Molly Bloom knows style

My Indianapolis Colts are playing in the Superbowl. I call them mine because Indy is my hometown. I went to the first Colts game in the Hoosier Dome and season after season I attended Sunday games. They were a crap team the entire time I lived in Indiana. Now they’re in the championship and I have decided to be a fair-weather fan. Everyone loves a winner.

Those of you who think I’m uptight about the rules of fashion should know I have come to accept the team jersey, insignia hats and such. Not all together at the same time. Unless you are painting yourself blue and white in man makeup, in which case I want to see that hideous oversized foam cowboy hat.

The key to chic spectatorship is to dress like a fan not an athlete. No need to wear those go-fast gym shoes with jeans and a jersey because you won’t really be running around the couch to the buffet table. You don’t need the gym shoes. You are the couch quarterback. Consider lace-ups or Campers or something.

Now for the pants. Do take care to select the appropriate color. If you’re wearing a blue Colts jersey you can’t just put on any pair of jeans. Jeans do not match everything. Medium or light jeans could be clash-a-rama (actually, take a time-out and throw away the light-wash jeans or I may have to get out the penalty flag). Dark indigo denim could look sharp, ditto black. Personally I like a little preppy with my sporty, like some flat-front trousers or cords.

So you’ve got your $200 NFL jersey on top. I see men wearing these enormous jerseys and this makes me sad. Wearing giant jerseys makes you look deflated and puffy at the same time. It doesn’t have to be skin tight but the short sleeves should not be hanging past your elbows. It took me a long time to accept the team jersey and I just can’t budge on this final point.

I do like the antiqued sports jerseys a la Blue Marlin but those are old news. There is a balance to strike between team spirit and debonair. Personally I wish football players still looked like those old Ivy League team pictures from the 1930s, back when men were men and they played football in a sweater and leather helmet. Which would also be an acceptable Superbowl Sunday look.

1. It’s cold outside. Scarves will beat back that mean wind or make up for not wearing enough layers. A scarf will winterize your raincoat.

2. It’s cold inside. Scarves indoors are cool awesome. You can keep a scarf at your desk for when it’s arctic in your cube. You can wear a scarf with your jammies when you’re curled up on the couch. Scarves are cozy.

3. Scarves are jaunty, says Ted — wear them easy, not too fussy. I agree.

4. If someone knits you a scarf you are lucky. You have to wear it.

5. You’re in an indie rock band. This one’s kind of weird because it looks hot under those stage lights. The style jury’s kind of out on this one but it does seem that a precedent has been set.

You probably surmised that this column is about making some fashion resolutions. That’s why I love my dear readers, such smarty-pants! So handsome!

Fashion rule numero uno: If you haven’t worn it in a year, get rid of it. Exemptions are given for special occasion items such as tuxedos or clown suits. But those pleated, faded navy blue Dockers? Goodbye. That belt you haven’t worn since college because it seems to have gotten smaller or something? Off with its head.

Throw away half of your T-shirts. Throw away most of your T-shirts. Even if they’re in fine condition, get rid of some. That never-been-worn bright blue T-shirt from a conference sponsor is going to reman that never-worn bright blue shirt. Free up some space in your chifforobe and fight temptation to wear really bad fashion, all in one sweep. And don’t give me that “I’ll wear it to the gym” crap. You don’t need 80 bad T-shirts to wear to the gym. I cut old T-shirts into cleaning and dusting rags.

Get rid of worn-out shoes. If they smell they’re always going to smell and if they’re past the point of repair you have no business wearing them. Think of the poor toesies. And for the love of all, throw away those Doc Martens shoes. They haven’t been in fashion for a decade. A lot of men still have these in rotation, including my dear husband who is going to be annoyed about this, and while I admire a well-made shoe I call bullshit on the yellow stitching and 1990s shape of Docs. I was going to make a joke about Pearl Jam and goatees and Lollapalooza but that seems cliched. Like Docs. Ahem.

You know how I’m forever going on and on about buying quality clothes and making an investment? Now is the time. It’s clearance o’clock out there. Every man — yes, you — should own shoes like these lace-up Oxford puppies that are on sale for $79 (with $5 shipping). They’re classic, handsome, manly and always in style.

