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Stacy solves your harsh winter style issues

Have a clothing crisis this season? Wondering how to belt your sweaters or tuck  jeans into your boots? Have no fear. TODAY style contributor Stacy London tackles some of your burning fashion dilemmas.
/ Source: TODAY contributor

Have a clothing crisis? Are you style-impaired? Fashionably challenged? Unsure what trend to wear? Have no fear; TODAY style contributor Stacy London tackles some of your burning fashion dilemmas.

Q: I keep buying belts but have no idea how to wear them beyond boring through-the-belt-loop. I have tried one over a dress or sweater, but somehow it just looks wrong. Can you help? Allison, Brooklyn, N.Y.

Dear Beltless in Brooklyn, Do not despair! You, like most people, stick to what you know works when it comes to style. A belt goes in the belt loop to hold up your pants; no-brainer. But your instinct to see a belt as more than just the sum of its use-value is the right one. You can use a belt to create structure in an outfit and a more flattering body silhouette. The heavier the material (like knitwear), the closer it should sit on your natural waist or to the top of your rib cage to create an hourglass body shape, where the waist is focal and appears to be your smallest body part. 

For another great way to create or enhance a small waist, try a thick belt cinched tight over a blazer or coat for a similar effect. If, however, you carry weight in your top half (chest and/or tummy), try wearing a draped chain belt with a wider trouser at the hip to balance your bottom half with your top half and create visual balance to your entire body line.

Belted dressesGAP: $68 gray heather ruffle-neck shift dress available at GAP retail stores nationwide and
MICHAEL KORS @ BLOOMINGDALE'S: $42 red patent belt available at Bloomingdale's department stores or call (212) 729-5900
BOUTIQUE 9: $100 Raven brown suede heels available at select Nine West Stores and

LAUREN MERKIN: $295 Tatum clutch in textured brown available at OTTE 121 Greenwich Ave. NYC (212) 229.9494
ALEXIS BITTAR: $255 large Miss Havisham gold bangle available at ALEXIS BITTAR 465 Broome St., NYC (212) 625.8340
LEE ANGEL: $110 Style #CDN400 12K gold-plated necklace with ivory cabochon stations available at

Belted blouses
MIGUELINA @ LOEHMANN'S: purple silk blouse $54.98 available at retail stores (212) 352-0856
ANN TAYLOR: $119 tweed pant Margo fit Style 22441 available at Ann Taylor and

EXPRESS: $44.50 pewter belt with pearls & tassel available at Express retail stores,
, call 1.877.414.4551
ZAPPOS.COM: $89 MIA menswear-inspired oxford bootie style: Sloan available in plum patent and black patent at
CYNTHIA ROWLEY: $425 Ginny Too large black leather tote with side zippers and buckle detail available at

ALEXIS BITTAR: $375 Lucite quilted cuff in light gray available at Alexis Bittar, 465 Broome St., NYC (212) 625.8340
LEE ANGEL: $160 silver landscape pendant necklace style # EMN426 available at

Q: I'm 5-foot-3  and petite but not curvy. I love my new riding boots — tall and just a one-inch heel! I wear them with long skirts to work, but am I too short and/or too old to tuck in my pants at work or tuck in jeans on the weekends. Any suggestions? And how do you keep them from riding up after sitting for a while? — Shelly, South Bend, Ind.

Dear Boot Tucker, It is your height, not your age, that makes wearing a flat boot with a high shaft (where it hits the leg on the top of the boot) a problem. Wearing them with long skirts creates more of a problem. Here's why: We lose your entire leg line, which is only going to make you look shorter and squatter. We are always going for a short-torso, long-leg body silhouette. Think of Barbie —  just her body proportion, not the hair or the boobs … There's no leg on you at all in a long skirt and if you tuck jeans into boots, you visually cut the line of the leg, making it appear as if you are standing in a bucket. 

