Biking to Work and Looking Cute: Not Mutually Exclusive

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Dear Frank,

I recently moved to a location that allows me to commute to work by walking or biking. So wonderful for many reasons, but I will admit that I miss having my car to hold all the stuff I might need during the day—and my shoes certainly don't love the mileage.

I have a standard bike messenger bag and I slap on some Converse tennis shoes for the walk/ride, but I would like to look a bit more put together and professional when I arrive at work. My office isn't super fancy, but can you recommend some bike friendly looks (one pegged leg jean anyone?) that I could adopt for the commute?

Thank you!
One-Peg McGee

Dear One-Peg,

As someone who is semi-frequently on a bike and very frequently unimpressed by the way other people on their bikes dress, I feel you.

It's tough to look pulled together while biking. If you have a helmet on your hair is ruined. If you don't have a helmet on your hair is ruined. Messenger bags can be goofy, or overly sporty, or much too big.

The one rolled up cuff looks ridiculous and I somehow always manage to get my knits or the bottoms of my jackets greased up or stuck on to something.

Could you imagine if I had long hair? Forget it.

And that actual bicycling gear—the stretchy, synthetic, super-streamlined, skin tight tops and bottoms—you know, Green Man but without the head? Well, they're not forgiving. And they certainly aren't office appropriate.

My advice: Invest in a chain guard. You can grab one at Kmart for about $20 and screw it on yourself. Or, pick up one at your local bike shop—it'll cost a bit more but they'll probably install it for you (and check your breaks and your gears and your tires while they're at it).

Of course, this is not the option for some serious bike people—a chain guard is an inconvenience while tinkering; it weighs a bike down, it's not aerodynamic; it's just not done. But for the casual biker—it's a great way to look a little less foolish while commuting or enjoying an afternoon in the esplanade.

As for bags—if you're ready for something you can strap on while biking that is chic and office appropriate—may I suggest you jump on the backpack mega-trend bandwagon.

Certainly, there are many, many backpacks that will make you look and feel like a giant third grader. But there are just as many really smart looking options at price points that run the gamut from cheeky printed canvas by Herschel Supply Co. for around $60 to ostrich and python and mink iterations by the Row that cost about as much as a starter Mercedes.

Check ASOS, Club Monaco, Madewell, Urban Outfitters, Bloomingdale's, or Need Supply Co. for one that isn't too large, isn't too sporty, has clean lines, and won't look a little silly in your office or at a wine bar after work. Something in a saddle- or oxblood-colored neutral leather would be perfect.

A true messenger also works. But for work I suggest you retire the Timbuk2 and choose something in leather or a fine, solid-colored weather-proof nylon. Kate Spade and Jack Spade are good options—so are Coach, Ralph Lauren, and, of course, Louis Vuitton. And don't forget to look in the men's department—a bag's a bag. As long as it's on the smaller side of the messenger spectrum and you're the one carrying it, well, it's a women's bag.

As for your outfits—avoid the longest and shortest skirts; maxi anything; loose, oversize knits, dusters, trenches. I mean, just don't get stuck in your bike. Or flash us. Trim trousers and cropped pants are probably a best bet. Likewise waist- or hip-length outerwear. Perhaps a weatherproof parka from J.Crew in in order; or a classic peacoat. You also might want to invest in a proper rain jacket for those wet days. Uniqlo often stocks a lightweight version with clean lines in punchy fashion colors. A boot or sensible flat will be as comfortable and a little more buttoned-up than a pair of Chucks. I suggest you treat your leather before wearing it all out, though—you'll get rained on soon enough.

Finally, definitely wear a scarf and sunglasses. Because cute.

Got a style question for Frank? Leave it in the comments or email one in here. Then buckle your two-toned leather Moschino belts, folks, because it's going to be ? Something.
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