Take a look in your sock drawer. Get rid of orphans. Get rid of faded, shapeless, holey socks. Get rid of those nylon ones you bought at Walgreens so you could put off laundry for a while — you know they make your feet reek. Pick up some wicking athletic ones for sporty times, some medium-weight socks in brown, black or (oooh!) colors for everyday casual wear. And get a few nice pairs for dress-up, promise?

Donate your old eyeglasses and sunglasses. You won’t need those owl-ish tortoise shell frames ever again. Send them to this San Francisco address. What a rad tax deduction.

Hey hipsters: indie purveyor guyshop.com is having a sale. Go get trendy.

Resort wear is the umbrella drink of the fashion world. It should be fun, colorful and a tad sweet. You wouldn’t order a Blue Hawaiian in a Manhattan wine bar. Nor should you wear grays, dark colors or muted prints in Tahiti.

Men’s resort wear is best when cut in classic styles from whimsical, preppy and occasionally loud fabric. The classic lines are important as they keep you from looking like a Day-Glo clad Daytona Beach tourist. The color is important because it keeps you from looking stodgy.

I love the wacky, bright preppy summer clothes of the 1970s. Think vintage Lilly Pulitzer. Or new Lilly Pulitzer. I also like to see a man in seersucker or madras patchworck pants.

I’m not a big fan of shorts. But since most men don’t have the option of wearing a skirt or dress, I’ll give a pass. Beach vacations are exactly where you should be wearing shorts. Pack at least one nice pair. You’ll have room for them in your suitcase once you throw away those jeans shorts, because there is never a time when jean shorts are right. I am an absolute believer that it is possible to wear the right shorts with a shirt and tie, soft loafers sans socks. Really. Meow.

Try on shorts of different lengths. That lingering trend from the 1990s of wearing really long shorts makes most men look as if they have extremely long torsos and short midget legs. This goes for swim trunks as well, the too-long swim suit being the least sexy thing I personally can think of seeing on a toned body. Boo.

Don’t rely too heavily on T-shirts. Boring. Instead pack a few light-colored dress shirts to pair with shorts. This is an easy look for even the most fashion illiterate. Roll the sleeves up to the elbows or wear them unbuttoned with swim trunks.

A lot of men wear golf shirts for dressier resort occasions. I don’t like golf shirts but I recognize their place in the canon of men’s fashion, so I won’t say any more. Except to say that horizontal stripes, especially on a knit fabric, will make you look chubby.

Be sure to grab a tropical tie. And some nice sunglasses. And a summery, lightweight belt.

Ooooh, one last thing: I suggest a banana daiquiri.

So your mom asked what she could get you for Christmas and you said you don’t know. Gentlemen, this is the perfect time to score those items you need but aren’t willing to throw down on. Your mama loves it when you dress up. Just look at how handsome you are!

Why not add a black blazer to the list? This two-button velvet number is perfect for the holidays (think mistletoe and New Years kisses, Mr. Fancy). Velvet isn’t for the office but you wear jeans there anyway. If cocktails are served and there’s a chill in the air, this jacket is the way to go. Pair it with black-black dress pants, the kind you have to take to the dry cleaner. H-O-T.

You need a nice tie. A really nice tie. That cornflower blue tie you’ve been wearing is boring us all. We won’t even mention the novelty tie, the one with the cartoon characters. Time to kick it up a notch, guys. These ties from Paul Smith are punchy but not cutesy.

A nice crisp white shirt is sexy. It will work with that black blazer or maybe your new tie. It’s the kind of thing that separates the men from the boys, even with jeans and black oxford kicks. Ted Baker makes killer shirts that get extra points for use of cufflinks and his ties are great as well.

Cufflinks! You should get some. Your date will notice. That hottie across the room will notice. Get some nice sterling silver ones or maybe something with a nice inlay. If you wore cufflinks every day you’d get laid more often. Trust me, I know these things.

If your mom is rich and you don’t lose things, this cashmere peacoat is so very handsome. These Gucci loafers are outstanding. Rawr.