If you are under 5-foot-4, I strongly recommend wearing boots only as high as the middle of your calf to maximize the length of your leg line. Wear them with shorter skirts and opaque tights so that we see more of your legs. You'll still be office-appropriate and look a lot longer and leaner, even taller. And while you may not want to hear what I have to say next, tough. You asked. I would take the boots to a great cobbler and have the top cut down so they are not so high on your leg, maybe around two inches. They will still look like riding boots but they will look better on you. And honestly, isn't that what it's all about?

As for your pants riding up, stick ’em in your socks before putting the boots on. Should last you all day.

Tucking boots in jeans
ZAPPOS.COM: $231 Matisse fashionable riding-inspired boots style: Rancher available in brown and black at
JOE'S JEANS @ ANTHROPOLOGIE: $174 Cigarette dark-wash denim available at Anthropologie retail stores
1.800.309.2500 for locations
H&M: $34.90 floral-printed sheer top available at H&M retail stores
UNIQLO: $49.50 Extra Fine Merino V-neck Cardigan available in a variety of colors at 1.877.4UNIQLO or
NINE WEST: $55 "Christobal 30" teal leather tote available at

GERARD YOSCA: $165 red glass stone, pearl, and gold chain necklace available by calling Gerard Yosca Jewelry (212) 302.4349
GERARD YOSCA: $105 purple glass stone stud earrings available by calling Gerard Yosca Jewelry (212) 302.4349
ALEXIS BITTAR: $225 scalloped onyx ring in gold available at Alexis Bittar 353 Bleecker St., NYC (212) 727.1093
SIBILIA: $120 copper and gold bangles (part of a 5-piece set with/turq bangle) available at

Q: I'm a suburban stay-at-home mom with two school-age kids. What type of boots would you recommend that are comfortable, versatile and will stay in style for the long run? I'm thinking equestrian boots with a two-inch heel. What do you think?Francesca, Atlanta, Ga.

Dear Momma Bootie, Same rules as above are going to apply to you. Your height should determine the height of your boot. As I mentioned above, the most flattering height is somewhere around mid-calf; a bit higher if you are taller. If you have a larger calf, remember that a good cobbler can often put in an elastic vent, or purchase boots that have a side zip as well as lacing up the front or a back lace-up vent.

A two-inch heel feels right to me, but if you are running around with two school-age kids, don't feel you half to go quite so high. Maybe an inch and a half will be better for an all-day shoe.  Again, that does depend on you. If you have a higher arch, a higher heel may be more comfortable for you than a lower one. Make sure, whether you order shoes online or buy them in a store, to stand and walk in them for a bit to determine which heel height feels best for your lifestyle and activity level.

Q: My friend just gave me a pair of amazing brown leather, just-below-the-knee vintage boots. I really want to wear them, but do not know how. Do you have any suggestions for a classy outfit?Jessica, Baltimore, Md.
Dear General Boot, Well, that's a supercool friend, I must say! But you don't include much information about yourself with this question, so as before, I refer you to the above answers! But as far as cool outfits, go for a casual look. I love a feminine blouse and oversize cardigan with a straight-leg jean and boots. It's an easy take that still looks stylish and put-together. It is flattering on almost all body types, as you can camouflage a tummy, heavier arms, even a heavier leg because the boot can help to compensate for a heavier thigh.

Q: You indicated that pantyhose were no longer proper attire. You stated that in summer, go with bare legs and in winter, wear tights. I enjoy wearing pantyhose and want to know if I am "old-fashioned" if I wear them. I am 75 years old, a size 12 and am told I have great legs. Please let me know if I am "out of the loop."Shirley, Ontario, Canada

Dear Out of the Loop! At 75 years old, you can pretty much do whatever the heck you want, especially with great legs. (Hubba-hubba!) I did not mean to indicate in my last segment that pantyhose are no longer appropriate attire. My feeling is that those that are considered "day sheer" or "mid-denier" don't look modern, but a bit dated. The "denier" number on hose shows you how sheer the stocking will be. The lower the number, the more sheer they are. 

