I’m obsessed with this matching set from Ann Taylor. The key to dressing well if you gain weight is simple: buy bigger clothes. If you’re a person whose weight fluctuates, you have to honor your body at every size No point in trying to put ten pounds of sugar in a five pound bag. The best part is, all these items are on sale LTKWorkwear LTKootd

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The Clean Pencil Skirt in Plaid | Ann Taylor
Belted Vest in Plaid | Ann Taylor
Tony Bianco Asti Slingback Pointed Toe Pump in Bordeaux Patent at Nordstrom, Size 6.5 | Nordstrom
Fitted Non-Iron Stretch Supima® Cotton Dress Shirt | Brooks Brothers
Men's State Solid Tie, Macy's Exclusive | Macy's
Asti Slingback Pointed Toe Pump (Women) | Nordstrom
Plaid Fitted Long Blazer | Ann Taylor
The Sophia Pant in Plaid | Ann Taylor
Plaid Pleated Skirt | Ann Taylor