The anecdote about “and all I got for Christmas was socks!” wouldn’t suck so bad if they were cashmere socks. And these cashmere-lined leather gloves aren’t so bad either.

If you’re still slinging on a backpack when you fly home, it’s time for an upgrade. The Spinner series from Samsonite is well-built and features multidirectional wheels that make it easy to maneuver down airplane aisles.

Your mother wants to make you happy. Send her links or photos so she’ll know exactly what you want. What you consider a cashmere sweater may not be what she has in mind. And be sure to send her your measurements. If you’re not comfortable having mom pick out your date clothes, ask for a gift certificate. But you gotta actually use it for cool stuff, promise?

I don’t know where you live but San Francisco has had a couple of gullywashers in recent weeks. As promised, here are some stylish raincoat options to keep the menfolk dry.

A simple, well-cut single-breasted raincoat will be in style for years. This black raincoat from British purveyors Racing Green is ideal.You could wear it as an overcoat atop your suit (as pictured in the catalog) or as an everyday piece. It’s lined so you won’t freeze your tuchas off.

A more casual option is the Sutherland trench from J.Crew. This coat is date-worthy and weekday appropriate. It has an interior pocket for your MP3 player. It doesn’t seem to have a super-warm lining but if you live in the Bay Area you’re wearing layers anyway and should be fine.

One warmer option is a raincoat with a zip-out lining. If it’s cold, zip it in; if it’s too warm zip it out. This convertible number from JOE is a good bet.

There are always trenchcoats to keep you dry. I especially like the below-the-hip kind which seem less stodgy than the longer version. All the raincoats I featured here fall past the hips which will keep you dryer even if it’s just a wet bus seat you sat on. No one likes wet buns.

I’m also a fan of umbrellas that fit in a pocket. You can keep one in your pocket and forget about it until you step outside and need one. Totes has been making sturdy mini-umbrellas for years and H&M stocks $7 versions at the checkout counter.

Recently someone asked Ted to ask me where they could buy a purse for their girlfriend.

Can I just say that buying accessories for other people is tough business? Dudes are dudes and probably don’t realize there are a million kinds of purses and that women are pretty specific about the kind they carry. You may want to buy her a special handbag, one for weddings and New Year’s Eve, one that will make her feel special. You may want to buy her something she’ll carry every day as a reminder of your love (aww, cute!). Buying purses is not an impossibility. Ladies love gifts so let’s make it happen.

One obvious question is: What kind of purse does she carry now? Some women carry the same purse every day until it falls off its strap or has some sort of blowout. I carry the same bag most of the time, a kicky orange Marc Jacobs number that Ted gave me (that I picked it out, caveat lector). Sometimes I carry a sporty black purse from REI that is vaguely stylish but most awesome for traveling (big enough for a map of Shanghai, camera, travel guide and wallet) or events where it would be stupid to tote around luxury leather goods. Add in the dozens of special occasion handbags and clutches I own and I can see I’ve lost you already. Like I said, purses are tricky.

If I were a professional shopper and I were buying this gift, I’d ask if her everyday purse is a shoulder bag or a handbag. I’d also want to know what kind of shoes she wears most days (dressy? casual? heels? flats? boots? trainers?) and what color her overcoats are. If you buy her a brown leather purse but she wears a black leather jacket most days, that’s a mismatch. I also don’t think you should buy the most basic thing in the store; purses are a peak into a woman’s personality. A handbag completes a look and shouldn’t be a scene-stealer or the dressiest part of an outfit.

One way to find out just what she wants: drop hints. Find out who her fashion idols are, ask about her favorite brands and colors, and inform the sales staff. You could even try the guy standby, “Not to be gay or anything but that’s kind of a hot purse” as you flip through the Sunday Times together.

Perhaps a gift certificate with explicit instructions to buy a purse is the way to go (extra points if you tuck the gift certificate into a child’s purse or cut out a few purses from magazines). Maybe you could go shopping with her. Who doesn’t love a surprise shopping spree? Nordstrom has a solid purse department and helpful staff. So does Bloomingdale’s although their price points may be a little higher. I’m a huge fan of leather purveyors Lava 9 on Hayes Street in San Francisco. Another indie option is Hayden-Harnett out of Brooklyn — check their online store. Purses can be expensive, so do some research and set your max price.

