more casual outfits. Take a pass on shoes with heels greater than one-half of an inch. |
Advanced Options:
- Make sure you wear socks with your shoes (preferably dark in color)
- Winter boots (leather) should come to just above the ankle. No platforms
- Some women prefer belt color to match shoe color
"Whenever I'm sitting somewhere, I look at guy's shoes."
Gloria, 26, Ph.D. Student
"Try not to buy your shoes from a store with 'Mart' in the name"
Andrea, 27, Teacher