For example, a denier of 10 will be supersheer. These are great for evening, especially with a little shine or a back seam, as they look natural and simply enhance the legs for evening. A denier of 30, is what I have most trouble with; it's neither here nor there. It's not sheer. It's not opaque. You know? It's like a relationship: Either you're in or you're out. This wishy-washy sheerness dates an outfit to the ’70s or ’80s, when this style was most popular. But when you get to a denier of 50 or above, and the stocking is clearly opaque, I think this becomes a more modern and relevant look. A shiny tight like this can be used for day or evening. The shine is a great visual contrast to a tweed skirt, or wear it with a cocktail dress to keep warm while the shine says party! And by the way, you aren't out of the loop at all! Go on with your great legs!

Mid-sheer stockingsTAHARI @ MACY'S: $119 contrast-trim skirt suit available at Macy's department stores nationwide and
LEGG'S: $4.99 sheer black stockings available at CVS stores
EXPRESS: $59.50 ivory silk cowl-neck top available at Express retail stores,
, call 1.877.415.4551
ALDO: $80 black open-toed suede pump available at ALDO retail stores nationwide
DESMO @ LOEHMANN'S: $149.99 red patent tote available at retail stores (212) 352-0856
LOUIE LOUIE @ NOT ANONYMOUS: $198 purple crystal stone and brass wire necklace available by calling (212) 997.3512

Nude stockings with back seam BANANA REPUBLIC: black lace halter dress $175 #606492-00-1
AGENT PROVOCATEUR: nude stockings with backseam $50
NINE WEST: $89 PAWS red satin peep-toe pumps available at Nine West retail stores and

ALDO: $35 oyster metallic clutch style: Casa Prota-82 available at ALDO retail stores nationwide
LEE ANGEL: $220 12K gold mosaic bracelet with ivory cabochons Style #CDB105 available at

Opaque tightsANN TAYLOR: $99 Petunia cartridge pleat sweater dress style #226526 available at Ann Taylor retail stores and
WOLFORD: $65 Satin Deluxe black opaque tights available at NYC Wolford Boutique (212) 327-1000 and finer department stores
GUESS @ DSW: $79.95 black patent pumps available at select DSW retail stores
MAXX NY: $128 Del Posto Croco Clutch 100% Italian glazed croco available in black, kiwi, purple, gray at

BETSEY JOHNSON @ BLOOMINGDALE'S: black patent belt $40 available at Bloomingdale's department stores or call (212) 729-5900
RJ GRAZIANO: $72 gold-plated and black enamel bamboo bangle call (212) 685.1248 for availability
RJ GRAZIANO: $38 gold-plated bangle with strands of gold balls call (212) 685.1248 for availability
RJ GRAZIANO: $75 gold-plated and bone enamel bamboo bangle call (212) 685.1248 for availability
RJ GRAZIANO: $75 gold-plated and bone enamel bangle with gold studs call (212) 685.1248 for availability
LOUIE LOUIE @ NOT ANONYMOUS: $198 black crystal and brass wire necklace available by calling (212) 997.3512

Q: I was so surprised to see Matt say he'd be doing the style segment last week that it made me take a second look at what he was wearing — and then promptly cringe when I saw him wearing a black suit and brown shoes. I had just convinced my guy friend at work that he was violating all sorts of fashion rules and I was making such progress (no more Hawaiian shirts and checkered blazers!) and had almost convinced him that you can't wear black with brown shoes ... and then there's Matt! Did I miss this — can you mix black and brown? Or are there just different rules for guys?  — Jodie, Malden, Mass.

Dear Male Style Expert, While I commend you for getting your friend out of Hawaiian shirts and checkered blazers, I can't say that Matt ever commits style faux pas on that level …  Except for the awful stone-washed jeans he wears on location without socks (don't tell him I said that). But I say that Matt is a style icon (Vanity Fair thinks so, too). Matt was actually wearing a dark blue suit, which is perfectly acceptable with brown shoes. Gray suits look great with brown shoes as well. It's not unheard of to wear a black suit with a brown shoe for day (though difficult to pull off). But the belt must match the shoes, and I recommend adding a shirt, tie or pocket square that has a print with both black and brown in it to marry the color combination and create a deliberate and cohesive outfit.