What’s the one thing you wear every day and don’t consider often enough? Your jacket.

Too many people put too little thought into jackets and coats. Unless you live in a place where it is always warm, you should have a jacket for every season and every occasion. Outerwear is the first thing people will see; why own just one?

If you want bad service at an upscale restaurant, wear your Patagonia. I know it keeps you dry or warm or has a handy loop for your fishing license. But it is not a stylish garment. It distracts from anything cool you might be wearing. These jackets are best left for Desolation Wilderness or picking up a pizza during a monsoon, not a Fischerspooner show at the Fillmore (true story).

There are a lot of cool jackets out there. James Dean’s sleek red windbreaker is one iconic look worth copying, weather permitting. There are a lot of good vintage looks, but I’m growing skeptical of resale shops — at this point all the good stuff from the 1960s and ’70s has been sold, worn and sold again. The stuff is either worn out or embedded with someone’s b.o.

Once the weather turns chilly, a pea coat is a classic pick (see pic above). They work on most body types, and seriously — what do you have against navy blue (or the twist-on-a-classic black)? Nothing, I hope. Pea coats can be casual to kind-of dressy, great for everyday or dates.

Leather jackets are perfect for windy, blustery San Francisco. I’m not a big fan of the bomber jacket because I think they’re a bit tired and the elastic at the waist adds pounds around the middle. I prefer the slim shape of the faux motorcross style jackets or simple plain-front models. Some leathers have Thinsulate or other thermal lining. If you’re shopping for a raincoat you may find them too unsubstantial without such a lining unless you’re really into sweaters.

I’ve never met a shearling coat that I liked. I’m not sure exactly what but there is something unchic and lumpy about shearling. It’s a look that seems to endure in men’s outwear, so prove me wrong if you can.

I know I say this a lot, but don’t be cheap with something you’re going to wear every day. A good leather jacket will last for years and you can have it refurbished (re-dyed in light spots, new buttons sewn on, etc.) for about $50. A nice raincoat is practicaland chic. I have had some of my jackets and coats for years, bringing their price per wear (or price per season) down to nothing.

UPDATE: Next week’s Guy Friday will be all about raincoats. Thanks for dialing the request line, Ted.

There are topics in life that are more interesting than underthings. Perhaps that is why so many dudes let their drawers languish, nary a thought as to how they might look when undressed to reveal… snowflake boxer shorts with snow men printed all over them?

Boxer shorts aren’t as sexy as they used to be, back when your first stopped wearing those Fruit Of The Looms your mama bought you. Back then anything other than tightie whities seemed hot. But there’s a lot more out there than plaid boxers and white briefs.

Briefs are kind of good, don’t you think? There’s nothing wrong with black briefs, unless they’re stretched out or fraying or otherwise tore up. Do not even entertain the thought of white briefs (you know why). General rule: if the name printed on the waistband is stretched to a funny font, it’s time to go up a size or go on a diet.

A slightly more modern choice is boxer briefs, which employ the tightness of the brief and the length of a boxer. They are a fine choice if you’re of taller, long-legged stature. Otherwise they seem too modest and remind me of a man-girdle.

Trunks are short-legged and tight but not briefs. They are a straight-girl favorite (based on a non-scientific poll I conducted). You can’t go wrong here.

Boxer shorts do seem to work well on fuller figured guys who might like to be a bit covered up. And maybe you are just a boxers sort of guy, and that’s fine too. If you insist on wearing holiday boxer shorts, please pack them away with the jack-o-lanterns or tree ornaments so they are only worn at the appropriate time of year. And those Valentine boxer shorts from an old flame? Throw them away. Nothing says “gift from my ex” quite like novelty underwear.

brogue - A heavy, oxford-style shoe featuring pinked and perforated detailing. Many golf shoes are brogue in design.

Some stylish brogues for fall: Affordable and casual Fluevog (shown above), gorgeous Italian oxfords and luxe luxe luxury.